Origins

I also had aspirations to be a professional musician. Music has been a consistent thread throughout my life. Although I never broke into fame as a musician, I have a home studio and I’ve written and recorded four albums in the past three years. Music is a great creative outlet for me.

You started a computer science degree, but have said that writing software for an ATM in C killed your interest in programming. Why?

It didn’t kill my interest in programming, but it killed my desire to work as a programmer. That course showed me just how boring and not challenging programming could be, and I thought that that was going to be my future if I continued down that path. But I never stopped programming, and I never stopped teaching myself new things.

After that, what was your ‘eureka'  moment—the one that, if you look back on it now, re-ignited the interest in working as a programmer?

When I was a little kid my dad worked as an engineer for a manufacturing company. They had a mainframe there, and in his free time he would play a text-based game called Adventure. The mainframe didn’t have a display, so all of the output went to this green striped tractor-feed paper. He would bring the printouts home, and I would spend hours reading through his game.

One day in summer I was inspired to create my own game. I took a pack of index cards and a ball of yarn and set to work recreating the game he had been playing. Every index card was a room, and the exits from the room or actions that you could take there would lead to another index card that I connected with tape and yarn. When my dad came home from work he found me in the middle of this network of cards and string that had taken over the entire living room. That’s when he decided we needed a home computer.

I spent endless hours growing up playing and programming games. In my post-college years I got a hand-me-down computer from a friend and it had a modem. I started hanging out on BBSs and in 1993 got on the internet for the first time. I discovered MUSHes, which are like text-based MMORPGs (Massively multiplayer online role-playing games), and started programming games on them.

When my dad came home from work he found me in the middle of this network of cards and string that had taken over the entire living room. That’s when he decided we needed a home computer.

A pivotal moment for me was when I read a book called “Gödel, Escher, and Bach”, by Douglas Hofstadter. The book deals a lot with artificial intelligence, and this really sparked my interest. So I started conducting AI experiments in the MUSHes that I ran. For example, I built an expert system that could answer questions about Egyptian mythology. It was set up like an interactive museum and the curator was the program that players interacted with. But objects that you can interact with in a MUSH, like a book or a car or a telephone, are limited in size, for both code and data, and there wasn’t enough room to make the curator smart enough to understand and answer questions. So I cheated by storing code and data in the various artifacts scattered throughout the museum, and wrote a networking protocol that allowed them all to talk to each other. Basically a distributed neural net. I was pretty proud of that.

I also created programs called ghouls. Since MUSHes are all text-based, human players interact through emotes and typed text. My ghouls posed as fellow players. They would wander the world until they came upon a group of two or more human players, and they would listen to the interactions between them. Then they would go off in search of other players, and selectively play back bits of the conversation, things like saying hello and asking what you were doing or whatever. When they got an interaction in return, they would score a “point”. Those points were like food: too few points and a given ghoul would die. If two ghouls with enough “points” came across each other in the world, they would reproduce and spawn a new ghoul with their collected memories. Essentially I was writing code to solve the Turing Test. They were primitive but they were interesting.

Describe your career path, either from or around that moment. What events, random or connected, brought you to Stitch Fix?

I was an early adopter of the internet. In 1994 I was working for an engineering company in Austin, Texas. The job was pretty boring, tracking press releases for the marketing department. But I knew all the other geeks at the company and we would spend our breaks together just chatting. One day a guy that I knew came up to me and said that the company was thinking about building a web site and was putting together a team to work on it. “That’s cool,” I said. “It would be great for the company to be online.” He smiled and said, “What do you think that will do for your career?”

That was the first paying software job of my career. I remember being really stressed about the interview, studying HTML to make sure that I wouldn’t mess anything up in the evaluation. It turned out to be really easy. The web project was great, too, because we ended up setting up a lot of automation between our technical writing team and our web content to publish data sheets on our products. So it wasn’t just straight HTML, it was much more involved development work.

Do you ever feel pressure to be a mentor, an example, or a role model for other underrepresented folks in tech?

I don’t feel pressure exactly, but it’s something that I’m passionate about doing. There have been people in my life who helped me get where I am today, and without whom I would never have had the chances that I’ve had. I hope that I can be that person for someone else, too.

Tech careers can be so transformative. The work is interesting, the potential for personal growth and development is huge, and the pay is ridiculous. Marginalized people especially deserve to have access to this kind of life-changing career. We face a lot of hurdles and we have to be 150% better than our peers just to survive. If I can help someone not just survive but thrive, I’m going to do everything in my power to do that.

I have a lot of privilege, owing to being white and upper-middle-class and very well established in my field. I try to leverage my privilege to make things better for other people.

At some point there’s a scaling problem, though. I can only mentor so many people one-on-one. That’s why I look for other opportunities to give marginalized people a hand up. I have a lot of privilege, owing to being white and upper-middle-class and very well established in my field. I try to leverage my privilege to make things better for other people. Some of that comes from just being a visibly successful woman (and a queer transgender woman at that.) Some of it comes from working within my company to improve our culture, to make it more inclusive and welcoming. Some of it is in the community, through my volunteer efforts with nonprofits, or my side projects, like the Contributor Covenant, the Post-Meritocracy Manifesto, and Open Source for Women. And some of it is taking my Silicon Valley money and giving it to organizations like Black Girls Code who are working to make a difference in the lives of marginalized people.

You’re prolific when it comes to building those initiatives and side projects — not to mention the Greater Than Code podcast and open source contributions among others. Where do the ideas come from?

It might sound weird, but my main motivation is guilt. I feel blessed to have achieved what I have, to have this position in the community, and to have the kind of influence and opportunities that I do. I want that for everyone, and if I’m not actively working on making that happen then I start to feel bad and look for new ways to change the world. I try to understand the challenges facing people getting into our field, struggling to stay in it, and think about ways that I can leverage my privilege to help them. 

I also think that I have a responsibility to make other people with the same or more privilege than me aware of their responsibilities to the community and the industry, to the impact that they can have on other people’s lives. I’m a born problem solver, and there are so many problems that we face today that I’m never short of inspiration.

How do you continue to find time for those things, especially when it comes to balancing a family life and maintaining your mental health?

I’m by nature a very disorganized person, so over the years I’ve developed systems that help me remember things, track my goals, and answer the question “what do I do next?” I even open sourced it! My system keeps me organized and ensures that I always have a place to jot down an inspiration or idea, and not lose it. It makes me very efficient, which is what lets me work on so many things at the same time: a challenging job, my music, open source, advocacy work, nonprofit board responsibilities, my D&D campaign, and the book that I’m co-authoring.

If you could do everything all over again, do you think your journey would be the same? Would you want it to be?

I made some serious mistakes along the way. Until the past few years I didn’t have good boundaries between work life and personal life. I was an overachiever and I would regularly work 60 or 70 hours a week. I missed out on a lot of time with my daughter, my friends. And I really regret that.

So much of my success was luck, I don’t know if I could be that lucky twice.

In terms of my journey, so much of it was serendipitous that I’m not sure that I would end up in the same place if I did it all over again. So much of my success was luck, I don’t know if I could be that lucky twice.

Is there anything about the internet or technology that you feel nostalgic about? What has changed most for you since those early days?

When I first got on a BBS and used an email client to send messages to someone on a completely different BBS, I thought it was pure magic. Then I got online and experienced the web and IRC and news groups. For the first time in my life I was able to find and connect with people who were interested in the same sorts of weird things that I was. And I started learning a lot about my internal struggles with gender, that I wasn’t alone. I really wonder how different my life would have been if I had those kinds of connections and access growing up.

How do you see your next five to ten years? What are you most excited about? Perhaps most afraid of?

As I mentioned I’m currently writing a book with my friend Naomi Freeman. It’s called The Compassionate Coder and it’s a guide to practicing empathy in software development. That’s taking up a huge amount of time and effort. Once that gets published, I’m looking forward to getting back to one of my side projects, an AI program called Sophia. My goal is for Sophia to be able to understand and create metaphors and similes, and as a side effect I think she will learn how to pun. I’ve been fascinated by AI for twenty years now, and I’m looking forward to learning and doing more of it.

Aside from that, I hope to continue speaking at conferences (maybe with more keynotes?), keep learning new things, do my advocacy work, and find new ways to help people. Because that’s what I care about more than technology-- people.

Is this where you expected to find yourself when you were a kid? If not, where did you think you’d be?

When I was young I wanted at one point to teach primates how to communicate through sign language. I recall learning of Washoe and Koko, and this fascinated me as I studied psychology. Younger me wouldn’t have imagined I could do what I do, because what I do simply didn’t exist then. Now, I’m glad it is.

Younger me wouldn’t have imagined I could do what I do, because what I do simply didn’t exist then.

What was the moment which sparked your interest in tech and user experience design? What about open source?

The first ever application I got to work on was as a Java developer. I was working primarily on the front end, we didn’t have a designer, and it fell to me to do it as I had an art background. I remember delighting in mapping out the user flows and taking my first steps into user research. This was the 90s, though, and UX design didn’t exist as it does now. In most cases, technical roles were developer-only. At this point, I saw that you could do both sides, and this set the foundation for what being a designer means for me.

The denser the architecture, the more interactions, user journeys and options, the happier I am.

When I began working on more complex sites, I began to see where I really enjoyed working: in the complicated experiences, and creating communities around them. The denser the architecture, the more interactions, user journeys and options, the happier I am.

Open source to me was and is something that makes sense, fits my worldview. It enabled me to learn, to grow and get to the career I now have. Product-wise, I began using Linux software out of a need of affordability. My journey to WordPress started by someone suggesting I use that over my own system, which was stuck together with little more than hope. There wasn’t really one single moment– I moved from a user into a contributor and saw the power of giving back what I had gained.

Describe your career path, either from or around that moment. What events, random or connected, brought you to Automattic via psychology, art, design, and front end development, in whatever order?

I have had quite a long trip to get where I am. As I said earlier, I began studying psychology, then changed to art. I tried to be an artist, doing painting, photography and performance poetry, and I got to perform at Glastonbury. After a few years, I was given the opportunity to study software engineering as part of a government scheme to get people back into education to learn tech, whilst I enjoyed doing art, I felt it wasn’t going to pay the bills.

Even in my art, though, I had always been technical. For example, my preferred forms along with paint, were photography and video. My inspiration was wide-ranging, from Bill Viola to Stelarc. Throughout my education, it was assumed that you couldn’t be into art and engineering, but I was.

After university, I had a short game development career which included working on tools for developers, this led onto various technical roles. I then worked in an agency as a designer, then in publishing on print design using Quark and InDesign. As the web grew, I found myself moving into that, taking on more and more front end development both in my work and spare time. Eventually after progressing through agencies, I moved into freelance full time. Over time, I built up an unplanned specialisation in community design, focusing on creating sites that had a community aspect.

Throughout my education, it was assumed that you couldn’t be into art and engineering, but I was.

I was freelance for a long time. I was contributing in WordPress on a community level and pretty happy with my lot. I was asked a few times if I was going to apply to Automattic, but I couldn’t see a place for myself there, mostly because I was happy where I was. But then I was invited to speak at WordCamp San Francisco. I nearly didn’t go, but thankfully (due to support) I was able to. I talked to people about where I could fit into Automattic and from there, the rest just...happened. Timing wasn’t great— I was writing a book, running my own business and organizing WordCamp Europe. But it all worked out and though I wouldn’t recommend juggling so many things, it did change my life for the better.

Whilst I felt I fell into things, everything synchronized beautifully for me. I was around at the right time for the web and for user experience design. I also was always involved in communities, from numerous forums, blogging networks such as 9rules, and linux IRC communities— so the foundation was there.

You’re passionate about the communities we create online; what sparked this passion, and what prompted you to become more of an advocate for inclusive design as a practice?

Communities and belonging to them has been a thread throughout my life, even down to the software I chose and open source communities I take part in. That belonging has enabled me to get where I am today: that’s powerful and something I don’t forget. On the web, we have this ability to support, enable and empower so many more to be part of a community.

I have had both good and bad experiences online, like most people. I remember a time when it was hard for a woman to use their real name online, because they got the ASL (age, sex, location) message avalanche. This adds to my drive to create better inclusive communities and fuels my passion for inclusive design. Online we have the potential to nurture and enable so many, but we have to be mindful how we do this. Community design is a specialization which focuses on that.

Online we have the potential to nurture and enable so many, but we have to be mindful how we do this.

Last year, I heard Kat Holmes say something which continues to resonate with me: “We are temporarily able bodied”. As I am now over 40, that rings so true. The web community is ageing, and we live in an uncertain world. This means that more and more, we need to enable people with the experience we create. The web should be for everyone, but it’s not. Making it so is incredibly crucial.

A psychology question: Do you think empathy is necessary to practice inclusive design? Or simply an understanding of our own limitations?

I do think that empathy is necessary but I think we need to remove some of the weight and misconceptions we have about it. It’s about understanding: you aren’t expected to feel everything someone does, but you can understand and listen to their story. As designers we should spend equal time listening and doing. Being empathic isn’t enough. You have to act on and make it part of your process.

You start with yourself in any understanding, because we are all human. But this is a starting point, not a limit. If you create just for you, that’s pretty limiting. Moving beyond your headspace is the important next step. I think everyone can learn this, and all those involved in making a product should develop it.

Do you ever feel pressure to be a mentor, an example, or a role model for other underrepresented folks in tech?

As I’ve grown older, I don’t feel pressure as much as a yearning to do so. For a year or so, I’ve taken part in the https://mentoreverywhere.com/ program at Automattic. Through that, I’ve mentored two amazing women who have taught me so much: how difficult our industry is to get started in, as well as how to recognise the skills I have gained along my way. Mentoring is a two way process.

I truly don’t see myself as a role model, so answering that part is hard. I think we often pressurise ourselves too much in this industry, adding too much weight to everything we do. As a result, we create a pressure that may not even be there. I see this often. Sometimes we just need to be easier on ourselves, let ourselves be who we are and not strive for super powers.

Overall, though, so many amazing people have enabled me throughout my life, so anyone I can enable is a tiny part towards repaying that and passing the gift on.

Is there anything about the internet or technology that you remember from your childhood/early years that makes you feel nostalgic?

One tech toy stands out. It was called ‘Mr Professor’, a math calculator that you could learn from. This was before most homes had computers, but this toy appeared in the mid-70s, and it had a captivating experience. If you look at it, it’s a pretty amazing design: the attractive form, robust build quality, made to engage but survive being used by children. The actual program on it was really well thought out and really did help to teach some pretty advanced math concepts to really young children.

How do you see your next five to ten years? What are you most excited about? Perhaps most afraid of?

I am excited for where open source can go, for the stories of contributors to WordPress that haven’t been told yet. I truly think that the future is open source. It can enable and empower so many more people than closed products. As far as being afraid, the state of the world right now is pretty bleak at times, but I do have faith in the human spirit. I think even in the bleakest time people come through and I can see that happening as we move out of a time where it feels like every day is a new emergency headline.

Thanks for your patience and thought, Tammie! It was a pleasure! 

Have you gotten any responses that you’ve been surprised by, good or bad?  

I’ve only had one negative experience, and that was just someone who wanted to force me to apologize for something I wasn’t going to apologize for, so she got really belligerent. But even when there is pushback, I can frame my response in a way that prompts them to reflect, and people often say, “Oh, your approach made me safe enough to think about this and I recognize that my response was not thoughtful.”  Sometimes on Twitter, you miss the nuances of communication, though, and I really try to craft my message. For example, a guy pushed back against one of my Tweets and I responded, but I didn’t engage him in conversation because I didn’t think it would be a productive conversation.

Did you set out to engage in these conversations? 

This was not a planned approach— I kind of fell into this. But because of the background and experience I have, I am perfectly able to have these complex conversations in a unique space. I do a lot of conferences, and my third or fourth slide is always my credentials, because I know that someone in the audience is already thinking, “Why should I listen to this Black woman?” Last year I did 19 conferences, keynoting 5 of them, and I felt like I’d earned my right to be on that stage sharing my opinion. 

But I shouldn’t have to earn that. I have a masters degree. By the end of the year, I will have a doctorate in business administration. I know this shit. Many underrepresented individuals don’t have these credentials, and it enables me to say what I need to say and shut a lot of stuff down, without people questioning me. 

my third or fourth slide is always my credentials, because I know that someone in the audience is already thinking, “Why should I listen to this Black woman?”

I’m also very adept at guiding conversations, because I’ve been a high school teacher. I’m used to reframing the conversation and bringing us back to the problem. I recognize defensiveness, attempt not to take it personally, and I structure my comments that allows me to say what I have to say, with an exclamation point, and I’m done. I control it.

What are some of the biggest problems or misconceptions you’ve encountered?

How people don’t understand how privilege affects marginalised people. I like to start with a definition of underrepresented and marginalized. Underrepresented is about numbers: there aren’t enough people. Marginalized people have been treated unfairly, and this doesn’t include white women. While they aren’t treated like white men, they still benefit from privilege, and until we can have an honest conversation about that, it will continue to be a big issue, particularly in the Black community and communities of colour. We say “We’re making progress with women in tech,” but we’re making progress with white women. Everyone else is falling behind. You invite a population of people who have already been mistreated into a community that continues to mistreat them, and they will leave. 

We say “We’re making progress with women in tech,” but we’re making progress with white women. Everyone else is falling behind.

You cannot be my ally until you allow me my truth. White women historically have used their privilege to fall back on, and I don’t have that luxury. So when you say you’re an ally but you respond to me and make it a personal attack, how do you not see the disconnect there? I say this in my talks when I’m talking about white men who are my allies; I call them my League of White Men. They appreciate my honesty, and they have the keys to everything, so why not use them? Why should I break the door down when they have the ability to open it. I’m not blaming them, but I am holding them accountable. They didn’t create the system, but they do benefit from it. 

You cannot be my ally until you allow me my truth.

Why do you think we’re so focused on finding someone to blame, rather than trying to re-learn how we speak about these things? 

I can’t answer that, but what I’ve observed is that, in work disagreements, when the Black woman or person of colour doesn’t back down, they’re “being aggressive,” or “being defiant.” White women seem to fall back on emotion, thinking that we’re attacking them. They become intimidated and scared. That reminds me so much of Jim Crow. What it unconsciously communicates is a showcase of privilege. I have some wonderful white women who are my allies and they recognize that they do this. But they look at my videos and go “oh shit, I need to make sure I’m not doing this.” It’s not about blame; we’re not going to get the perspectives we need to improve our communities and organizations without listening. Right now there’s a lot of “you can talk, but don’t say that.” 

At conferences, I talk about being a female in the south, and received feedback that I was “politicizing it.” It’s like inviting someone into your home and treating them like shit, and then wondering why they’re grabbing their coat and getting ready to go! 

[Difference in perspectives] matters for ROI; it’s not political, it’s business.

And that’s just talking about gender and race. There are all kinds of other perspectives — people with disabilities, LGBT people. You have to at least have some perspective of their experience to create products and services for them. This matters for ROI; it’s not political, it’s business. CEOs don’t have to care about inclusion and diversity, but they can put the structures in place and get out of the way to allow the employees and partners and the people who do care to make something great. The CEO doesn’t need to understand or care about diversity to throw money at it and watch it do great things. You’ll see your customer base change, your employees change, your profits change. THAT will change the CEO’s mind. It’s about operationalizing diversity and inclusion. If people don’t have the resources or autonomy to drive change, then what have you done?

CEOs don’t have to care about inclusion and diversity, but they can put the structures in place and get out of the way

Sometimes, the best thing we can do is just get out of the way, and resist the urge to throw tech at everything. 

So many people in this space do not have that skill. I hate the term “soft skills.” If my talk is related to tech, it’s a technical talk. I have very technical skills, ones that developers and UX designers do not have. My ability to communicate with people is devalued because I’m not writing code. If your only skill is coding, then you’ll be obsolete very shortly. There are other skills that you need to have: critical thinking, problem solving, and if you can’t do that, then there’s no need for you. The people with my skills will always have a job in this space. Humans will always need to be navigated.

Is navigating this space this where you expected to find yourself when you were younger? 

Hell no! This didn’t even exist when I was a kid. I’m 49 soon, and call myself a proud multipotentialite. Growing up, I’d do something, get good at it, and move on to the next thing. People thought I was flighty and unfocused, but that’s helped me a lot. 

I never saw myself as a producer of tech, but I just solved my own problems. 

I’ve always been more than your typical consumer of tech, but I’d never seen myself as being a producer of tech because nobody in my community was talking about that. Although I had a computer before a lot of people I know, a lot of that came out when I was adult. I have an undergrad in interior design, so I used CAD in the 90s. When the new tech came out, I would buy it and be interested, but not just as a toy. Specifically, when Apple would have their keynotes, I watched the developer one because I liked hearing why and how they made what they did. When I wanted to build a website, I would google how to make one and follow Youtube videos. I never saw myself as a producer of tech, but I just solved my own problems. 

So what made you take the leap? 

In 2014 my dad died, and that was my greatest fear— dealing with the death of a parent. At the time, I was a teacher, but I was not happy. I thought, “OK, my dad died, I didn’t. Fuck it, I’m going to do what I want. I’m ready to stop being scared and jump off the cliff.” I went to Maui for a week after the services and I sent a text to a friend: “I’m leaving education and I’m going into ‘tech’” . The “tech” was in quotes, because I had no clue. I just thought I’d figure it out.

When I came back, being a Black female in the south suddenly became an advantage because people wanted me to go to these tech events. When I went to my first Javascript conference I didn’t even know what Javascript was. In theory, my next step should’ve been to learn to code, but I didn’t. As an educator, I have a real problem with how we teach coding, especially with underrepresented and marginalized people, because we’re spending money on programs that don’t work. When it comes to teaching, we need to teach computational thinking, and then allow people to go into whatever area of tech they choose to. 

My first talk was at ScotlandJS in Edinburgh in 2016, and I did 2 or 3 more that year. I was figuring out that I didn’t want to code, but I had skills, and was finding how best to communicate that people were missing the boat. At that point, I was working on my doctorate, and I sat down every Sunday and at minimum filled out 10 CFPs. There were many I didn’t get, but by sheer numbers, I caught a few! I started going to Python, Clojure, Angular, Ember, Ruby conferences, DevOps days. 

All of a sudden, I became this inclusion and diversity person and I was really pissed about what I was seeing. People want to hear me talk, but they don’t want to pay. They want consultancy, but they don’t want to pay. This goes with the hashtag I’ve been using, #causeascene. I’m passionate about bringing underrepresented and marginalized people to the business table. We need to stop being reactive, like with #TakeAKnee and #MeToo. These issues matter, but what is the strategy for effective change? You get outraged, and then you don’t hear about it once something else is in the news. People get upset, but nothing changes. Instead of being outraged and reactive, I want to be strategic and proactive. We need underrepresented and marginalized people people at the business table, so we need to teach them about business strategies. That’s what @biz4socialchg is: helping underrepresented and marginalized people understand the structures and systems that need to be in place to grow a business so that you can be at the table and you cannot be dismissed. 

Was there a specific moment when you decided that this business-based strategy was what you wanted to hone in on? 

Recently! When I grasped the business focus, the puzzle pieces came together and I realized I had a unique perspective. I saw that we could improve our communities and orgs by applying business practices. The open-source community is not sustainable. Node, for example, is not healthy right now. It’s blown up on Twitter a few times and at some point, there’s going to be a moment where the stuff you’ve ignored is bigger than the stuff you can save. There will be a tipping point when the codebase starts reflecting all of this, and that means you’re not getting enough issues, enough pull requests, enough people from enough backgrounds looking at the code. This creeps into the code of all of the organizations using node, and affects their business. The lack of diversity will have a ripple effect throughout tech. The issues may not show up in the codebase today, but business leaders will see them in a few years when it impacts their customers’ experience and their data, and they’ll be liable. 

Now that I’ve realized that’s where I can create change, I’m so excited about it. What I want to do is make business school education available to the masses, particularly so that underrepresented and marginalized people can build scalable businesses.

Do you ever feel pressure to be a role model in the way that you are? 

I would if I hadn’t had my experiences in education. Particularly being a special-needs teacher, I had to take on a family role as well, educating families on the system and how to maximize that system for their child. I really believe in self-care, because this space can be very toxic and I have to make sure my mental and physical health are paramount. At the end of last year, I was neither happy nor right, and now that I have found the space, in tech, that works for me, it's easier for me to focus on me.

This is especially true as a Black woman in the United States. People don’t realize just how much of the country’s success has been achieved on the shoulders of Black women. I no longer am the “strong Black woman.” I used to take pride in that because I thought it meant something. But now, I know it’s an excuse for people to use me. I am very aware if I don’t want to do something, and I’m honest about it.

With this new outlook of yours, how do you see your next five, ten years? What are you most excited about or afraid of? 

At this point, I’ll be 50 in a year, and “no” doesn’t exist. I’ve been saying this a lot recently: I don’t care what your opinion of Trump is, but you can’t say he’s not confident. I gave myself permission to be confident, but I balance it with empathy in all the other skills I have. That level of confidence has allowed me to say “fuck it” and just do what I want. I unapologetically take up space, and it’s so freeing and cathartic!

I gave myself permission to be confident, but I balance it with empathy in all the other skills I have

I don’t have many fears. They’ll find me, so I won’t focus on them. But before, when I was speaking, I got burnt out quickly— five countries in a month! I look forward to traveling the world in a way where I can go to these countries and enjoy them, and not get right back on a plane. I want to enjoy my life! I just want to have fun. This is one industry where people can make a shitload of money, and I want my part of it, and I want to enjoy myself. I add a lot of value to the community and I want to make sure I’m living my best life.

Thank you, Kim, for your time, thought, and invaluable insight. It was an honour to chat with you! 

Do you miss coding day-to-day?

I still end up writing a little bit of code most days, usually ad-hoc data munging and aggregation jobs. And I code in my spare time. I miss the relaxing expectations of being a pure coder, where your job is to write a piece of software that does a thing and you can be sure the thing is done because it works. Running a startup, you’re never certain if you’re finished, and you don’t know until years later if it was the right idea.

I’m assuming that this is not where you expected to find yourself when you were a kid. What did you expect to be doing “when you grew up”? What did others expect from you?

The funny thing is that this is pretty much exactly where I planned to be. When I was 16 in 1996, Yahoo.com was one of only a handful of really professional, big websites. I clearly remember looking at it and thinking “damn, I’d really like to work for them, but they already have a website, they probably don’t need more developers.” That same year, pondering my future, I also decided I would like to run a company. “Probably not CEO, but, like, second in command,” was how I described it to a friend. 20 years later, I’ve worked for Yahoo.com as a developer, and am second in command at a startup. I feel very lucky.

My family have always expected that I will become a dot-com millionaire. The fact that it hasn’t actually happened yet is a source of concern for them, in fact.

You’ve written that you became a web developer because the early web saved your life, and it’s a place worth preserving. Can you identify a single moment that brought you to the web, and then sparked your interest in building websites?

The very first website I visited (using Netscape!) was the now-defunct trinidad.net, the website of an ISP in Trinidad. It was quite well designed for the time, and that was amazing to me.

This feature of the web as the great leveler, the great democratizer of communication, still grabs me by the heart.

Growing up in Trinidad, the TV programming is, 95% of the time, imported American cable— which assumes you are American. So I was used to a diet of media that made cultural assumptions I did not recognize: 1-800 numbers I couldn’t dial, toys I’d never buy, and breakfast cereals that I would never taste. I was used to being a second-class citizen, not considered by media. But trinidad.net was a professional-looking website about Trinidad, for Trinidadians, assembled by Trinidadians. The New York Times had a website, and it was no better than trinidad.net. That was amazing to me. In this new medium, me and the world were on equal ground! I could make a website, and people would take me seriously. Nobody would know I was a 15 year old kid from a rock in the ocean nobody had heard of.

This feature of the web as the great leveler, the great democratizer of communication, still grabs me by the heart. I wanted to be a web developer pretty much from the moment I saw the web; within the first 2 hours of using the web, I was making a site.

When it comes to participating in that web community these days, the assumption seems to be that people will (and perhaps should) do so by contributing to open source. You don’t; you do so with your writing instead. Why?

I think engineers assume they should participate in the web via open source software because they are engineers, and that’s what engineers do. Open source code is highly leveraged and very useful and you should do it if you can, but I don’t think of it as the only way to contribute. One should contribute by doing what you’re good at, and while I am a mediocre coder, I am a pretty good writer.

Minorities often not only have to realize that software development is a career path, but is also a career path available to them. What made you realize that this door was open to you, that you could build websites and be out?

I’ve written in the past about why representation matters to me. I’d always known I could be openly gay and work in tech -- there are so many websites about gay stuff, clearly there were gay web developers -- but as I wrote, I’d definitely considered how high I could rise, and how open I could be, to be limited by my sexuality. Discovering that [Fog Creek CEO] Joel Spolsky was both a respected tech commentator and openly gay changed my mind about how high I could rise in this industry. But also I think I’m just the kind of arrogant dick who would think he could just do whatever he wanted, so maybe it would have happened anyway 😉

Describe your career path; what events, random or connected, brought you from Trinidad, to the UK, to npm and San Francisco today?

The start of my career was building websites in Trinidad with my friends. In 1996 almost nobody knew how to build a website, so a bunch of 15 and 16 year olds approaching established companies saying “we’ll build it for you” was, in that very strange time, a totally plausible thing. My mother used to have to drive me to meetings, because I didn’t have a license.

When it came time to go to college, my parents only considered the UK— my mother grew up there, and there no respectable colleges in Trinidad at the time. I took a “gap year,” initially intending to to travel around India, but I started in London to earn some money beforehand. The dot-com boom was in full progress— I quickly got a job at a startup as a web developer, and I stayed.

My mother used to have to drive me to meetings, because I didn’t have a license.

January of 2000 was an absurd time to be a web developer. Talent was in short supply and budgets were huge. My interview consisted of opening my laptop and showing them a website I’d built, and suddenly I had a contract for a huge hourly rate. By September, when it was time for me to enter university, the crash was clearly already coming. My boss, a lovely man called Neville who has been my friend and mentor ever since, told me to get the hell into college and stay there to ride out the storm. It was excellent advice, as nearly all his advice has been.

It was a curious experience getting a job after returning to London with my Computer Science: as a teenaged developer with no degree I was a wunderkind, and could demand whatever I wanted. As the exact same person plus a college degree, I was a new grad, to be paid almost nothing. Suffice it to say I don't think web developers need degrees to be good web developers.

The crash also meant jobs were scarcer. I ended up working at a crappy company with my one and only homophobic boss. Before I even started, they invited me to their “Friday afternoon drinks” where I would meet the team. We got into a conversation about computer games, and I mentioned that I thought The Sims was cool because all of the characters were inherently bisexual -- you could make anybody fall in love with anybody. My about-to-be-boss said “I don’t want perverts in my computer games.” I stayed there for a year, hating every minute of it until Neville once again saved me, landing me a job at a different company.

That next job had its own issues, but it was in the mobile space— in 2005, a good place to be. I got headhunted by Yahoo— the job I’d dreamed about! I was building a website that sold mobile ringtones, back when that was a multibillion dollar industry, at a big company with both recognition and training opportunities! After working there a year, Yahoo did an internal re-org and as part of that, rather than be laid off,I was allowed to apply for jobs at other parts of the company, including San Francisco.

So off I flew to San Francisco! Fellow Yahoos told me where to live (not Sunnyvale!), helped me find an apartment, get a bank account… it was really welcoming. It was here that I met Isaac, at the time just a funny nerd that I enjoyed having lunch with, who had a reputation for being good at JavaScript—  he’d go on to create npm and run the Node.js project. We’d been talking to each other on Twitter, which was just over a year old around then.

I left Yahoo in 2010, and co-founded a startup called awe.sm (pronounced “awesome”) which provided “social media analytics”— unfortunately, its name was its best feature. We struggled for a couple of years, because there was no product-market fit, and I burned out and quit in 2013. I’d saved up enough to take a year off, so I did.

Meanwhile, Isaac had invented npm and become head of the Node project. By the end of 2013, npm was so popular that he decided to turn it into a company. We’d kept in touch, so when he was looking for somebody to run engineering, I was the person he came to. At awe.sm I was effectively the CTO, and so I'd stumbled into experience of running an engineering organization through three years of extremely painful trial and error.

There was no grand plan, just luck and happenstance.

I often think about how lucky and random it was that I met Isaac, that we became friends, and that I had no job at the time he needed to start a company. There was no grand plan, just luck and happenstance.

How did you make the move from individual developer to manager? What was the most difficult aspect of that, or was it a natural shift?

I did not, at all, want to become a manager. I don’t think engineering to management is in any way a natural career progression. It was a totally different skill set that I picked up out of necessity.

My npm co-founders Isaac and CJ have aided me in becoming a better manager. Isaac is extremely conscious and deliberate in his use and application of empathy. He’s not a naturally empathetic person, but he practices at it, and has got good at it. As a result, he is a very good teacher of empathy in others. CJ, on the other hand, brings almost 30 years of experience to the job, so there is almost no situation she’s not seen before, and she always provides useful insights.

I also get a lot of “freebies” by having hired a bunch of very capable and extremely senior people at npm. They handle time management and motivation themselves, and need only the coordination from me, which is the easiest part.

For the underrepresented, representation matters. But for some reason, it seems easier for those at the top to be out — they’re “different”, they’re “successful”. Why don’t beginners feel the same freedom?

I think this is just down to stigma and stupid hiring practices. Too many companies hire for “culture fit” but think that means “somebody we want to hang out with after work” (I wrote about this, too!) Hiring for homogeneity like that creates a pressure not to be different, and that pressure is stronger the earlier in your career you are. I think it’s improved a lot in the last 10 years but still very, very far to go.

Do you feel pressure to be out at all, to be a mentor and a role model for others?

I don’t feel any pressure to be out -- if anything, especially with investors, who tend to be very conservative, I feel a pressure not to be. But fuck that. I believe some people have found my visibility as an openly queer and vocally queer person in tech to be encouraging, and that’s way more rewarding than not getting a raised eyebrow from an investor.

If you could do everything all over again, do you think your journey would be the same? Would you want it to be?

Sometimes, I think that maybe I would have skipped the UK and gone to college in the USA. I enjoyed my life in London and made some amazing friends. But career-wise, I should always have been in California. But who knows what else I’d lose doing that?

I would definitely have come out earlier. The consequences were so much less bad than I feared, the relief of being out so much greater than I dreamed. My god, being closeted was so terrible.

Is there anything about the internet or technology that you remember from your early years that makes you feel nostalgic?

My most important and fondest memory is of joining The Youth Lists. There’s so much subtlety in how they’re described that is lost today -- the lists accepted “questioning” (i.e., not yet gay-identified) people, and that was all I was willing to admit to being. The name “The Youth Lists” says nothing about being gay, and that made it easier. The support, friendship, hope I found in those emails from strangers cannot be overstated.

The consequences were so much less bad than I feared, the relief of being out so much greater than I dreamed.

When I say the web saved my life, finding The Youth Lists was the most important part of that. I’ve spent my whole life creating similar efforts. The most recent, the LGBTQ in Technology Slack, has 3500 members today. Myself and Aria Stewart may have started it, but it’s run by a bunch of selfless volunteers and I don’t take care of it day-to-day. The volunteer admins are amazing and don’t get enough thanks. If the Slack group has helped even one person as much as the Youth Lists helped me, then my whole life is worthwhile.

Would you encourage your fifteen-year-old self to the web today? If yes, what are your words of inspiration and, if no, what are the words of warning?

Oh, of course! One of the things I’ve tried to do through my life is not forget what it felt like to be young. Teenagers are capable of understanding so much more nuance, of taking care of themselves, so much better than we give them credit for. Sure, some teenagers will find misleading stuff and be suckered into making bad choices, but so will their parents or grandparents. The ability to avoid the nightmares of the web is not really age-dependent.

A recent tweet of yours: "EEEEEEE! Websites! Let's build some!" – my brain, 98% of the time.” - what’s the most recent website you wished you could build but didn’t have time to?

A couple of days ago, I found myself wanting a website that would allow me to search recipes by dietary restriction only. All of the ones I found let search by an ingredient and then filter by restrictions, but I was trying to get ideas and had no ingredient in mind.

We’ve created a bunch of new problems on the web today, but they’re worth it, because the world is so much better than it was then.

I would also really, really like someone to invent software to create internet forums that aren’t festering trash-fires of sociopolitics, but that’s a much harder problem.

We’ve created a bunch of new problems on the web today, but they’re worth it, because the world is so much better than it was then. The web is, despite all its problems, a genuine force for good. It’s why I’m a web developer, and why I’ve never wanted to be anything else.

How do you see your next five to ten years? What are you most excited about? Perhaps most afraid of?

I think I will probably still be at npm in five years. We have so much to do! We’ve lucked into becoming critical infrastructure for people who build websites, and as somebody whose mission in life is to make the web bigger and better and more accessible, there’s really nowhere better for me to be. I always want to help today's version of 15 year old me get started. We make life easier for millions of web developers at once, and that’s amazing.

Ten years from now technology will have changed so much there’s no predicting where I’ll be. 10 years ago there was no iPhone; no smartphones at all as we understand the term. That whole revolution happened in less than 10 years. What are we going to invent a month from now that 10 years from now will be ubiquitous and world-changing? I have no idea, but I’m always excited to find out.

Is engineering where you expected to find yourself when you were a kid? If not, what did you think you’d be when you grew up?

I was ambitious, but I wasn’t exactly focused— I just wanted to be challenged, and I considered medicine, law, and engineering because I wanted to be financially successful. When it came time to pick a major, I thought about how much I loved tinkering with my computer at home, and settled on either CS or Computer Engineering [at Carnegie Mellon University]. I never took a programming course in high school, so I wasn’t sure where I’d end up or if I would actually love engineering, but thought I’d figure it out as I went along!

What kind of tinkering were you doing?

I was never one of those kids who wanted to take apart a computer or figure out how it worked, but I’d spend hours playing any game or exploring any program I could get my hands on. I had a stack of 5 ¼ inch floppy disks my parents had acquired through friends and I’d run through all of them. Then, once we got the internet, I started teaching myself how to build websites, monkeying with HTML and building in Dreamweaver.

I had a stack of 5 ¼ inch floppy disks my parents had acquired through friends and I’d run through all of them. 

If you could pick one moment which sparked that initial interest, what would it be?

I went through a rough patch where I questioned whether I’d chosen the right major. I wasn’t feeling inspired, and couldn’t grasp how the assignments would translate to the real world.

This enormous sense of pride that I felt knowing my code had real-world impact was what made me want to make this my career.

But between my junior and senior years, I landed an internship with a company called BodyMedia, a wearable tech company. In one summer I worked on a huge variety of products, from an armband which measured calories burned, to an internal log viewer that helped engineers investigate customer issues. My last project was building a prototype display for a temperature sensor that could monitor a newborn’s temperature in the ICU, and it was something the CEO actually demoed to external partners. I remember the feeling the first time I pinched this sensor between my fingers and saw the display on my screen start to climb. This enormous sense of pride that I felt knowing my code had real-world impact was what made me want to make this my career.

Describe the path that followed, however meandering. How did you get from that to where you are now?

Like many Carnegie Mellon students, I found my first full time job through the school’s career fair. Salesforce was just starting up their university hiring program (engineering was <100 at the time) and I was their first hire through the program. It was a great time to be there, and I got to work closely with very experienced engineers and managers.

I stayed for 7 years, which is unusual in the Bay Area. I switched teams often but in my last year there, I decided to move into management. I was always interested in team dynamics, dependency management, and career development, so this felt like a natural move! My impact could be greater than it would be as an individual contributor.

A year later, I ran into a former manager of mine named Pete Morelli who had gone to Twitter, which got me thinking about working for a consumer company. I felt more comfortable making that drastic change with the help of someone familiar who’d look out for me.

So I ended up at Twitter, running all of the San Francisco teams in the Data Products org. When our external partners connected Twitter with their products and businesses, our tech did that. 

After two years, though, I was craving a change. I found out Pete was leaving for Lyft, and immediately added it to my list! I didn’t necessarily set out to follow him, but I loved my interviews and the team I’d be working with— and that’s where I am now.

Do you see a “typical” journey into the tech industry for the people you hire? Does the continued focus on CS degrees (and insistence that they’re not required) indicate that a bias still exists towards them?

I hire people from all sorts of backgrounds. There’s people with CS degrees from all sorts of programs, there’s bootcamp grads, and self-taught engineers. Some came from startups, others from big name Silicon Valley companies, and some worked in the government or military. They all approach crises and challenges differently, and that’s why we’re such a strong team.

I don’t think it’s wrong to place value on a CS degree; I think it’s very helpful to have several people on my team with a traditional CS background– but I don’t require it, and I make sure it’s not mentioned in any of the job postings I write.

[My team] all approach crises and challenges differently, and that’s why we’re such a strong team.

Do you ever feel pressure to be a mentor, an example, or a role model for other underrepresented folks in tech? 

I would argue that if a leader doesn’t feel a responsibility to mentor or be a role model for underrepresented folks in tech, then they should not be in leadership. It’s not so much a pressure as it is a part of my job. I got to where I am today because people advocated for me and modeled great management. It’s essential that I pay that forward, and do so in a way that benefits groups who are typically marginalized.

I’ve heard you say before that women and minorities should know their worth, but (in the interviewer’s opinion) just as much about others recognizing that worth. How does that problem get addressed?

This is an important point, and I'm always skeptical of putting the onus of responsibility solely on underrepresented people without also addressing the issues of the systems that oppress them. So when I say “know your worth” I mean two things:

Women, people of color, and all marginalized individuals should never feel like we have to stay in a bad situation (a job, a team, or even a relationship) if we have the means and the privilege to leave. We don’t owe anyone our time or presence.

If marginalized individuals do need to stay in a non-ideal situation (like needing money or stability or a big name on our resume), we shouldn’t let those situations influence how we feel about our own self-worth.

In terms of others recognizing and appreciating our worth, the bulk of the responsibility lies with leadership and with majority groups. That’s why I say it’s my duty as a person with power and privilege in my organization to represent the voices of those with less power and privilege. It comes with the job. I advocate for the underrepresented folks in my circle and I encourage my peers to do the same. When opportunities come my way, I’m quick to either share or defer them to those who deserve the spotlight. Every leader with privilege must do the same.

I'm always skeptical of putting the onus of responsibility solely on underrepresented people without also addressing the issues of the systems that oppress them.

Your open letter to teammates struck a chord with me. What prompted it? Did you notice any change as a result?

People know they can come talk to me about anything, whether it’s professional or personal. They will always get real answers from me, and I’m not afraid to be vulnerable and share some of my own hard-fought lessons. However, I wanted all the people I work with (not just those on my immediate team) to know that I care about them, and they all have the same invitation to talk in a forum that I feel is more productive. I don’t ever want my title or my busy calendar or the fact that we don’t work together directly to prevent someone from reaching out to me. Since then I’ve met with several people, and it’s great to have new connections as a result.

I don’t ever want my title or my busy calendar or the fact that we don’t work together directly to prevent someone from reaching out to me.

What was the most fraught thing about making the transition from individual to manager, as a woman in engineering? Any advice? 

Regardless of gender, most people who make the jump to a leadership role struggle with handling the simultaneous increase in responsibility for others while also needing to give up control and delegate. Where this gets interesting with regards to gender is that women are often conditioned to put others before ourselves. That can make it even more difficult to delegate work (especially if it’s not exciting work), or to feel okay letting some important things drop when your workload is overwhelming, or to prioritize time for yourself rather than your team.

women are often conditioned to put others before ourselves. That can make it even more difficult to delegate

All managers should view their role as one of service to their teams. I always want to put them first, but with the help of an executive coach, I began to see how some of my ingrained (and gendered) behaviors weren’t benefiting anyone. I’d forget to delegate or create time in my schedule for my own development in favor of taking care of my team’s day-to-day needs. It’s something I still fight, and it’s the opposite of great leadership.

The leap to management can leave you feeling lonely, and it’s really important to have a diverse support group of mentors and peers. I love this blog post by Lara Hogan about developing your “manager crew.”

If you could do everything all over again, do you think your journey would be the same? Would you want it to be?

There are a ton of different decisions I might make that could have potentially led me down a different path. But I don’t believe those paths would be any better or worse than the path I’ve chosen today.

Is there anything about the internet or technology that you remember from your childhood/early years that makes you feel nostalgic?

The only thing I’m really nostalgic for is privacy. Like many people my age, I’m glad social media was not around during my high school years!

What excites you most about the industry now? What scares you?

When I see people like Arlan Hamilton (founder of Backstage Capital) getting the shine she deserves—and the money that goes along with it!— I get excited and inspired. I can’t yet say that tech is a place where everyone can belong and succeed, but there are pockets you can find that will give you hope and signal that a change is coming. I’m here to be a part of that change too!

data is only as unbiased as the people who are querying it

What scares me is the frequent assumption that data is objective and unbiased, especially as companies rely more and more on data to make decisions. But data is only as unbiased as the people who are querying it. The way we act on this data can have a real effect on our communities, so it’s really important that we feel some type of personal responsibility for what we’re building. A diverse team can help each other recognize their blind spots and ensure they’re using this data responsibly.  

Is this where you expected to find yourself when you were a kid? If not, where did you think you’d be?

As a kid, I always thought I’d be an actor. I acted commercially a little bit between ages 6–12, but stopped once I hit middle school. Coolest achievement: being in a commercial with James Earl Jones (I’m at 17-19s)!

After that I’m not sure I really had any expectations. I’ve always been an “art kid,” so I also had that as a vague career aspiration. I thought I might return to acting, but mostly I just hoped for a career that made good money. My mom worked a couple jobs when I was growing up just to pay the bills and it put a lot of stress on our family. I wanted to make sure that as an adult, I wouldn’t have to struggle like she did.

What was your ‘eureka'  moment—the one that, if you look back on it now, sparked your interest in design?

My older brother started learning web and software development when he was younger, and passed on that passion down to me. I started making ReBoot and Sailor Moon fan sites and personal websites in elementary school, and kept with it. I loved playing around with image-rich HTML layouts, writing my code directly in Angelfire’s browser-based text editor, before the days of Dreamweaver or Frontsite.

I started making ReBoot and Sailor Moon fan sites and personal websites in elementary school, and kept with it.

I went to college at Smith, planning to major in East Asian Studies. But I took a Government class on a whim, loved it, and that became my major — with an arts and technology minor. My financial aid took a long time to settle, so by the time I was finally able to pick a work study job, my options were pretty limited. A dance professor needed an assistant, which included some light graphic design and web work, so I jumped on that right away. I was a terrible assistant (sorry Robin), but I think I did pretty well with the design work. That was the first time I really thought, “hey, I could do this as a career. Someone has to make websites for people.” I started focusing more on developing my design skills after that.

Describe your career path, either from or around that moment. What events, random or connected, brought you to Automattic?

Strap in, because it’s kind of a windy ride!

After my first year work-study, I felt pretty stoked about design and technology, and started working at the computer labs. My college’s ETS (“Educational Technology Services”) staff empowered and encouraged me to learn more about any tech I could get my hands on: audio and video editing, graphic and web design, testing different software for use in classrooms, setting up hardware, etc.

Some time during my junior year in 2008, I saw a posting for an internship at a local web design agency, and was luckily selected! That became a job, which connected me to another contract web design job in the area, and that trend of finding and working with local agencies as a contract designer lasted for a couple years. Eventually I found a full-time job, which I lasted at for a little under a year before — gulp — getting fired. It was a pretty humbling moment. I tried to find another local gig, but there just weren’t a lot of design jobs. My partner and I moved out to Boston; there, I found a startup design job, but it became obvious that the startup wasn’t going anywhere, and neither was my career. I felt like I’d hit a wall that I didn’t know how to get over.

Eventually I found a full-time job, which I lasted at for a little under a year before — gulp — getting fired. It was a pretty humbling moment.

That’s when I heard about a local apprenticeship program run by Fresh Tilled Soil. It was a three month program where I’d be paid to work alongside experienced designers. I had to get in. I worked super hard on my application, and was ecstatic when I was picked. The experience was transformative for me. I was paired with Steve Hickey, an experienced mentor who worked with me to figure out where I was really struggling and, together, we were able to design a curriculum to help me overcome these blocks. I also worked with fellow apprentices on some pretty complex and challenging client projects. It was an amazing experience.

Towards the end of my apprenticeship, it was time for me to start looking for a full-time job. At some of my early contract jobs, we’d used WordPress, which I’d begun to like more and more as I built up my skills with it. One of my jobs took us all to WordCamp NYC, and it was there that I was introduced to how welcoming and interesting the community was, and that inspired me to start getting involved.

So between the whirlwind of my various contract jobs, my ill-fated full-time job, my startup stint, and my apprenticeship, I was contributing to the design of WordPress. I met and worked with designers from Automattic who I really admired, and put Automattic on my map as my “dream job.”

So after the apprenticeship, I finally felt like I had the skills and confidence to apply at Automattic — so I did. I got an interview, did a trial project, was hired, much to my delight! It’s been great!

I met and worked with designers from Automattic who I really admired, and put Automattic on my map as my “dream job.”

You’re very much involved in design and inclusion efforts— the Design & Exclusion remote conference, for example. What sparked that involvement?

The Design & Exclusion conference was an Automattic endeavour spearheaded by our Head of Design & Inclusion, John Maeda, along with my colleague Ashleigh Axios (in partnership with the MIT Center for Civic Media and The Mashup Americans). There was an internal call for support, and I was happy to hop onboard.

I want to continue to do all I can to make informed, inclusive decisions, and make the web a safer and more open place for marginalized folks.

As a queer woman in tech, I think a lot about inclusion and exclusion, and how my design decisions impact how people feel included or excluded from our products. I had the privilege of seeing Mike Monteiro’s “How Designers Destroyed the World” at An Event Apart a couple years ago and it’s really stuck with me, and the feeling of responsibility for the work I put out into the world just keeps getting reinforced the longer I’m in tech. I recently read Technically Wrong by Sara Wachter-Boettcher and continue to be amazed (but not surprised) by how much damage we as designers and tech workers can cause. I want to continue to do all I can to make informed, inclusive decisions, and make the web a safer and more open place for marginalized folks.

As a designer, what’s the most important piece of advice you’d give an underrepresented minority entering the industry now?

Okay, some real talk: I’m queer and pretty butch, and my communication style can be pretty aggressive at times. This has awarded me a ton of privilege that my more feminine colleagues have not experienced. It also makes it pretty easy for me to slip into some toxic masculinity of my own (‘sup patriarchy). If this sounds like you, then you’ve got to learn to actively check yourself. Don’t let yourself be “one of the guys” in a way that diminishes, disrespects, or objectifies your female colleagues.

I’m queer and pretty butch, and...this has awarded me a ton of privilege that my more feminine colleagues have not experienced.

Probably the biggest advice I’d give is to show up, and keep showing up. Make your face known. Take on responsibility when it’s offered, and then make sure to follow through. If you’re going to be late with something, communicate that early. Most deadlines can be moved with enough prior notice! Lastly, learn how to say no.

Do you ever feel pressure to be a mentor, an example, or a role model for other underrepresented folks in tech?

I’ve felt internal pressure to mentor new folks, but I don’t often seek out the opportunities to on my own. I think I do better with structured events, like the recent speed networking I attended for Tech Job Tours. I like helping younger or newer designers make connections to further their learning and careers, but I feel like long-term, one-on-one mentoring isn’t the right role for me. Luckily, I haven’t had any external pressure to do this, though I see it happen to other underrepresented people in tech.

If you could do everything all over again, do you think your journey would be the same? Would you want it to be?

I would have taken some film or animation classes in college. Seriously. That stuff’s hard to learn on my own. But that’s probably it, though. Even the bad stuff, like getting fired and struggling with my career progression, was important to experience.

Is there anything about the internet or technology that you remember from your childhood/early years that makes you feel nostalgic?

Definitely fan sites, webrings, forums, and chatroom roleplaying. I spent so much time as a kid working on my ReBoot fansite and chatting with fellow fans on alt.tv.reboot, searching through Sailor Moon webrings for new sites, chatting with fellow nerds on a videogame forum, and roleplaying on AOL (Rhydin 4 life). “Social” looked a lot different in those days! I miss it.

How do you see your next five to ten years? What are you most excited about? Perhaps most afraid of?

I’m afraid of the current state of global and US politics, and rapidly escalating climate change, so this is a hard one for me. All I hope is that my partner and I are alive, healthy, and safe in that timeframe and beyond. That’s what matters to me most.

You’re very inclusion-focused in your work; is this always the case for tech evangelists?

I'm probably one of the most engaged in doing diversity and inclusivity work within the Microsoft Dev-Rel community, but there's a lot of others on my team doing that work: Suz Hinton and Rachel White, for example.

Do you wish people would do more of that?

Always! But Microsoft’s actually pretty good about it, at least as far as a large tech company goes, and part of that is historical. Microsoft rose to prominence in the 90s and was known for being very aggressive; I've certainly heard internal stories of what it was like then, but things changed. Microsoft shut down in a bunch of markets and was humbled. In trying to reinvent itself (technically and otherwise), they had to change the culture within. That cutthroat attitude served it's place in the 90s— that’s not to say that it was a good thing. It was one way back then, but it doesn't work now.

I think our current CEO has done a really good job of understanding what Microsoft needs to be both as a business and as a culture. Just in the past four years, there's been a huge amount of culture change. Diversity is talked about so much more now, and we are more focused on it— still a long ways to go, of course!

What's your favourite thing about being a technical evangelist? And don't say "the people"!

I love being able to travel and engage with folks in the broader development community in a much more personal way. Going to conferences and actually meeting everyone, talking to people, getting their stories, and understanding what their lives are like, as developers and as people.

Is this where you expected to find yourself, growing up in Texas?

Hah! Definitely not, at all. I had a bunch of childhood dreams— I wanted to be a pilot for a long time because I loved planes. Both of my parents were middle school teachers, so that wouldn't have been impossible either. I also considered technical theatre, because I had a performing arts background and had been doing it for a long time. Computer science emerged as an option in high school. I was starting to look at colleges in both computer science and electrical engineering, because physics was fun, and I liked my teacher.

Growing up, we didn't have much money. There were definitely times where we struggled financially. I think that's something that many people in tech can't relate to, and it's interesting to see how that influences their decision-making. "Starving artist" isn't romantic; I haven't been one, but I lived without much money when I was younger. It's not a romantic life. It's just hard. As much as I respect my parents for their careers, I wanted something stable. When it came to theatre I thought, "I have the talent, and I have enough privilege to make it work," but I didn't want the struggle that I knew would come with it. I think I could have made a life out of that, but for stability reasons, I didn't.

These decisions are practical; electrical engineering was my best chance of finding a good job. Then, when I was looking at colleges in fall of 2000, it was just after the dotcom burst. So I was like, "I like coding, but is computer science going to be an industry in five years? Probably not. I won't do that."

Do you have a “eureka” moment? A single moment where you knew tech was where you wanted to be? 

I don't think I had one moment. My parents say the same thing— they just knew I would make a good engineer. As a kid, I would play with Legos: I’d build the toy once with the instructions, and then I'd throw it out and make my own thing.

My parents tell a story of when I was 4 or 5, and they got me a Lego set for Christmas. I was sleeping, my mom was taking care of my sister (who had bronchitis at the time), and my dad was setting up the Christmas stuff. He built the Lego set and set it up for me, and it took him four hours to do it. In the morning, the first thing I did was take it apart and build it myself— in twenty minutes. So I've always had that knack for taking things apart and putting them back together.

[My dad] set [a Lego set] up for me, and it took him four hours to do it. In the morning, the first thing I did was take it apart and build it myself— in twenty minutes

After college what happened?

I knew I wanted a graduate degree, but I didn't know what to focus on. I was chatting with a professor during my senior year and I had no idea what I wanted to do. He told me to just do a Phd, and I was like, "OK, fuck it." So it was kind of a flippant decision! I was just like, "Sure, I'll do it."

By the time I finished it, though, I had realised that the academic world wasn't for me. Most of your time isn't actually spent teaching. It's more like 10% teaching, 20% with graduate students, 10% on research, and the rest is writing grants and politicking, trying to get money.

So I started looking for a job!

I knew I wanted to be in SF, or at least the bay area. My partner and I moved out here around 2010, after the 2008 recession, so jobs were a bit scarce. After several months of nothing, I got two offers at once: one with Intel, the other with this tiny startup called Particle Code. They were working on this cross-mobile-platform for 2D games. Think Unity but for 2D isomorphic games on mobile phones— think Blackberry and Nokia! I thought, "Well, I know Java, and this is kind of like embedded programming, and you'll pay me? OK!" and I took it because I just needed a job at that point.

He told me to just do a Phd, and I was like, "OK, fuck it."

What was that job like?

That was a great startup— a surprisingly good team with a good culture, something I didn't understand until later when I actually had something to compare it to. The founders were from Israel, and our CEO was a woman and that was awesome! My teammate was my polar opposite: I have a Ph.D and lots of formal training, and he had none whatsoever. He'd taught himself to code in the Israeli special forces; in between doing...various military things...he'd read programming books. We made a great team, but we were so different. That taught me an early lesson: your background doesn't predict your success nearly as much as people think. It taught me the value of different backgrounds and perspectives.

Where’d you go next?

I worked for the startup that acquired us, and got to do some really cool technical work, but there were cultural issues. That's one of the two times that I've left a job in the tech industry.

your background doesn't predict your success nearly as much as people think.

After that, I went to Rdio, and it was the complete opposite. Really good culture, which is what I was looking for first and foremost. We all cared deeply about music, and the product reflected that. I became a technical lead there and helped build the team, and ended up doing leadership and mentorship as well.

Then, when Rdio was acquired, I briefly worked for Pandora. I left and was torn over it! There were a lot of great things, and I was really impressed by their diversity. When me and one of my teammates— both of us queer— arrived there, we were like "There's queer people everywhere, this is amazing!" The people side was spot on. But from the technical side, they were struggling. So, shortly thereafter I went to Microsoft.

Nice! You’re super involved in Node as well— how did that start, and how did the recent events affect you?

That all started in 2013 with JSConfUS. It was there I learned about Nodebots, got involved in Johnny Five, and started speaking at conferences. Through Johnny Five, I got to work with the Node project directly. Then, at NodeConf Adventure in 2015, there was some discussion around culture, diversity and inclusivity in the Node Project. I was passionate about it, so we ended up forming the Inclusivity Working Group there, because there were enough of us who felt there were problems to be solved. I was just in the right place at the right time. That evolved a lot over the years. There was a lot of pushback— some successes, a lot of failure.

"Leadership" is a hybrid of middleman, manager and community voice. Whenever things go wrong, I was the one who had to deal with it, and it could never wait.

The group folded for a variety of reasons, a little over a year ago. We followed that up by creating the Community Committee, which was structured to avoid some issues the Inclusivity Working Group had, and that's going through some turmoil right now. Emotionally, it's really hard to do that stuff. "Leadership" is a hybrid of middleman, manager and community voice. Whenever things go wrong, I was the one who had to deal with it, and it could never wait. It took me away from conferences and people, and that's how it goes.

You’ve taken a break from that now, which makes sense. Do you feel pressure to be a mentor/role model for other queer folks in tech?

It depends on context. I'm constantly re-evaluating how much I want to "flag". A lot of my appearance is based on that duality, and I modify my language to intentionally inject ambiguity. My partner is "my partner". I'm super-careful to not reveal gender right away. I'm not afraid of people knowing. I want that ambiguity. I want people to be confused at first. Especially being bi— as soon as gender is revealed, it's "oh, you're straight! Oh, you're gay!" I think it's a small thing I do to combat that.

I definitely feel the urge to be a role model as well, especially when I'm privileged enough in terms of income and stability. White male privilege is also very much a thing for me, so I try to be as out and outspoken as I can be. With my writing, I try my best to give encouragement to other queer folks.

Growing up, did you have any queer role models in the field? Did you look for them?

That was a very long and slow process for me, and part of it comes from being bi. I was in high school in 90s Texas. Matthew Shepard happened when I was in high school. My brain early on thought, "well, I'm interested in women...." and I just didn't finish the rest of the sentence. Discovering my queer identity took a long time— I didn't embrace it until I was around 30, I think.

I definitely feel the urge to be a role model as well, especially when I'm privileged enough in terms of income and stability.

It's interesting to see how my view of myself has changed over the years. I'm really happy in my mid-30s now. Back then, there were very few gay role models, and I can't remember anyone who was famous or well-known who was bi. Will & Grace was brand new and controversial, and it played to some of its own stereotypes. So, I mostly just forged onwards and figured it out myself. That's always what I've done. I don't think it's something I have to do anymore, but when I was younger, I didn't have much choice. That's just the way I learned to navigate the world.

And now, a few rapid-fires to wrap up: first, what are you nostalgic for from those early days in tech, if anything?

The sense of wonder! There's this cool thing now and we're just on the cusp of something that's really great and it's going to revolutionize the world! We've got email now, we can communicate around the world instantly! The rise of AOL IM was like "oh my gosh, this is instant!" It was bypassing the phone companies, it was deregulated. It's ironic that those ideas were very much socialist, overthrowing-the-establishment kind of feel. That feeling of possibility, I miss.

It's ironic that those ideas were very much socialist, overthrowing-the-establishment kind of feel. That feeling of possibility, I miss.

How do you see your next five to ten years?

I don't have a great answer for that! I switched from dev to evangelism earlier this year, so I actually have a lot of questions around what I'll be doing. I know that I definitely want to continue my inclusivity work, but I don't know what that's going to look like.

Are you looking forward to it?

Yes. I'm not afraid of it. One thing I've learned is that things do get better. They do work out as long as I keep trying. There's some nuance to that, of course. There can be a lot of painful moments, but if we like who we are now (and hopefully we do, or do as we get older), then we shouldn't view those things completely in the negative. We don't have to necessarily forgive anything, but I think it's important to not harbour resentment. That’s very easy for me to say, because it comes from harboring resentment and processing my past. But overcoming that gives me confidence that I'll be able to overcome any adversity in the future.

If you could do everything all over again, would it be the same? Would you want it to be?

I would probably do it the same, which is weird to think! I would do all these things that I know I'd hate, but I think they're an important part of how I got to where I am now. And where I am now is exactly where I want to be.

Is this what you expected to be doing when you were a kid? 

Absolutely not! I wavered between graphic design and architecture. I didn’t have an understanding of either of these professions, but I always liked painting and drawing, and as a kid, I sketched these super-detailed, fantasy-cave-like homes with cool features like swings and slides instead of stairs. But I also liked math and history and art and reading, and had a lot of conflicting ideas of what I’d do towards the end of my time in school. I half-heartedly started to create a portfolio to apply for a design program, but eventually ended up studying something quite different.

What was that?

I had lost confidence in the design/architecture idea. Writing and reading had become more important to me. I enrolled for a major in Communication Science, with Art History and German Language and Literature as minors. I pretty much picked what sounded most fascinating and most relevant to my skills, without knowing where it would lead me. I fell in love with it.

That’s definitely not front-end development. If you think back, which single moment made you fall in love with tech? 

I remember that quite clearly. Between my last year in school and starting university, I had a few idle weeks. I'd just gotten my first own computer, a heavy noisy notebook that came with an AOL CD, promising internet access. I figured out how to set up this internet thing and get unlimited access to forums and ICQ and Napster and the WWW.

Then, a friend came over one afternoon and proudly mentioned that he was building a website, which fascinated me. Until then, websites were pretty magical things built by...  super-professional grownups, maybe? With special equipment, in large offices? Definitely not by people like my friend, or me. I didn't quite believe him, so he opened up a text editor on my computer, typed a few words, saved the document as index.html, and then opened it up in a browser. I couldn't believe that he just put something on the internet, just like that! We then started to mess around with the page, adding some markup, followed by colors.

Until then, websites were pretty magical things built by...  super-professional grownups, maybe?

I was completely hooked. I always loved to create and write and style things, and this new super-fascinating outlet came with the prospect of feedback, communication— connection. But it didn’t occur to me yet that this “something with computers” I enjoyed was a career option, so I continued with my studies.

What path did your career take after that?

After graduation, I landed a trainee position as PR person for a large contemporary art exhibition. I loved working with artists and curators, but I found myself helping often with small print design tasks or website maintenance. I was working with the designers and the "IT Team" quite a lot.

Unfortunately, though, I also got to know the art world's long work hours, miserable salaries, rough competitiveness, and nepotism. A change was needed.

During my student years, I’d earned some money working as "webmaster" for my institute, building tiny websites for small businesses or designing flyers for local clubs. I missed the freedom and joy of just building and designing little projects and being my own boss. So I decided to give myself one year to build a freelance web design business.

My first large client job was in Berlin for an artist that one of my previous colleagues now was working for, Berlin was where I wanted to be anyway, so I moved there. And after a year, I wasn’t broke! I started working from coworking spaces – that just started being a thing in Berlin back then – where I met people who would refer me to new clients. One project followed the other, and soon I had gathered a solid client base, and was busy networking and learning and growing my tiny business in Berlin. I also started to do remote work for some clients on the US west coast, and one of them made me an offer to work full-time for them in San Francisco.

I was very hesitant to leave the life and work that I had just built in Berlin, but I agreed, because I was also super-curious to see what living and working in SF is actually like. I thought I’d only be there a few months, but I ended up staying almost four years.

That’s a huge step! How did you settle in?

The first few weeks were packed with paperwork, finding a place to stay, figuring out the commute, meeting new people, working long hours in the office – so I didn’t have much time to get homesick. What took me a while to be comfortable in were the little interactions and social rules: I had to get the hang of ordering a burrito without holding up the line forever. I had to accept that people start to eat before everyone’s order has arrived, and without saying “Guten Appetit”. I learned that double-dipping is a thing. Being comfortable in the language and not feeling awkward when ordering a coffee or buying a bus ticket took me while.

Living and working in the Bay Area taught me a lot about my work and the tech industry, and how it compares in the two cultures. The pace is so different: In Germany, I was used to working efficiently, spending as little time in the office as possible. Social life happens after work, not during. In San Francisco, I often arrived in the office when it was still dark outside and left late at night. I felt a much stronger (though subtle) pressure to make work your life, to socialize with colleagues and their families. Taking vacation other than a few extra days around the holidays was unusual. Even after big life events like becoming a parent or getting married people would be back at their desk the next day.

I was used to working efficiently, spending as little time in the office as possible. Social life happens after work, not during. In San Francisco, I often arrived in the office when it was still dark outside and left late at night.

After four years, I decided to return to Berlin. I did fall in love with California, though, and haven’t been able to feel 100% at home again in Berlin since. Being abroad definitely built up my ability to get along anywhere; I’m still escaping regularly and trying to find jobs that allow for travel. San Francisco also taught me that Berlin is the city where I can make the most meaningful contribution, where my network and the local community are really cool and unique and I can make an impact by organising cool stuff, and balance them in a way that feels good.

You organise a number of events. How'd you get started doing that?

Before going abroad, I worked mostly with Ruby and PHP developers, who all had places where they hung out, exchanged ideas, made friends and found jobs and clients.

I really really wanted a place like that for myself, to meet other designer/frontend developers like me. But back then (ca. 2010) there was no meetup like that in Berlin. So I started upfront.ug, a monthly talk evening in Berlin for designers and frontend devs. It's now been running for seven years, and we’ve put it on more than 75 times.

I was also involved with Open Tech School and started volunteering with JSConf EU. The tech community in Berlin is very active and has a strong ethos of DIY, free education, and mutual support. I got involved left and right, learned a lot about volunteering, team work, how to find venues, sponsors … and loved it.

San Francisco put that on hold for a while, but also introduced me to Nicole Sullivan. She was one of the first women I saw giving a talk at a tech conference, and her writing and speaking about frontend development topics had motivated and encouraged me for years! She also came up with the first conference about nothing but CSS: CSSconf US. This was novel at the time; there’s many CSS-focused events now, but just a few years ago people were actually wondering how one could talk an entire day about CSS. We became friends, and over some drinks, she asked me if I wanted to bring CSSconf to Europe. Of course I did! And from all the years helping with JSconf EU and other events in Berlin, I had the network and support to make that happen.

This was novel at the time; there’s many CSS-focused events now, but just a few years ago people were actually wondering how one could talk an entire day about CSS.

The very first CSSconf EU was the hardest and scariest thing I’ve organized, but seeing all these people come together made it worthwhile. We’ve run it four times now, and it still feels new.

Do you ever feel pressure to be a mentor or a role model for the underrepresented in tech?

Any opportunity to directly mentor or sponsor someone is actually really rewarding, and doesn’t feel like work or something that I’m pressed to do. Ongoing volunteer work is different: organizing events, workshops, and conferences can get overwhelming. Over the past few years I’ve become very conscious knowing when I need to step back and take care of myself.

That isn’t always possible, though, and that’s where I feel pressure. I can’t easily drop out of organizing a conference once it’s rolling, or look away if an attendee or volunteer needs help. I can’t stop caring when something goes against my values and goals. If I want meetups that don’t feature white male speakers only, or a safe learning group, or get rid of offensive language at my workplace, I have to fix it myself.

People from underrepresented groups are expected to fix issues of diversity and inequality, and I think that’s unfair and is a problem.

Behind the scenes, it’s usually the people from underrepresented groups who speak up, build cases and fight for more inclusivity, and then put in the work to implement it. They educate and lobby, publicise, network, and suffer the abuse, but don’t get credit for that hard work.

People from underrepresented groups are expected to fix issues of diversity and inequality, and I think that’s unfair and is a problem. Our community needs to figure out ways to share that work more fairly, and recognize and reward the work that is done by people from marginalized groups.

If you could do everything all over again, do you think your journey would be the same? Would you want it to be? What would you change?

I hope it would be the same! I can’t say I regret anything. I'm grateful for the various fields and work situations and cultures I got to experience and think it’s exactly what makes me fit to do my current job and community work. The only thing I wish I had access to earlier is a mentor, someone to ask for help and advice when I need it. This is especially true when it came to negotiating and leaving unhealthy work relationships; I wish I’d had a more experienced mentor tell me to be tougher and less naive.

I'm grateful for the various fields and work situations and cultures I got to experience and think it’s exactly what makes me fit to do my current job and community work. 

Is there anything about the internet or technology that you remember from your childhood/early years that makes you feel nostalgic?

Oh yeah– Napster. Before it, I used to wait in front of the radio, cassette ready, with the finger on the record button, waiting for a favorite song to come on. I saved my allowance to buy a record or CD, and would listen over and over to the thirteen or so songs on it. I learned the lyrics by heart, translated them word by word, and gathered every bit of information from MTV about my favorite artists.

Napster changed that, but was similarly fascinating, because you still had to wait half a day for one song to download. Obviously, the way I consume music has completely changed since and I definitely don’t want to go back to cassettes! But when I remember CDs and cassettes and loving music so much and investing many hours to craft precious little mixtapes for friends— I feel nostalgic about that.

How do you see the next five to ten years? What are you most excited about, or most afraid of?

I’m more and more interested in making people work together well in teams, and I'm trying to find projects where I can work on building and growing teams – but also stay involved in code and design and shaping the product.

I give workshops more often, and have been a guest lecturer at the University of Applied Science in Salzburg for a while now. They have a MBA programme for web development – one of the first in Europe, organized by Brigitte Jellinek. She approached me to teach a CSS deep-dive class, which is challenging but very rewarding. So that’s another direction I want to pursue. Managing teams and teaching students is fun and fascinating when it works, but not really within my comfort zone yet, which is sitting in front of the computer, happily coding along by myself.

I'm still learning a lot about dealing with responsibility for more than just myself, how to work with teams and stand in front of a class room. So I hope to be much better and more comfortable with that in five or ten years.

How do you balance your job with writing and advocacy? How do you set aside time to write?

One of the key traits of a great Product Manager, in my opinion, is the ability to make tough trade-off decisions and prioritise ruthlessly. When you have two or three competing features that you want to develop, it can be a hard decision, but having a simple decision-making framework makes it a little easier.

So, before and after work, and during lunchtimes, I prioritise the advisory and content work I do. For example, I often have morning meetings bright and early with prospective investors. I then write during my lunchtimes and weekends. Finally, I meet entrepreneurs either at lunch or (on the rare occasion) after work.

I’m less willing to sacrifice time after work because I have a young daughter and beautiful partner with whom I prefer to spend as much time as possible. They mean the world to me and the least I can do is put them first as much as possible.

Is this where you expected to find yourself when you were a kid? If not, where did you think you’d be?

Great question. Honestly, the answer is no. My beginnings in Tottenham, North London, were humble: my dad was a cab driver whilst my mother worked at a Nursery. In my youth, I was fascinated by tech but never had any relative role models I could speak to about it. I remember how excited my brothers and I were when we first logged onto the internet at a local technology park and played games on Nintendo emulators over the internet.

I always fed my curiously as a kid and sought out opportunities to understand what I excel at and enjoy. I was always passionate about playing football (soccer) and some would say I was quite gifted at it too, but I never enjoyed playing or training when the weather was cold. That is when I realised that life isn’t as simple as just doing what you are passionate about for the rest of your life.

In university, I discovered a passion I was skilled at. I studied Business Management but I excelled at modules related to entrepreneurship, and honed in on business skills. For example, my friends, my elder brother and I recognised that our niche music taste (UK Grime and Hip Hop) was so fragmented online, so we created Mixtape Madness to scratch our own itch. It was an online platform that allows music lovers to discover and stream UK Urban music. We grew the platform and all its digital properties to over 250,000 users, with over half a billion streams to date. However, I decided to stop as I felt like I needed to succeed at managing products for other startups.

Working on a placement at an interdealer brokerage called ICAP when I was 19 opened my eyes, too, as nearly everyone I worked with shared stories of foreign adventure from their holidays and trips abroad. Until then I had only travelled to my country of origin, Ghana. Almost on gut instinct, I booked a three month ticket to South America. A single ticket into Peru and a single ticket out from Chile, and nothing in between. I ended up travelling alone and having amazing experiences with truly special people along the way.

What was your ‘eureka'  moment—the one that, if you look back on it now, sparked your journey into the industry?

Mixtape Madness was born in 2011 when I was twenty-three years old. I didn’t realise it at the time but I was experiencing exactly what it means to be a Product Manager and a founder. I was scratching my own itch, feeding my curiosity and speaking to customers early and often to iterate on products. I just didn’t know at the time that Product Management was a thing.

Looking back now, I began to realize how I could operate at the intersection of my passion, my expertise and where there was a market need for my product.

…and then, from that moment, what path did your career take? 

As I mentioned, my time at ICAP led me to go backpacking across South America. At ICAP, my friend Denis and I were both at placement at city firms in London. We both went to Brunel University and started our first business Saffirm together. Our aspirations grew beyond the confines of our placement opportunities. Although we both felt like we were learning a lot, we were not passionate about careers in Accounting and, in Denis’ case, Operations.

We joined the Multicultural Interbank Network run by a guy called Frank Makan, which brought together Black and Minority Ethnics that worked at the top 10 investment banks and accounting firms in the city. It was incredible to see role models that looked like us and had journeys we could relate to. There were nothing-to-something stories from working-class folk born in underrepresented communities, striving through the educational system to adapt and excel at city-based careers.

It was incredible to see role models that looked like us and had journeys we could relate to.

The events touched on a range of topics, such as Investing In Africa or Celebrating the Inauguration of Obama. I developed the foundations of my network and connected with a mentor who worked as a deal originator within private equity. With him, I went for the first time ever to a private members club as he got me to think deeply about my career choices. In the end, I decided that being a management consultant allowed me to be a problem solver, remain entrepreneurial and learn how businesses work. My mentor put me in touch with current and ex-Ernst & Young staff, and I was so proud when I received an offer to their Graduate Advisory Scheme. I remember falling to my knees and thanking God as I saw the smile on my proud father’s face.

I left Ernst & Young because I felt I couldn’t be my true self within the workplace. I wanted a smaller environment where I could make more impact. I went camping across East Africa for a month with my brother and friend Cel, then went to work for a consultancy startup called Elixirr. That was an amazing two years working on projects in South Africa, Uganda, Namibia and Kenya among others.

My fondest experience was eight months spent in Silicon Valley and San Francisco building my network of VC’s and startups and connecting relevant startups to corporates across the UK and Africa. This introduced me to product management, and I knew I needed to transition into this role within a startup. Consulting had allowed me to work and travel to over 40 countries in 5 years which was incredible, but I was ready for a change.

Blogging began two years ago as an expression of my creativity and an opportunity to share my evolving point of view. I remember originally starting to blog because this created an outlet for me to be free, creative and to speak my mind without restraint. I could be 100% my authentic self when I wrote. As I began to build an audience, I began to connect the dots and saw patterns emerging around startups, investors and culture. These were the key themes I spoke most about. I knew I found the core of my niche when I heard that “1% of VC backed startups are black-owned”. From then, I knew I could impact that directly and nurture more successful founders (future role models) from backgrounds like mine.

I could be 100% my authentic self when I wrote.

I doubled down on my niche: Diversity in Tech. However, I felt less excited about engaging with big business who weren’t willing to be transparent on metrics related to diversity or show representation on their board. I remember speaking at events such as Diversity in Tech this summer in London. At least 4 companies reached out to me following the event. They all wanted me to speak at a diversity related event filled with junior or mid-management staff. These same companies have the choice whether or not to promote diverse talent to the C-Suite or hire more diverse leaders— but they don’t.

However, I found an opportunity to address a matter close to my heart: that less than 5% of VC backed startups are minority-led. Through my content and advice as a trusted contributor to a number of startup communities, I have built up a network of female and minority-led startups.

From the content I was writing, founders and investors were reaching out to me across Twitter, Linkedin, Medium and email. Founders wanted feedback and advice on their startups, whilst investors were interested in the content I was sharing about deal flow from diverse founders. At the start, I was simply amplifying role models and stories (such as Chamillionaire, Troy Carter and Arlan Hamilton) to an audience eager to tune in. These were inspirational stories that were not widely known by many. Now, I typically help the startups become investment ready and perfect their pitch deck before making introductions where possible to angel or seed stage VC’s.

One of the biggest challenges for an entrepreneur is accessing funding at the start of their journey. More recently, I have been connecting early-stage investors to female and minority-led startups as shown on my website. I send a quarterly newsletter to these early stage investors in the US and UK with a brief description of the startups raising capital. Then I facilitate a match making process for investors interested in particular startups.

Do you feel pressure to be a mentor, a representative, advocate, and role model for other underrepresented folks in tech?

I feel a positive pressure to fly the flag for the underdog, but I also see a huge opportunity to give capital to the underrepresented to get their ideas off the ground.

I find our voice is often not heard especially in modern media, and that’s why I feel it is my duty to amplify those voices.

I am unapologetic about focusing on my niche and sharing my transparency and honesty on a consistent basis. I use the word ‘unapologetic’ purposely; in the US there is a culture of being ‘black and proud.’ We see the culture transcend sports and music to business and politics, with the success stories of Dr.Dre, Jimmy Iovine, and Barack Obama. The UK is traditionally much more reserved and conservative with our culture. As an even greater minority, I find our voice is often not heard especially in modern media, and that’s why I feel it is my duty to amplify those voices. Most people contact me based on the content I have published online, which is great: I’m building a brand that represents me and where I plan to go.

What prompted the idea of the “mirrortocracy”? 

It was inspired first by Kara Swisher, who referenced it during a conversation with Tristan Walker (I believe), but it resonated with me so well. It articulates exactly what I have experienced previously with hiring managers at work.

The track record of hiring and retaining the underrepresented isn’t great. Why do you think it’s been so difficult for tech to focus on “the ‘I’ in D&I”?

Two things need to change: 

First, Founders and Board Members must be a diverse representation of the workers and customers they serve. They aren’t right now. The challenge here is that white middle-class executives are not likely to fire themselves. This is why I work with newly founded startups to help them build a representative board and team from the start. That is the real opportunity to mould companies before the ripple effect starts. I published an article on my blog titled, The First 10 that talks in more depth on this. It is easier to mould clay upfront when it is wet, rather than chip away at it when it sets

Second, we have to stop just measuring money: shareholder value needs to not be tied only to profit and revenue growth, but to humanity, with values and diversity at the core of what we measure. Business cases are traditional tools, existing to justify investment. It’s sad to see Diversity relegated to a CSR initiative, when truly it should be ethically ingrained in the way we live, let alone do business.

we have to stop just measuring money: shareholder value needs to not be tied only to profit and revenue growth, but to humanity

A great example is Toms shoes, who give away one pair of shoes for every purpose: profitable and socially responsible. These days, new VC models such as Indie VC shift the focus to profit and sustainability over growth and entrepreneurs running towards an exit. It’s more difficult, but it can be done. We need to strive for newer,  more meaningful ways of doing business, where we create true win-win opportunities.

Finally: if you could do everything all over again, do you think your journey would be the same? Would you want it to be?

Travelling really exposed me to diversity of thought. I would totally start travelling from a younger age. I would also appreciate and cherish moments with my dad as he sadly passed away 4 years ago.

Is there anything about the internet or technology that you remember from your childhood/early years that makes you feel nostalgic?

I probably shouldn’t be telling this story openly but when I was 14, my brothers and I used to sneak into a technopark local to us with a few friends and use their computers to play classic games like Street Fighter on SNES emulators. It was an early exposure to the power of the internet, but also the disruptive threat it holds; I was fourteen and I found it easy to find these illegal games to play online. At the same time, I thought platforms like Napster and Bearshare would be the end of both the music and movie industry.

How do you see your next five to ten years? What are you most excited about? Most afraid of?

My long game is pretty simple, and I’ve been transparent about it: to continue to gain experience as a Product Manager scaling products at high growth startups, so that in ten years I can join an investment team (i.e. VC) and provide value through my expertise to their portfolio of startups. I want to focus on helping female and minority-led startups grow and succeed. That’s my niche!

What’s your favourite thing about your day-to-day? Least favourite?

Collaborating with other team members. I enjoy listening to the different perspectives others bring to the conversation. Over the years, I’ve found that the best solutions are the ones that include many diverse voices and experiences; I’ve worked with some incredibly smart and talented folks (and companies like YouTube, Honor, and eero) to create transformative technology for others and get exposure to a broad range of design problems across broad market sets.

My least favorite thing? I’ll never get used to being the only (Black) woman in the meetings and rooms of an industry led predominantly by white men. Like many women of color, I often struggle to deal with subtle sexist or racist remarks that transpire in these spaces. It’s a challenge— but then again, my entire existence has prepared me to deal with these aspects.

I’ll never get used to being the only (Black) woman in the meetings and rooms of an industry led predominantly by white men.

What was your ‘eureka'  moment—the one that, if you look back on it now, sparked your journey into technology from behavioural neuroscience?

I’ve always enjoyed creating things with my hands. As a kid, I loved school projects that required a visual aid, like dioramas and display boards. I invested equally in my content and its presentation!

Like many girls with backgrounds similar to mine, I was pressured by teachers and parents to pursue a more “stable” career in STEM. In my case, academics, medicine or law were perceived to be more financially stable long-term in comparison to a career in design and technology. 

So despite growing up next to Harvard and MIT, it wasn’t until I moved to San Francisco that I even heard about UX/UI design and Silicon Valley. After hearing Aaron Walter (Mailchimp) speak about designing emotional experiences at Designers & Geeks, I decided right there and then that I would do whatever it took to switch careers. UX design allowed me to combine my background and education with what I truly enjoy doing every day.

From that moment, what path did your career take?

My first job in tech was as a Design Researcher. I traveled around the world for Nielsen Neurofocus to open local research labs and collect market research data for companies like Facebook, Coca-Cola, P&G and others. From there, I started moving more towards interaction design and landed a job at Telenav. There, I learned to build navigational interfaces with heavy hardware constraints— and more importantly, the pros and cons of working in a large organization.

Throughout this process, the lack of Black female design leaders in tech led me to question whether or not I could be successful as a designer. I never doubted my abilities as a designer, but I did doubt the capabilities of others to judge me based on my potential rather than my gender and race. I decided to take matter into my own hands by starting Front & Center. The objective was to to empower women of color to pursue a design careers in technology. I worked with amazing folks like John Maeda to define the basic skill set designers need, especially those coming from non-traditional paths (e.g. autodidactic designers).

I did doubt the capabilities of others to judge me based on my potential rather than my gender and race.

While I no longer actively focus on the program (primarily because I realize I could have more of an impact shipping good work), I still mentor underrepresented design talent, and proactively work to connect them to companies with good culture.

This interview series focuses on the different paths into design, and Front & Center aims to provide an “alternative pathway” to it. Why do you think those alternative pathways deserve emphasis?

A traditional design degree is a very privileged path, one that relatively few can embark on. Apart from having the financial means to pursue a design degree, or go to art school - in communities like the one I’m from, there is very little awareness of the possibilities of a career in design. Some of the best designers I know didn’t go to art school or have a design degree— that isn’t the only path.

In order to diversify tech, managers need to learn how to communicate differently and more effectively

In working with design leaders to come up with the minimal skill set required to land a job as a junior product designer, it turns out that the majority of teams don’t actually include a degree as a prerequisite to fill a position. I developed a basic curriculum to develop the skills that were required, and helped students navigate design culture and jargon, mainly to help them withstand the notorious interview processes of tech companies.

In order to diversify tech, managers need to learn how to communicate differently and more effectively with folks from diverse backgrounds, just as much as recruits need a particular skillset. That’s why I’m focusing my efforts more on the leadership side of the spectrum these days.

“Fake it til you make it” is often heard as we navigate these paths, but you’ve mentioned never having a reference point for that. Do you find yourself wanting to be that reference point for others?

Yes. I’ve learned that one of the best things I can do to bring in more women like me into the industry is focus on my work. There are a lot of amazing designers in technology, but very few of them look like me. If my work is great, then I can show others that it’s very much possible to succeed in design as a Black woman.

This industry has historically been unfriendly to underrepresented folks. Why do you think it’s been so difficult to allow diversity to arise as a result of inclusion, rather than initiatives?

I’m fearful that diversity initiatives don’t matter when leadership doesn’t proactively change. When you look at executive teams of most companies, it’s no surprise the rest of the company looks like them. It all starts with the founding team. If that team consists of folks with diverse backgrounds and skillsets, the rest of the company will naturally reflect that. A good example of this is Honor, where the majority of the executive team consists of women of color; this is then reflected in the rest of the workforce.

Intersectionality is key to moving forward, and I hope to bring more awareness about that.

Following on from that, there have been a lot of posts lately exposing tech’s terrible cultures as perpetuated by leadership, Susan Fowler’s among them. What’s an important takeaway from these, for you?

Honestly, I think Fowler’s post resonated with any woman working (in tech). It does feel like an important catalyst for change considering everything that happened afterward. However, I do believe that it’s only the tip of the iceberg. It’s been an important moment for women in tech, but we need to remember that women of color in tech are being treated even worse. Intersectionality is key to moving forward, and I hope to bring more awareness about that.

If you could do everything all over again, do you think your journey would be the same? Would you want it to be?

I would have loved to have gone to art school. But realistically, me nor my parents would have been able to pay for that education; art supplies alone are outside of the financial range of many people. That being said, I’m proud of my journey and the steps I’ve taken to get to where I am today. The one thing I would have done differently would be to show up as my authentic self sooner, and stick to my values.

Historically speaking, people that look and talk like me haven’t always been accepted in white spaces and because of this, I assumed an identity that was safe and non-threatening to others so that I could do what I love doing. While building Front & Center, I discovered my voice and learned that amazing things happen when I show up as myself. To this I say, self-awareness one the most powerful assets for designers.

Is there anything about the internet or technology that you fondly or nostalgically remember from your early connections with it?

First thing that comes to mind is Microsoft Word Art. My brothers and I use to spend entire summers creating our own CDs accompanied with our super fly word art. This may or may not have been entirely legal, but it was a simple and enjoyable process. I enjoyed collaborating with my brothers to curate music, and then create ‘mixtapes; for our parents, friends, or that special person. It felt good to create with and for others and to see their reaction once we showed off our work.

And finally: How do you see your next five to ten years? What are you most excited about? Perhaps most afraid of?

I’m worried but optimistic at the same time. The current political climate casts a dark shadow over many things we’re collectively working on, but I feel that we’ve also reached a point of no return: people are getting more and more aware of the systems that work particularly well for a specific part of the population. People are calling out sexism, racism, and other -isms proactively. People are losing their jobs over heinous behaviour. We have never been more woke as we are today, and I hope this will only improve over time.

Is this where you expected to find yourself when you were a kid in Maryland? If not, where did you think you’d be?

I have memories of being a kid and wanting to work on spaceships: rockets specifically. I thought I would major in “aerospace engineering.” At some point I also thought it would be cool to be a tradesman doing plumbing, electrical, and carpentry type of work.

I took to computers at an early age. In the late 90s and very early 2000s, me and my brother were always tied to my grandmother’s computer. However, I had no idea I would (or could really) work with computers until my high school guidance counselor recommended I take a vocational IT class. There, we learned PC basics, including how to take them apart. That made me think I wanted to work on hardware in some way, and in the years leading up to graduation, I thought I would most likely be a computer repairman.

back then I thought I would hate sitting and staring at a computer all day, “typing.”

After deciding to go to college, that transitioned to this idea of making microchips and circuits (we had learned basic wiring and circuitry in the class). When I did get to college, I took up the “engineering” track of the Computer Science program, and it was that which led me to software development. Ironically, back then I thought I would hate sitting and staring at a computer all day, “typing.” But now, I absolutely love it.

What were the ‘eureka’ moment (or moments) that sparked your journey?

My journey to being a developer started a bit later than some. The first time I ever wrote code was in college!

In all honesty, life just kind of fell together in a lot of ways. In high school when I wanted to be a “tradesman” and didn’t want to go to college, I had a teacher named Ms. Nolan that would tell me (and the rest of the class) “you’re not dreaming big enough” and “you’re going to college and you’re going for free.” I thought she was absolutely crazy.

One day, my guidance counselor told me there was a free spot on a college tour, so I went. The colleges I visited were the only ones I applied to. This is also where I got introduced to my scholarship program - DNIMAS. That was a eureka moment of sorts: Norfolk State University didn’t have a Computer Engineering degree, which was what I’d originally hoped to do. But I wasn’t about to pass up a full ride, so I enrolled as a Computer Science major on the engineering track.

As luck would have it, I thoroughly enjoyed coding and was exceedingly good at it. I remember one day during my first semester: we had just started to really learn to code, and I went back to my dorm room after classes and just began playing with C++ using Dev C++. The more I understood what my code was doing, the more I wanted to write and learn. I was hooked!

This passion got me into some pretty good internships at the Department of Commerce, JP Morgan Chase and IBM. In the end, I took a job from IBM, but I was assigned the most boring role one could ever do: Sharepoint Administration.

The more I understood what my code was doing, the more I wanted to write and learn.

My biggest eureka moment occurred while I was at IBM, when a Google recruiter reached out to me on LinkedIn and I ended up interviewing there.

It was a total culture shock. The type of things I needed to know for college, DoC, JP, and IBM were worlds away from Silicon Valley. I would compare it to working as a car salesman, then one day stumbling into the car factory assembly line and being expected to know exactly how to put the cars together from scratch. I didn’t get that job at Google, but I learned that there was this whole other side of technology out there and I had to be a part of it.

From that moment, what path did your career take? 

I went from thinking “Oh, I have a decent job. If I stay here 5 years, I’ll get promoted” at IBM to thinking, “I need to learn how to be a true coder, how to solve the world’s problems and make the sharepoints, not manage them.”

The first step was to find a job in the Bay area. I applied to a lot of places and didn’t really get much. I ended up falling back to plan Z: switching from IBM to Accenture. It was hilarious, because one of my interviewers even said, “so this is just a business card change for you.” But I moved to the Bay Area with my then girlfriend (now fiancée) and joined Accenture’s SF office, then set out to find a real coding job.

“I need to learn how to be a true coder, how to solve the world’s problems and make the sharepoints, not manage them.”

It was a huge leap of faith. I wasn’t very skilled at the time so I was relatively underpaid, supporting both of us while my fiancée got her Masters degree in Counseling Psychology. Accenture had a wide reach of clients it served and projects one could be placed on and as luck would have it, my Sharepoint hacks done in HTML/CSS/Javascript positioned me to get me contracted on an Apple project (which I actually had to fight for, but that’s another story). Working there as an Accenture contractor isn’t quite the same as working there as an employee, but I still learned a ton. That knowledge allowed me to get into a startup called Yo, which is where I picked up almost all of my backend experience. When that ride ended, I came to Ancestry.

Was there a person, course, or other resource that really helped you along the way? Was your family supportive?

Practice was really my best friend. A lot of what I learned, I taught myself— by trying things and practicing. I have always been curious about how things work. As a small child I would take apart my toys (although they rarely got put back together). Everyone around me was very supportive; most of my teachers (both in high school and in college) saw the potential in me and would do what they could to push me to be as good as I could be.

My family was supportive as well. It was a win-win for them: as I got better and older I became the family tech support guy! All that being said, my biggest resource was probably my scholarship program. I can’t imagine my mom would have been able to afford to send me to college on her own. So without DNIMAS there is a good chance I would have ended up going to community college. I’m sure I still would have made it, but it’s hard to say how much more time it would have taken me.

It was a win-win for [my family]: as I got better and older I became the family tech support guy!

There seems to be a certain pressure on underrepresented folks in this industry to change it from within (while not always being empowered to do so). How do you deal with this?

I feel this pressure as well. I started out by doing things like speaking at my church, going back to NSU and my high school to talk, and tutoring and offering advice to peers and students. I think what I do best (for better or worst) is speaking up about things very loudly. As my fiancé would word it, I “speak [my] truth even if [my] voice shakes.”[1] At work, I’m very outspoken. I’ve developed the type of reputation where people ask me for my opinion when I’m quiet, both because they value it and because it’s unusual for me to not have one.

The hardest part, though, is being consistent and resilient. There are days when I absolutely am ready to quit my job because of the needed change and lack of diversity. However, I always tell myself that if I leave, who will be there to make this change? So I press on and I go to therapy!

[1]Maggie Kuhn

If you could do everything all over again, do you think your journey would be the same? Would you want it to be?

If I could do it all over again, I would probably study harder and try and get directly into a “big name” place like Google. When I first graduated, somehow I just had no idea this world existed, so I would try and do more to get to where I am now faster.

There is, though, a decent chance my journey would have been the same. Because of how life works, I wouldn’t actually want it to be different because of the ripple effects. But speaking in isolation, I definitely wish I could have gotten up to speed faster and thus progressed in my knowledge even more.

Is there anything about the internet or technology that you remember from your childhood/early years that makes you feel nostalgic?

Napster comes to mind. Me, my brother, and another friend of mine use to be really into downloading “stuff.” We didn’t have internet ourselves so we had to perfectly position our computer by the window to “borrow” the neighbor's wifi. Those were the days.

How do you see your next five to ten years? What are you most excited about? Perhaps most afraid of?

In five to ten years, I hope that I’ll look back and think, “man what was I thinking.” I’m all about exponential growth. I flip perspectives very quickly and the goals I have today will likely not be the same in a year.

That being said, ideally I’ll be working on a cause, and less about making money. One of the things I’ve truly come to dislike is capitalism. Most of us work and make money for the sake of survival. I believe that it’s rare to find someone who works where they do solely because of the pure joy they get out of it. Don’t get me wrong, I love writing code, and I do fun stuff at Ancestry— but if I won the lottery, I’d quit that day. But wouldn’t everybody?

The thing that excites me the most right now is crypto-currency and the overall prospect of being able to run my own business - or at least be my own boss. Whether that’s being the CTO of Ancestry, CTO at Sequel, running a Cryptocurrency trading related business, or just having a bot that trades for me while I sit on the beach— I’m not sure.

Thanks so much to Michael for his time and excellent responses! You can find him on LinkedIn. 

Also thanks to /dev/color and their speaker form, which has connected me to both Michael and Nick!

I was only about 4 years old then, so I don’t remember much about it other than that I learned enough to play my favorite games: Reader Rabbit, Pac Man, Tank!, and a few others. When I watch my nieces play with their iPads and iPhone nowadays, I suspect they are far more tech savvy than I was at that age.

At that time no one in my life knew about computer programming. But gamers and coders have a lot in common. They share the same systematic ways of thinking about problems, the desire to optimize systems, and the superpowered ability to stare at screens for hours at a time. So inevitably, my love of games eventually transformed into coding.

What was your ‘eureka'  moment—the one that, if you look back on it now, sparked your journey? How did it feel? Was it “Hello World”? 

In junior high school, I had a friend named Billy, and we were great friends back then because we both loved video games and were both absolute nerds. One day he invited me over for video games at his house. I was expecting Super Nintendo but what I got instead was an absolutely epic re-introduction to PCs.

Billy had LHX Attack Chopper [pictured above], Wing Commander, and Wolfenstein 3D. These were all amazing, groundbreaking PC games at the time. After that, Billy launched a game he had written himself in QBasic. It wasn’t especially complicated but he showed me how he could change the scoring system and game text, then relaunch the game with the changes. Then he used a 2400 baud modem to dial into a local Bulletin Board System called “The Illusionary Forest” and download a copy of Commander Keen.

I was completely blown away by all this. I biked home after that and begged my father to buy a new PC, which we did a few weeks later on a trip to Micro Center.  

Out of all that experience, it was the BBS that stuck. BBSs were a doorway to a much bigger world, where I could be anyone I wanted to, talk to whoever I wanted to, learn more than I could at school. I eventually learned to code so that I could write and sell my own BBS software.

Of course, the first program I wrote was “Hello World” in C++, but I think the real catalyst for my coding career was watching my friend hacking on QBasic and imagining what I could do when it was my turn.

BBSs were a doorway to a much bigger world, where I could be anyone I wanted to, talk to whoever I wanted to, learn more than I could at school.

A bit later, I was also introduced to the idea of starting something of my own, the Silicon Valley dream; I was in a summer program call MITES (Minority Introduction to Science and Technology) hosted at MIT. It prepared me for the school and introduced me to entrepreneurship.

You went from that Maryland/DC magnet school to MIT, then to Microsoft. What brought you to Reddit eventually?

Before Microsoft, I got my first paid internship as an engineer at NASA working on software for x-ray detectors. In school, I became fascinated by AI and machine learning and game programming, and that resulted in my first internship at Microsoft on the Direct3D team.

My first fulltime job, though, was at Microsoft— first working on natural language processing components, which led to learning about enterprise search, information retrieval, machine translation, and machine learning. After that, I jumped into business intelligence where I picked up knowledge about data modelling, data visualization, in memory databases, and advanced analytics. Somewhere in the middle of all that I got my MBA from UC Berkeley, became a General Manager, and started learning about the inner workings of marketing, finance, and business development. Because of MITES, I was continually coming up with ideas with that startup mindset; I always wanted to do something, but it was safer and still fun to stay inside Microsoft and do "intra-preneurial" projects. Now I’m at Reddit and it’s great fun to pick up knowledge about consumer products, online ads, and venture capital.

Going to Reddit was a shock to a lot of people in my life. I had been at Microsoft 13 years and was having one of the fastest career trajectories possible. I’d also built a truly amazing team. I think if I were still there I’d probably be working with my mentor James on how to become a corporate vice president at a large company. But a combination of things finally got me to leave: 

First was a mental shift around how “safe” I felt. I realized that a lot of my energy and motivation came from proving myself through work and that my validation came in the form of promotions and money. But at a certain point, money just stopped being a huge motivator for me and by the time I became a General Manager there was nothing left for me to prove career wise, other than to manage more and more people. 

I realized that a lot of my energy and motivation came from proving myself through work and that my validation came in the form of promotions and money. 

I like learning new stuff and challenging myself but there wasn’t anything on the horizon that excited me.  So, in the months before left Microsoft I was faced with a choice: continue on the same track and be paid a lot to work on a huge new project I didn’t honestly love, or finally chase the dream of Silicon Valley I’d been putting aside for a decade.

Second, Seattle weather. ‘Nuff said. 

Third, living in Seattle made it very hard to see our family. Our brother and sister and live in California but we rarely got to see them, and they were starting to have kids of their own. It made us stop and realize just how isolated we were. At one point the trade-offs made sense, but I could see it in my wife’s eyes that being separated from her family by such a distance was weighing on her.

Somewhere in the middle of all this, Reddit contact me about a VP of Engineering opportunity. The timing was good because my manager at Microsoft was asking me to move into a larger role outside of the Power BI organization. I was already thinking about “what’s next?” and open to taking on something new. I suddenly found myself with an opportunity to make a clean break from Microsoft and get down to the Bay Area. So I handed the reins of my organization over to a guy I knew would take great care of it, and my manager found another experienced exec to run his new team.

I had been looking at other jobs in the Bay Area, but Reddit was the first consumer company. What they needed perfectly matched my skillset: building product teams fast. I’m no longer the best coder around, but if you drop me out of a plane handcuffed and blindfolded into the deepest darkest Amazon, I will crawl out of the jungle 3 weeks later with a kick-ass product team and a working MVP.   

The other thing that “de-risked” the decision for me was a conversation with Steve the CEO where he explained just how much traffic Reddit gets on a monthly basis, the general direction he wanted to head with the business model, and how critical communities are to Reddit. Having launched a few products before, it immediately clicked that his vision would work as long as we could move quickly and carefully.

You’ve mentioned before that “you can’t go home again” after life changes so much. How do your parents perceive your career now, after laying such strong foundations for it?

They are astoundingly proud but I’m sure they have no idea what I do. I know they aren’t on Reddit or Power BI users. Whenever I go home my family asks me to help them install Office or debug their machines. But I think that’s true for a lot of people who work as software engineers. 

The other thing it took me a long time to realize, being so focused on my own career, is that my parents never really cared how high I got in the corporate world. When I was at Microsoft, they didn’t understand what a General Manager was, or show any interest in the fact that had come to have a large team with employees around the world.

My mom was a school teacher and my father a public defender. I have yet to meet two people who are more selfless and satisfied with what they have. They only ever really cared that I was doing my best for the people around me. 

Do you ever feel pressure to be a mentor, an example, or a role model for underrepresented folks in tech?

I feel a lot of pressure to be a good person. I’ve had a very fortunate career with an unbroken string of supportive managers and great opportunities. The great thing about being where I’m at career-wise is that I can do pretty much whatever I want now. I don’t need to prove anything to anyone or chase money.

So when I try to mentor, give back, or write a blog, it’s because I actually think it is important to help other people. Tech careers are today’s gold rush, and I want to make sure that women and minorities have access to the opportunity.

If you could do everything all over again, do you think your journey would be the same? Would you want it to be? 

Looking back on my early career I thought of Microsoft was a “safe” job where I could build a career and fortune over time. I equated money with a safety net that would allow me to take on more risks. But now I realize that I always had something even more valuable: time and motivation. When you are early in your career, time itself is a safety net. You can take on risks, try a lot of things, and if it doesn’t work out you can try again. Because I didn’t have this mentality, I passed on great opportunities that would have made the entrepreneur in me happy. 

Second, I am a total workaholic. I put all my energy into building software with little to spare for thinking about kids or family. But eventually I came to understand that tech projects are sandcastles. Even the most beautiful and carefully designed system is meant to be swept away and replaced someday. Looking back, I would have learned to balance work and life more carefully.

Nowadays I work at Reddit where the company culture makes it hard to fall into that trap, and my wife also gives me a back-of-the-hand slap if I’m spending too much time on the keyboard.

"Roy Rogers is terrible but nothing beats the spice of nostalgia.” Is there anything about the internet or technology that you remember from your childhood/early years that gives you the same nostalgic feeling as Roy Rogers?  

I hate to age myself this badly but Usenet, IRC, BBS systems, MUDs. You could be pseudo-anonymous and because of that you could connect with people in ways that weren’t possible in real life. But something got lost along the way from the development of those early systems to modern social networks. It could be the nostalgia speaking but the connections with total strangers I met on BBSs, and even AOL, felt more real to me than most of my Facebook and Twitter “friends.” The early internet was maybe slower paced and harder to get into, but the result was a deeper sense of community.

total strangers I met on BBSs, and even AOL, felt more real to me than most of my Facebook and Twitter “friends.”

Reddit works because of great communities. I think it has the potential to bring back that spirit of the early internet and make it available to everyone on the planet.

How many steps did it take you to become an C++ expert in the end?¹

I will proudly say that I have written software in C++ that is today used by a good fraction of humanity. But I will never say I’m an expert in C++.

Thank you so, so very much to Nick for his time and thoughtful responses to my questions. I originally reached him via the dev/color speaker request form. A lot of this interview was sparked by his piece From “Hello World” to VP Eng, which you should most definitely read. You can also find him on Twitter.

Talk about some recent projects. How do you come up with those crazy ideas, and how do they become reality?

Usually it’s a random mix of things. Sometimes it’s another reporter going “Hey look, this health agency publishes emergency room waiting times on their website, what if we did something with that?” which led to an app called ER Wait Watcher. Other times it’s an editor saying, “We have this complex cast of characters for a story about narco-terrorism, what if we made it into a comic?” which also turned into an interactive piece. And sometimes it’s just me surfing the internet and stumbling upon a French researcher’s website that happens to have county-level presidential election results going back to 1828.

Above: “The Making of a Narco-Terrorist,” a ProPublica interactive examination of whether the DEA is stopping threats or staging them. 

The latter was probably my favorite recent project, a piece called Lost Cause that we published right before the election. It framed past American elections through the lens of the losers: showing maps of who voted for the candidate that ultimately lost. The best part was interviewing a bunch of historians and geographers about what was going on in the country at the time and what they could “see” in the maps. Those conversations were endlessly fascinating (pro-tip: interview academics as much as possible – they are extremely eager and excited to talk to you about their work!)

Above: The “Lost Cause” project, showing past American elections from the standpoint of the loser. 

On the technical side, creating almost 50 maps for the piece was an interesting challenge, because not only did we need to map dozens of election results, but we needed to create historically accurate maps that corresponded to each election year. Turns out shape of the country has changed a lot since the 19th century (who knew!) and each year the county boundaries were slightly, or in some cases drastically, different.  

Thinking back, what was your ‘eureka' or origin moment?

I went to graduate school for science journalism, thinking I would write long articles about discoveries in neuroscience and psychology (I was really into that stuff in college, but didn’t want to be the one in the actual lab doing the actual work). I had never heard of data journalism or data visualization, and I certainly didn’t know that people working in news made graphics for the web. But when I found out (right around Hans Rosling’s famous wealth & health of nations video) it was instantly appealing. I had always really loved graphic design (mostly in a print context, posters and such), and suddenly here was this thing in journalism that let you tell incredible visual stories and meant that I could sometimes use Photoshop? I was so in.

One of the requirements of NYU’s science journalism program was to do an internship over the summer. I did mine at WIRED, and the vast majority of it I spent writing articles for the the Danger Room blog about drones and spies and other sci-fi worthy military projects. Somehow my editor Noah Shachtman agreed to let me do a data visualization project for the ten-year anniversary of 9/11 (keep in mind I had not published a single other graphic and all Noah knew was that I was capable of Photoshopping words onto petri dishes and chickens onto tanks).   

suddenly here was this thing in journalism that let you tell incredible visual stories and meant that I could sometimes use Photoshop? I was so in.

But we did it, and the final graphic was an attempt to tally up the cost of the war on terror. I realized at that point that this was precisely what I wanted to spend all my time doing.  

Above: ‘The Dead, The Dollars, The Drones’, Lena’s ‘eureka’ moment. 

What path did your career take from there? How do you find yourself where you are today?

It wasn’t long after that I started an internship at ProPublica. It was a writing internship – I was mostly writing stories about health and the environment. But every so often I would pitch a visual idea to Scott Klein, the editor of the data/graphics team (or “news apps” team, as we call it), and ask if I could design and build it myself. The first one I ever did was a side-by-side comparison of two types of airport body scanners. Then a fellowship on Scott’s team opened up and I moved across the office, and a few months later was hired full-time as a news apps developer.

Turns out that to make news graphics today, you need to know how to code. Whether that’s Javascript, R, Ruby or some other language often depends on the project, but knowing at least one programming language and being open to learning more is pretty important. When I stumbled into data visualization I knew only maybe a tiny bit of HTML and CSS. So my first year at ProPublica was a crash course in all kinds of programming challenges that I now encounter all the time but then were totally new: how to scrape a website, how to put dots on an map, how to make an interactive chart.

each project is less “Holy shit I have no idea how to do that,” and more “I’ve solved this other problem, I can probably do that one too.”

That year was probably the most insane and frustrating and rewarding year of work in my life. I was very lucky that ProPublica in general and Scott in particular care a great deal about giving reporters the time and space they need to learn new things. And it has its benefits – I joke with Jeff Larson and Al Shaw (two developers on our team) that they’ll never have trouble reading my code because they literally taught me all of it.

These days, I’m still learning a ton of new stuff for every project, but I’m familiar enough with the basics that each project is less “Holy shit I have no idea how to do that,” and more “I’ve solved this other problem, I can probably do that one too.” So, for example, when we wanted to make a visualization of human body parts for a project about America’s disastrous workers comp system, I was able to cobble together some pieces of code plus some shapes I made in Illustrator into an interactive that worked. For more on that project (I’m sure some of you may have a question or two) here’s a longer explanation.

In general, I’ve also gotten significantly better at Googling for the answer – that’s not nothing. 😜

Do you think that this convergence of data, design, and journalism is the way forward for the news industry more broadly?

I don’t want to make any sweeping predictions about the news industry, but I do think having data, programming and design skills can make you a better journalist, for a bunch of reasons. Here are a few: first, knowing a bit of programming lets you find and tell stories that no one else can.  If I had to copy and paste all the data that went into this project about health and safety problems on cruise ships, it would have taken me years (not even kidding). But knowing how to scrape a few websites let me grab all that data and sort, filter and analyze it into its final form.

knowing a bit of programming lets you find and tell stories that no one else can.

Second, having some data wrangling skills let’s you verify information on your own – you aren’t dependent on PR people or government officials to tell you what’s true. You can see for yourself what the data says! (That said, it’s probably a good idea to talk to a bunch of experts and do enough reporting to back up what you find).

Finally, knowing a little bit about design helps you create projects that are easy to understand and use. Most people know how to read a story that’s made entirely of words. But some of the interactive graphics and data visualizations making their way into the news these days are pretty complex, and being able to design them in a way that’s easy to follow and also tells a compelling story is important. That doesn’t happen by accident – designers spend a lot of time thinking about the user, ideally testing out different approaches on real people. Constantly keeping the user in mind usually makes for better journalism.   

You teach design and data visualisation as well; what prompted you to do this, and how have you found the experience of teaching?

Teaching is both much more difficult and much more fulfilling than I ever thought. It’s really amazing to see students applying the things you’ve mentioned in class to their own work, or getting them super excited about a new technique or a chart form they’d never seen. Then again, it’s really humbling to realize that even though you thought your lecture about, say, design principles was awesome and intuitive and the best explanation yet, some students are still totally mystified. It’s always a learning process for me also, since I’m constantly reworking lectures or tutorials to make them easier to follow or adjusting exercises to better capture the ideas I’m trying to explain.

One thing I do try to do is make all of my teaching materials, slides, etc, totally public and free for anyone to use. I’m constantly learning from free online resources, and feel like it’s important to put materials back into that space for others. We do this at ProPublica too, my colleague Sisi Wei and I run a 2-week workshop called the Data Institute, and put our entire curriculum up online for anyone to look at. It’s not the same as being in a classroom for 2 weeks, but it’s a way we try to give more people access to what we teach (at no cost to them).

A final note on teaching: showing students the Web Inspector for the first time is always a joy. That collective gasp probably makes the entire class worth it.

Finally: if you could do everything all over again, do you think your journey would be the same? Would you want it to be?

I’m sure if I did everything over again my journey would look very different. It’s easier to tell a nice linear narrative in retrospect, but along the way my path felt very random. Even going into journalism in the first place feels a lot like an accident (I applied to NYU after a good friend told me about the program, and just happened to get a full scholarship to go). But I do think I would have eventually come across data visualization, especially now that it’s become so much more mainstream. And it was probably inevitable that I was pulled towards some combination of design and writing.

And what about the future?

We’ll have to see! Luckily the intersection of journalism, technology and design is so broad that I don’t think I’ll be bored anytime soon.

Anything you’re particularly excited about?

I really like gifs that explain things.

What’s your day-to-day like? What’s your favourite part about it?

Depending on what’s going on in the rest of the Financial Times, my day might include:

working through some problems with a designer

making sure Origami is represented in the FT’s technology business plan

running a workshop on using Origami with some in-house developers

writing a conference talk

meeting with other people at other companies to talk about the ways they’re solving the same problems that we’re trying to solve

Maybe, if I’m lucky I’ll get to write some code! Writing code is how I got to where I am now, and it’s always something I’ll enjoy doing, but with my current job it’s actually only fun if I know I’ve handled all the other things people are relying on me for.

Above: Origami, the Financial Times’ component library.

My favourite part of the job at the moment is working with the design team. They’ve seen a lot of churn recently, but as a result we have a lot of new designers who are really strengthening Origami and it’s great fun to work with them and improve stuff together.

You say your job is “part developer, part advocate.” What does that mean?

That used to be my job role; when I joined the FT I was hired to do outreach-y stuff for Origami — make sure people in other teams knew how to use it and how it could help them. That was about a year ago. About three months after that, the person leading Origami left, and I got his job. So now I’m leading the team and setting the direction.

In terms of discovering your interest in development, what's was your ‘eureka'  moment—the one where, if you look back on it now, sparked your passion?

This is such an uninspiring answer, but I just kind of fell into it. I did an A-level in computing, and then a degree in Computer Science, and then in 2007 I discovered web development, which was just this really fun place to be. I remember meeting a few people from Last.fm and thinking, “Wow, these people spend all their time creating a website for people who love music— how can that possibly be a real job?” 

I think it’s dangerous to suggest that people need a “passion” do development. 

I then went to a conference called Interesting, which was loads of people from the web talking about things that interested them. Anna Pickard, now a creative director at Slack gave, a talk about all the funny words she could think of which was extremely entertaining.

There was no eureka moment. I think it’s dangerous to suggest that people need a “passion” do development. You can be really good at web development, or any job, without needing it to be a passion. If you can align your job with your passion then that’s great but I don’t think many people can.

After that degree in Computer Science, what was your journey like? How did you come to find yourself at Origami?

After my degree I joined a 5 person company called Assanka. I had a choice between them and a graduate position at IBM. This was a risk; I was joining a company of 5 other people, fresh out of university, the only woman there, I didn’t know much about them, and didn’t know any PHP which was what I’d be writing. But I spent 2 brilliant years at Assanka learning how to code and learning how websites work, and it all worked out fine. I’m still friends with most of the people from that company today. My PHP is still terrible.

This was a risk; I was joining a company of 5 other people, fresh out of university, the only woman there, I didn’t know much about them, and didn’t know any PHP

After that, I joined a product invention company called BERG. That was an amazing job and I loved working there. We made an IoT cloud connected printer called Little Printer. It was a really fun project to work on. After BERG, I went to the Government Digital Service, where I stayed for 2 years.

GDS gave me the source material for my first big conference talks. When I joined I thought, “Hang on a sec, there’s some really interesting stuff happening here, and I should really go out and tell people about it.” From there I went to the Financial Times, which is where I am now.

Above: Little Printer, by BERG

What prompted you to start tampon.club? What’s the best thing to come from it so far?

I started Tampon Club out of laziness really. I just wanted to be able to keep my tampons in the toilets at work and I thought the most sure-fire way to do that would be to start a tampon co-op. Once I realised it was actually quite popular, I set up a website in case other people would like to start one at their office. http://tampon.club allows people to set up Tampon Clubs anonymously as they can just include a link back to the site for people to find out more.

My favourite thing about Tampon Club is people emailing me to say, “Thanks, I needed a tampon and Tampon Club saved me.” That’s incredibly cool.

If you could do everything all over again, do you think your journey would be the same?

Yep, probably!

Do you ever feel pressure to be a mentor, an example, or a role model for women and minorities in tech?

At work, because I lead a team, I feel pressure to set an example in general, but not specifically to women or minorities. I’ve realised that (and it was actually my friend Anna Shipman who really drummed this into me) I don’t have to mentor other women just because I’m a woman, and it’s not my job to do that along with all the other stuff.

I used to feel like I had to say yes to every opportunity, partly because I hate saying no to people, and partly through FOMO. Seeing Anna turn down things that she would be good at— and maybe even enjoy— because she recognised she had other commitments that would suffer, showed me that it was OK for me to do that too. If anything, it makes people respect you more because they know that if you say yes, you’re going to work really hard to make that thing a success.

The things I’m most likely to say yes to are always requests from underrepresented people in tech. But there’s no pressure with that, I just think those things are the most important.

What was your first talk like? Were you comfortable giving it?

I gave a 15 minute talk about my job as a Creative Technologist at the time [at BERG]. It was an evening event, which I don’t remember the name of. I was incredibly nervous, but it was a lot of fun and I’ve gone on to give loads more since.

Someone in the audience tweeted that my project was “hipster trash”, which I was quite upset about at the time, but it taught me early on to not shit on other people’s talks from the audience, even in a subtweet.

What do you enjoy most about giving talks?

There’s a lot I like about it. I have friends all around the world who I met at conferences. I’ve made massive work breakthroughs, because the act of writing a conference talk has made me think about problems in a different way. I like being on stage, and I like the bit afterwards when you’re glad it’s over.

Is there anything about the internet or technology that you remember from your childhood/early years that makes you feel nostalgic?

I was 13 when we first got the internet at home, and I had to use my mum’s work laptop to use it. I have some very nostalgic feels about the MSN messenger emoticon set.

How do you see your next five to ten years? What are you most excited about? Most afraid of?

Next week I’ll turn 30. I hope the world is still here in 10 years time. I’m worried about the oceans and the boiling-frog-style creep of fascism.

You hoped to be a vet when you were a kid. When did design enter the picture?

I think, rather than one particular moment, it happened slowly over time and then all at once. I was fortunate enough to grow up in a household with a computer and in a really supportive family that viewed my art as if it were fresh from Picasso’s hands—every grandma gawks over a stick figure with no neck, right? That appreciation for art and beautiful design carried over into high school, to the point where I only brought my sketch-book to class and used that to jot down my notes, while continuing to sketch everything from still life to concept cars on the other side.

One experience I remember is being tasked with redesigning a soda can in class. It was the moment I discovered that I can take what I’m putting on paper and digitise it, and I loved the endless possibilities that came with that. It was history from there. 

And what did your journey look like after that?

From there it was a roller-coaster of events. I went to school as a bio major for a few years and never thought to actually take up design or attend design school, even though I’d dabbled in design since high school.

I didn’t think of it as a career, because I didn’t think design would allow me to support myself and live comfortably. I grew up in the kind of middle-class family who doesn’t jump off the cliff without making sure the parachute works. I also didn’t equate risk with reward. In this industry, reward doesn’t even seem to exist without (calculated) risk.

Eventually, I understood that not only was there more to design in terms of how passionate I would become, but also in terms of how much money I could make. That said, by the time I got into it full-speed, the money wasn’t even something I cared about.

I grew up in the kind of middle-class family who doesn’t jump off the cliff without making sure the parachute works.

I freelanced in college but I couldn’t shake the mindset from before— that I couldn’t support myself by working in design— and ended up in education. I needed a backup plan, and that was it. I worked for the New York City Board of Education and, while I loved working with kids, I knew that if I stayed I’d be miserable, because it wasn’t what I wanted to do for the rest of my life.

When did you finally realise that design could sustain you?

Around 2010, maybe 2011. Dribbble was really big, my activity on there was growing, and I had really started tapping into the Twitter design and tech community. I was at my computer and thought, “I can’t go back to work and keep doing this.” I was waking up at 5 in the morning to go to work, and for what? I wasn’t happy. There’s only so many days you can do that while knowing good and well there is another viable option.

Right then and there, I decided that I was going to quit. I lined freelance clients up the wazoo to ensure that I wouldn’t be on the street or back at grandma’s house— at least not immediately. I took the plunge and from there, the rest was history.

I was naive to say the least, but I had a plan and I made sure to execute on it, and learned my best lessons. I’ve been fortunate enough to get my feet wet in a variety of areas that really taught me the ins-and-outs of being a designer—from corporate design to agency and freelancing. I had a couple “lovely” (read: nightmare) clients, lost out on quite a bit of money, created a few not-so-gorgeous websites, burned out once, learned my lesson there as well and never did it again. 

Then, I decided to really jump off that aforementioned cliff without a parachute. I founded my first startup, Liberio: a simple eBook creation and publishing platform for self-publishers.

All of those events had their own individual “aha!” moment for me that pushed me toward the next. I’ve learned a ton of lessons from each of them:

Much like a game of chess, take time to understand the different scenarios before jumping the gun.

Take 50% from the very beginning with freelance clients.

Bootstrapping is ferociously difficult and extremely gratifying. Do it for as long as time allows, so long as it doesn’t compromise the product or team.

God is in the details

Experimentation and exploration are necessary for any form of innovation.

As a small team, you’re either fundraising or building. Understand when one should be prioritized over the other.

Create a brand and product people can trust and fall in love with.

Any second thoughts along the way? 

Never. I’ve loved every minute of it.

Have you become more comfortable with taking risks? After all, you’ve founded several startups now.

I did spend a lot of time wondering, “what if I’m not good enough?” “What if they fire me?” That imposter syndrome reappears here and there, but with time and experience it’s certainly occurring less.

When I started Liberio, the fear that came with it was something I hadn’t worked out personally yet; where I come from, failure is not necessarily something you strive for. Now I know that while I don’t strive to fail, I do know how to bounce back, and the praise is in the comeback. In the lesson. With Liberio, I felt super-inclined to write about failure because I felt like that was the only way to save myself from it and—if we’re being honest—save face to a good extent. I could then hide away somewhere while I figured out how to bounce back and really work through each lesson learned.

Now I know that while I don’t strive to fail, I do know how to bounce back, and the praise is in the comeback. In the lesson.

Switching gears a little bit: do you ever feel pressure to be a mentor or role model for other women in tech? 

I think pressure would be the wrong word, mainly because I don’t see it as a burden and I don’t question who I am as an individual and my core beliefs any longer—in work and personal areas. I like to think I carry myself, live my life and conduct my business in a way that is quite decent and isn’t dependent on any particular situation.

However, I’m still growing as an individual and if I screw up, it’s because I’m human. We all do, and that’s important for others to see, as well. All in all, I absolutely love the idea of being or knowing I am a mentor for other women in tech. It’s a major honour.

Would you encourage those new to our industry to find mentors? You’ve had a few yourself.

Yes! I am where I am because of the people who I’ve shadowed and paid attention to throughout my life. This especially applies to those folks outside the industry. For example, I have a friend who is not on the internet. From her, I learn the value of detachment and tranquility. 

So yes, find mentors, find advisors, but find them across the board— both inside and outside of design and tech. Speak to doctors, to social workers— you’ll learn so many different lessons. But remember, too, that all advice needs to be filtered and applied so that it works for you; the ability to manipulate and tweak that advice into what works for you is an important skill.

find mentors, find advisors, but find them across the board— both inside and outside of design and tech

What are your general thoughts are on diversity initiatives’ direction and progress?

In the past, anything that has been changed or fought for with change in mind, has started with conversation— to the point where having conversations, to some, might feel like beating a dead horse. But it needs to be continually talked about and continually present in everyone’s face, to the point where you’re unable to run from it.

For a single white man, the sky's the limit. For the underrepresented, the limit is the sky all too often. The goal is to make it so that one day, the former is true for everyone. There’s still a long way to go, but the good thing is that the roles and positions and opportunities are starting to become available. Companies understand the role they play in changing the status quo. Not to mention, the companies benefit immensely with a diverse team. I’m part of a large group of underrepresented people — women — but not the most underrepresented and I can’t imagine what that is like. So as long as whatever group you’re part of and we all work together, I hope we’ll get there eventually and I’m always willing to help wherever I can.

For the underrepresented, the limit is the sky all too often.

You’re a new mom. What has it been like to strike that new balance?

It’s funny; a lot of people ask “How do you do it?” and some seem genuinely curious, while others seem like they don’t believe it’s possible. Why shouldn’t it be possible? For me, it’s not even a question. Having my daughter taught me how to maximise productivity within the hours that I know I have. So while I have less time, I’m significantly more productive, because I know I won’t be able to do it later. I’ve never got more work done and felt more healthy physically than I do now.

Those are the people you want to work with, the people who understand the meaning of true value and respect for another human being.

I don’t understand the hesitation in this industry when it comes to hiring women with children; I know that my husband certainly values and prioritises the same way that I do. For me, if anyone, male or female, knows how to prioritise and balance having children and full-time work, to me, they’re a hell of a team member. Those are the people you want to work with, the people who understand the meaning of true value and respect for another human being.

When your people succeed in their personal life because your company sets up a support system to make it easier for them, your company succeeds. Every time.

If you could do everything all over again, do you think your journey would be the same?

Definitely. I’m really happy that I took the course I did. I have a pretty diverse skill set; having worked in special ed and studied psychology in school, I feel like it gives me the empathy and patience needed when building a product that will has direct impact on someone. The patience part definitely teetered off a bit, but I’m getting there again.

Is there anything about the internet from your childhood/early years that makes you feel nostalgic? 

Probably a few things off the top of my head: Using the internet to replace the encyclopaedia for the first time, the Oregon Trail game (my first digital entrepreneurship), Winamp, Adobe Dreamweaver for website building (cringes), that damn ‘You’ve got mail’ sound, and creating 8-bit characters in MS Paint.

I remember once thinking that I wish there was a way to digitally enable the creation of thin and thick paint strokes (pressure sensitivity). If I wasn’t such a little one at the time with thoughts as fleeting as the wind, I’d probably be kicking myself in the ass for that now. Then again, I wouldn’t have even known where to start.

Where do you see yourself five years from now? Ten?

If you would have asked me this 5 years ago, my answer would be so far off from where I currently am. I’d be lying if I said I knew this is where I would be. In 5 years from now though? Hopefully with my family, enjoying life, building a company that makes a difference in the lives of many people. I have a little one now, so that makes life a bit more predictable.

Who am I kidding? It’s the most unpredictable and wonderful journey I’ve ever been on...

This one’s been in the works for a long time now; thanks so much to Cat for her dedication and patience! I look forward to a drink together one day! 

You have a degree in math— did you expect to find yourself in web development when you were a kid? If not, what did you expect or aspire to?

Web development didn’t really exist when I was a kid — at least not professionally. I was born in 1989, so I’m just a little older than the consumer web. Anyway, what I wanted to be changed, from fairy princess to ballerina to president to physicist. I entered college just happy to have gotten in somewhere, with absolutely no idea what I wanted to do. I remember sitting through a pre-med info session and realizing that I wouldn’t get to take a single fun course all four years if I did that. In my first semester, I signed up for two math classes, intending to drop whichever one I didn’t like. I loved them both.

However, I failed out that semester — I had a weird episode where I refused to go to class for two months. I came back the next year, though, and declared math almost immediately. It was fun, and there was something about the fact that I had never focused on it before that made it easier for me. I could coast elsewhere, but not in math.

What was your ‘eureka’ moment—the one where, if you look back on it now, sparked your passion?

Actually, there were several courses I took that gave me a taste for problem-solving: discrete mathematics, real analysis, and topology. They all involved doing a lot of mathematical proofs. Just like software programs are either error-free or not, proofs either are sufficient or not, and I enjoyed that lack of ambiguity.

In discrete math, which I took my first term, the professor gave us all the proofs we would have to do throughout the semester at the beginning of the term, and I started working through all of them as fast as I could. I’ve by no means retained the finer skills, but it was invaluable to learn how much joy there is in solving mathematical problems.

I really regret that my math education before college wasn’t fun. I went to a big math-science high school full of high achievers, where I always felt inadequate. Math and science classes were particularly stressful and also had the lowest quality of teachers; a graduate degree took priority over an interest in instruction.

I’ve by no means retained the finer skills, but it was invaluable to learn how much joy there is in solving mathematical problems. 

What path did your career take after that?

I spent school thinking I was going to become an academic, but honestly I wasn’t good at it; my first summer spent researching, I had a total freakout and wasn’t productive. The second summer, I was solid, but not a star, in the production of the paper we wrote.

Fortunately, there’s this thing called software, which is doing logic puzzles for money. I did a software internship at the publishing company where my parents had worked. The work was pretty straightforward: Perl scripts to sort XML files, Java/Spring/Hibernate web dev on internal tools. I learned vi, the shell, MVC, and SQL. You can’t do better than that for a first job. I was also taking computer science theory classes at school, which meant that I was at least passingly familiar with stuff like regexes and graphs, which would come in handy later. I wish I’d applied to one of the big companies for an internship, but my school didn’t have a culture of it.

there’s this thing called software, which is doing logic puzzles for money.

I found it hard to find a job when I graduated. I was pretty unfocused and unhappy, but a few months later I went to one of the first boot camps in Boston. This was 2012, when they were still pretty new. I immediately had a few decent job offers after finishing, and I chose to go with a small startup in the educational technology space. Boundless’ business model was bundling open educational content into textbooks. When they hired me, they were being sued for copyright infringement by three textbook publishers. It was a great place to work. My first boss, the VP of Engineering and later the CTO, always believed in me, and that has been crucial.

I left Boundless because I wanted to move home to NYC, but immediately I fell into awful job misadventures. I knew no one in New York, interviewed fitfully, turned down the best offer I had because I had a Facebook interview the next week that I failed, and yearned after one particular startup which strung me along and rejected me. Eventually, I took a pretty mediocre job which I was immediately poached out of to be the first engineering hire at a company that literally billed itself as the Warby Parker of makeup to its investors. 2014 was peak “Warby Parker of X” time. I think they hired me because I fit the office aesthetic they were going for, but unfortunately I’m not photogenic and I was agitated by all the crying in the office, so within a few months I had to switch jobs again.

My first boss, the VP of Engineering and later the CTO, always believed in me, and that has been crucial. 

Thankfully, the switch was easy this time; I had gotten to know and admire Camille Fournier at Rent the Runway, and wanted to work for her. I did that, but she left two months after I joined the company. For a time, I worked with nice people and built React stuff, but I didn’t really see a path to what I want to do, which is engineering management. I was the most senior female engineer, and the degree of the company’s investment in its web team was uncertain. Anyway, I was ripe to be plucked by BuzzFeed, which offered me a female boss, massive user numbers, and a very nice selection of couches to code on.

You do a lot of speaking at conferences and events; how did that start?

In early 2013, I saw Lea Verou speak at an otherwise pretty mediocre frontend conference in Waltham, Massachusetts. A co-worker of mine pointed her out and said something like, “That could be you, if you wanted!” Lea gave a very interesting talk about the W3C’s working process, and it was just cool to see a young woman up there on the stage in that male-dominated space.

Nonetheless, it took me until the spring of 2015 to submit a PR to Brooklyn.js. At first, I submitted a meaningless proposal about Angular controllers, but the organizers were and are extremely proactive. They sat down with me and helped me realize that the story of what I was doing at work — being the only engineer in the organization — was much bigger and more interesting than any specific technical question. At Mariko Kosaka’s suggestion, I submitted it successfully  to JSConf EU. There, I hung out with Lea Verou, so everything came full circle.

Do you ever feel pressure to be a mentor, an example, or a role model for women and minorities in tech?

It’s not pressure — it’s a moral and professional necessity, but not just because I’m a woman. If you refuse to do mentorship work when you have the opportunity to do so, you’re really limiting the impact you can have on your workplace and community.

the concept of a role model has been distorted by [a] lack of representation.

While mentorship is a duty, an opportunity, and a joy, I have to refuse to be a role model. I see how the scarcity of women in this industry makes us visible in a way that is often uncomfortable, even threatening, and the concept of a role model has been distorted by this lack of representation. Mentors are people who offer resources they have, like teaching time and connections, to help people grow professionally. Role models are people whose existence provides a model of who you could be and how you could get there. My behavior and perspective are both my own, and the idea that someone might use me as the basis for a preconception of how women should behave in this industry feels wrong.

If you could do everything all over again, do you think your journey would be the same?

I am hardly immune to wondering where I would be in life if I had managed to keep my grades up in high school, but yeah, I would still be in tech. As things are, I’m really happy with the way things are turning out for myself, and grateful for the opportunities I’ve had.

Is there anything about the internet or technology that you remember from your childhood/early years that makes you feel nostalgic?

Who else played Kid Pix? My parents had a lovely early nineties Mac with a CD drive that popped out. I used it to play Kid Pix, and the manhole game, and Colonization. Later we got a Windows 95 Compaq which was pretty sick because my brother and I could play Spelling Jungle and Lode Runner. I couldn’t win Civilization II at harder than, say, Warlord difficulty — so obviously I’m a fake geek girl.

I wonder what percentage of people who write code for a living had access to a late-model PC and an Internet connection growing up. I had that, plus a mom whose nickname at work was “Susie Software.”

How do you see your next five-to-ten years? What are you most excited about? Perhaps most afraid of?

I am most afraid of global warming, obviously. Second scariest is that Trump somehow decides to kill net neutrality, starting a chain of events which leads to me losing my job. Please, try not to think of how many logical leaps my anxiety is capable of making.

there’s no point in going to Mars if we can’t even terraform a little desert like the Sahara

There are things to be excited about. Web technologies are growing more powerful all the time, and more and more people are learning how to access and work with them, and inventing the future as they go along. I still think it’s crazy we’re working on this instead of spaceships, but hey, there’s no point in going to Mars if we can’t even terraform a little desert like the Sahara.