Stochastic Outlook

I've always been friendly with my neighbors. I try to bake cookies, leave post its, and say “hello” in passing. I took pride in being close with my neighbors. It’s because I am a Chatty Cathy with too much West Coast Nice in me. This didn't go as planned in New York. The first week I moved into my apartment I set my oven on fire and met my neighbors under arsonist circumstances. My housecleaner forgot to clean the puddle of grease at the bottom of my oven and it caught on fire when I tried to bake salmon croquettes. Siham rushed out of her apartment and ran to the fire station for help while I dialed 9-1-1. Luckily, we lived right next to a fire station.

People told me New York is full of independent, successful, badass women. I didn't believe it until I met Siham. She's not your Sex in the City type of NYC power bitch. She's humble, smart, inquisitive, French Moroccan, and fiercely independent.  She's not dressed in designer clothes like a lot of the girls in Chelsea. Instead, she's a minimalist with no make up who dresses for comfort.

In the past few weeks, Siham quit her lucrative pharmaceutical job, became a US citizen, and sold and donated all her belongings. Today she is on a bus to Yorktown where she will bike across the country with all her worldly possessions in two panniers. This journey will take 3 months to finish 4228.5 miles.

I never thought my neighbor would leave such an indelible mark on me. I've never met someone who is so committed to living her authentic self.

Since moving to NYC, I've been thinking a lot about the narrative of the modern woman. She is not just a wife or mother. She not just a pretty woman to look at. She is not a woman who depends on male attention or financial support. She is many things. She can bike across the United States after selling all her worldly possessions, she can volunteer to mentor impoverished women, she can quit her job when it's unfulfilling, she can leave relationships past their expiration dates, she can live alone in her own apartment, she can be financially independent, and she can reject what society tell her to be. Siham is the type of woman that inspires me to find my own life path. She helped me assemble my bed frame when I hit my NYC blues. I didn't realize that I had depended on previous boyfriends to help me with handy work and furniture assembling. For the first time, I was alone and didn't own a power drill. I felt so helpless and lonely. After feeling sorry for myself, I bought a power drill and assembled my midcentury bed frame together with Siham. We walked out into fresh snow and had the most delicious udon after a hard day of drilling and nailing. When I was feeling lonely during my first NYC winter she would drop by and check up on me with a croissant. She always knocked and said “Hello neighbor!” in her French accent. While I was lamenting about how hard it was to meet new friends and date in NYC, Siham recommended me to do what I enjoy like taking a cooking class or volunteering at NY Cares. When I lamented about how private and cold the other tenants were in our building, we joked about hanging signs that say “Don't forget to say hello to your neighbor!” like in the episode of Seinfield.  Siham made New York a little softer and less lonely for me. Over the past months she got rid of all her possessions. She reminded me that less is more. You really don't need all that stuff. Inspired by her immaculately clean and uncluttered studio space, I ruthlessly konmari'd and donated my clothes this winter. She was right — when you have less things a Chelsea studio apartment feels more spacious. I didn't feel so cramped anymore compared to my spacious SF apartment. When I struggled with my singlehood she reminded me that women are so much more than just being a girlfriend, wife, or a mother. She wasn't defined by a label nor did she pursue such labels. Her self worth was not contingent on her ability to procreate or keep around a man. She had serious relationships too but they didn't work out and that was okay. She reminded me that the modern woman is many things, far more than what society defines us. She helped me see that I was was living for other people's expectations. I didn't have to be a slave to my traditional Chinese upbringing or social expectations. On our last night together sitting in her empty apartment, I lauded Siham as my version of Cheryl Strayed from Wild. She laughed and shirked my comment. The thing about Siham is so humble and so brilliantly smart. She won’t blog about her journey so it doesn’t distracting her own personal journaling. She calls me out on my American tendency to story tell and my obsession with revisionist history. Siham is the modern woman whose narrative is yet to be written. I'm so glad that I met her. I'm sad that Apartment 5D will never the same. Thank you Siham for reminding me to be different. Dare to be different. We are the first generation of this kind of woman whose traditions, values, and stories are still being written. I cannot wait to read your story Siham.

I’ve suffered from perfectionism since childhood. I would start something, stop, and do it over because I didn’t like the way it looked. I would painstakingly perfect my handwriting on my homework assignments which took way too long. One thing I learned quickly by middle school is perfectionism can be crippling. Perfectionists start many things and don’t finish them. My mom can testify I have a room full of oil painting canvases that I started painting but never finished. 

Once I started at Facebook, I learned the motto “Done is better than Perfect.” That saved my life. Good enough is better than perfect especially in tech. 

My mentor and friend Susan Danzinger encouraged me to do an experiment: publish one post a day in the morning for a week. This sounded daunting. Once I started publishing on Medium and began amassing followers, I felt like I had to perfect my Medium posts even more to meet the high quality bar. As a result, I started to write and publish less. Like Instagram and Facebook, Medium had created a pressurized sharing environment once the quality bar kept rising. 

How do we get people to share more when they feel like their content isn’t good enough? You create safe spaces for them to share. Tumblr is my safe space. Because it doesn’t have the dopamine-drip-like-feedback loop, I am free to share what I want without worrying about not getting enough likes.  I can experiment however I want, get early feedback from blog posts on Twitter (they should really try to productize those insights for content creators), and then pick the best posts to redistribute on LinkedIn and Medium.  Coming to the end of the week, I’ve learned some things: 

1. I’m a super fast writer. I can usually bang out a blog post in 30 - 45 mins. Getting into the writing zone is the hard part. I’ve had to wake up earlier in the morning around 7am to publish something by 8am. I started every morning with coffee and Tumblr :)

2. People engage with content you write on the fly. I thought my most well-crafted blog post about online dating would be well received. Nope, it was the post about JOMO (#2) and data vs gut (#1)–both written on the fly–that got the most positive reception and engagement. People resonate with your authentic voice and less on polish, which helps me be less of a perfectionist. It’s less about the technical craft of your writing and more about the voice. 

3. Content creators are agnostic to the platform. We want to go where our readers are. The quality of the publishing tools don’t matter that much. What matters is distribution. Benedict Evans wrote about this. Tumblr follows more like a Twitter feed model in real time whereas Medium like Buzzfeed with a rebubbling model based on engagement and shares.  4. Would I do this again? Probably not. I would change the frequency and publish on a weekly basis. I found the actual writing process to not be hard but carving out the time in the morning, not working out or meditating instead to be hard. I got increasingly more fatigued by the end of the week. I think I’m going to continue trying out new blog ideas on Tumblr, find what sticks, and then repost elsewhere. My Medium has 4K followers and I have 17K followers on LinkedIn so other publishing platforms serve better for distribution. 

5. “The difference between a professional writer and an amateur writer is 45 mins a day.” This was something my neighbor Claire told me in SF.  She had worked at Penguin Publishing as an editor for a couple years. I never meant to be a writer. It’s funny how writing found me, I didn’t find it. Now I just can’t quit writing and dream of publishing my own book one day. 

This week-long experiment has been worthwhile. I found out that I’m a fast writer which is a good thing. Fast-publishing helped me overcome my web perfectionism. I just need to carve out time to write. A little writing every day builds momentum and I can feel the muscle in my brain growing stronger day by day. Thank you to all my coworkers at Tumblr who has been super supportive of my writing and dogfooding our own product! 

Best, 

–bo 

The art and science of product development 

I have worked for six tech companies by now: two in renewable energy (both Sunrun and OPower IPO’d), one in fintech (SigFig), and three in social media (Facebook, Instagram, and Tumblr). Having been in tech for six years (what feels like 20 dog years — trust me — I have aged) working across six companies in three different verticals, I start to pattern match CEOs, PMs, culture, product strategy, and companies. After a while, you realize that all companies are different but also the same. There are universal growing pains and pitfalls everywhere.

The portfolio of companies I’ve had the honor of working for ranged from Series B (<35 employees), Series C (scaling it from 100 to 300 employees), to public big tech company (>12K employees). What unites them all was the gut to data spectrum. They all fell on a axis running from pure intuition to data.

Building lasting products run the spectrum of intuition to science. No, there is no recipe for success or silver bullet. The secret sauce lies somewhere between gut and data. Going from a pure intuition model is making decisions based on your gut, user research, design-thinking, and product sense. Building products with pure science is like applying the scientific method to rigorous testing and incrementation. Neither is better or worse and they are not mutual exclusive. Where you fall on this spectrum is a function of where your PM style, company life stage, and product type.

Pure Intuition: early stage

Lifestage: pre-Series B/before product market

Product style: 0 to 1 product development

Pure intuition usually comes at the early stage companies ( pre-Series B, sub triple digit headcount). You rely on intuition where there is no clear start or direction. That intuition is usually grounded by what the founder thinks the user needs before there is a product market fit. This is where a “killer product sense” comes in. Your product sense is the internal compass that guides your through choppy waters. You end up dogfooding your own product and start talking to users on the ground. I remember taking phone calls from solar customers who were not saving after going solar and yelling at me “rip this shit off my roof!” I quantified and routed user pain points back to product and engineering and helped make product changes. Every morning, I combed through Zendesk tickets and spoke to SigFig users directly on Twitter and email to troubleshoot their portfolio manager. Staying close to the ground and listening to your users guides product development at these early stage startups.

When intuition isn’t enough, start swinging towards data

Lifestage: post product market fit, Series C+, has traction and users

Product style: How to go from v1.0 to v1.1 phase

Once you have product market fit, you need more than just data and a pulse on your users. Once your user base grows beyond a “critical mass point” e.g. 100M, like Dunbar’s number, you can’t keep track of them all. You for sure don’t know what a thirteen year old in India wants on a 2G network. This is where you need to start profiling your users by personas, conducting user research, and market analysis. Otherwise, you won’t know why a sudden drop in DAUs in India was actually from women not feeling safe using Facebook. The numbers start to capture all the nuances of an diverse user base. There is where logging becomes super important. In January 2009, Facebook’s entire growth team just dropped everything they were doing to focus on building and fixing logging. When growth slowed down in March of 2009, they were able to tease apart the nuanced variables at play through reviewing the data they logged.

When you rely too much on data and not enough intuition: large tech company

Product style: Iterating from v7.0 to 7.1

As much as I believe that data wins arguments, when you defer to data as the sole source of truth, you start to loose the nuances that comes from intuition. I call this “sciencing the shit out of products”. At Facebook, you moved numbers as a PM. No product would ever ship until you have gone through rigorous A/B testing yielding statistically significant result. You would never release a redesign that would tank metrics. Like chemical titration, you slowly tested and turned the knobs until you perfected the right balance of numbers. This process, albeit effective, stymies a lot of innovation. Just look at the recent strategy of Facebook stories. Do you really need stories in three different places??

I’m wary of “sciencing the shit” out of tech because it removes the humanity. You start to dehumanize whatever you’re building without focusing on the people problems. At the same time, I’m wary of blindly following our intuition too much without questioning our assumptions for what’s “right”. It all comes down to a balance and there is no recipe for success.

“It is in Apple’s DNA that technology alone is not enough — it’s technology married with liberal arts, married with the humanities, that yields us the results that make our heart sing.” — Steve Jobs

If you balance your gut intuition with data, you’ll be able to build products that make your heart sing. Don’t over index on either end of the gut vs data spectrum. Know when to follow your gut, and don’t forget to trust and verify with numbers.

Follow your heart and validate with numbers, 

--bo 

When I moved from SF to NYC I decided to KonMari all my possessions. I fell in love Marie Kondo's book the The Life Changing Magic of Tidying Up. Through Marie Kondo's methods I got rid of half my things and arrived to NYC with two suitcases and boxes. Through the KonMari Method, I realized that I loved to collect chachkies and hung onto sentimental items past their shelf life. I gave away dresses to friends who could wear them better than me. I gave away skincare and makeup I had hoarded. At my going away party I had a box of “free shit” including books, espresso machine, and Facebook Analog lab posters. The process of letting go, donating, and organizing my things felt therapeutic and symbolic of my period in SF coming to a close. Add constraints to your app. See your app in #s.  We can also apply the KonMari method to the products we build as well. Recently, our CEO tasked me with auditing and inventorizing our product limitations. One of our core values at Tumblr is “Limitless Expression”. As a result, our app is also pretty limitless in the sense we don't set a lot of constraints for what you can do. Exploring the technical limitations of how many videos you can upload per post, how many tags you can add, how many inline links you can embed made me see Tumblr in #s. Seeing your app in #s can be a great way to think about what constraints you have and need to establish. A bloated app creates innovator's dilemma Oftentimes we mistake more features as better. When I was working at Facebook, the app had become bloated with four tabs and multiple drawers. There was a lot of internal competition for which team could test on which tab. You couldn't launch a feature if you took down another team's metrics, which makes sense, but also caused a lot of barrier to innovation. New products were often stymied by the many opposing forces (real estate, metrics interactions) in a cluttered app. A bloated app like your sock drawer prevents you from getting your shit in order or make room for anything new. Instead of fighting for precious real estate, I think we as PMs could have thought about what can we remove to simplify the app and create more white space for innovation. 

Have negative space in your app means you have the freedom to not design within boundaries or limited by visual hierarchy. Creating negative space means you can roam freely and experiment things you otherwise would not have tried. 

New York City is a place of FOMO (fear of missing out). After moving to NY, I quickly became overwhelmed by the amount of stimuli, events, places, and new people. I faced too much input and not enough time to process everything. The magnitude of options in this city fueled my FOMO. FOMO is what drives people to say “YES” to every invite enthusiastically, schedule back to back events, and burn themselves out. FOMO tells you that whatever you are doing right now is certainly inferior to what others are doing. It’s the typical comparing with the Joneses x upward comparison. 

Working in technology doesn’t help with my FOMO either. My job is constantly playing catch up on the latest tech trends and launches. Fueled by FOMO, I need to constantly be in the know about the latest tech news and competitive market analysis. I want to be in three different Slack conversations at once for fear of missing out crucial conversations. Working in social media, I am also responsible for building technology that causes FOMO. Both the victim and perpetrator, FOMO seeps into every crevice of my life.

FOMO comes from a horizontal slice of everything 

For the first time in society, social media allows us to make a horizontal slice at any point in time and cross-reference what other people are doing. Instagram stories, Snapchat stories, live-streaming, and Facebook enable us to take a cross-section of our lives and compare with others. How can you be possibly happy when you see other people doing more exciting and awesome things? Therein lies the modern day conundrum of social media.

When I first moved to NYC, I made myself write down the following intentions for the first 6 months of JOMO (joy of missing out) lifestyle:

Practice essentialism. Say “No” to people more often especially the type who will energetically drain you. Say “Yes” to people who follow through and are positive and uplifting. Ruthlessly prune out people who don't add any value to your life.

Go out 3Xs max a week. Make sure to recharge with down time to deep think, write, and do nothing, puttering around your apartment. Sleep 7 - 8 hrs a night. Workout 3Xs a week. Meditate and journal daily.

Establish normalcy and routine — find your go to coffee shop, yoga studio, pilates studio etc.

I knew that if I didn't establish the JOMO lifestyle, I would go off the deep end, going out every night, and burning the midnight oil until I burned myself out. Without guard rails and routine, FOMO would ruin New York for me. 

I encountered JOMO in an Huffington Post article in 2014 but it took me 3 years to finally internalize it. JOMO is very contrary to my nature. I'm the type of person who walks into a room and soaks up the surrounding energy. I have this uncanny ability to take everyone's temperature in a room and perceive how others are feeling. I'm your textbook empath. This need to know how other people are doing/feeling fuels my addiction to social media.

JOMO on the other hand, tells me to disconnect, put my phone on airplane mode, and take a bath in that order. JOMO is what helped me recharge on a Friday night with a book, candle burning, face mask, in the tub, listening to a sick playlist. If it weren't for JOMO, I don't think I could have survived New York.

Is your product building JOMO? 

JOMO is a mindset I apply to the products I build too. What is the *one thing* we can deliver to you that is adding tangible value instead of perceived value? How can we create a feedback loop without pulling the human levers of FOMO and the addictive dopamine drip from more likes? How can we give you less so you walk away with more--satiated? How can I avoid tapping into FOMO to increase time spent on an app? At the end of the day, I don’t want to build products that collectively lower humanity’s happiness. 

Unlike FOMO, JOMO makes us feel like we are ENOUGH. I don't need to RSVP to the 20 events I get invited to a week. Neither to I have to say “YES” to every coffee meeting invite. JOMO forces me to be more selective of who I spend time with. JOMO tells me I don't need to see every visitor who is passing through town or offer free product advice to friends and acquaintances out of obligation. JOMO allows me to simply be “Bo” in my truest essence and nothing more.

I hope you give JOMO a try because soon you'll realize that FOMO is so overrated and passé. And perhaps in 2017, you’ll join me making JOMO the lifestyle we all aspire to.

JOMO ✌️,

--bo

I had a weird interaction recently. I went on a business meeting that turned into  a three hour date.  I had been beta-testing a dating app and video chatting with the founder for the last few weeks. He was based in SF while I was in NYC. He asked to meet up when I jokingly offered to be a NYC ambassador for him so I could match with more people in NYC. What ensued was a very ambiguous meeting where a coffee meeting turned into a three hour walk through Manhattan Ethan-Hawke-Julie-Delpy-Before-Sunset style. After that meeting I decided to not do anything contrary to my inclination to text and say “I had a great time! Would love to meet up next time I'm in SF.” Something about the nebulous circumstances of me giving him free product advice and us living in different cities gave me pause. I decided to wait for him to show any indication of interest instead. As someone who writes openly about my weird online to offline interactions and social experiments,  I have always been a huge advocate of radical honesty, vulnerability, and authenticity on the internet but find it incredibly hard to be vulnerable when it comes to dating. This caused quite a bit of cognitive dissonance.

I wonder if the interplay of technology and dating has made us less vulnerable? Has humankind become more jaded, skeptical, dehumanized because of the myriad of online dating apps available?

Is the lack of vulnerability stemming from technology or humans? I don't know where the human problem starts and the tech problem stops.

The internet has introduced new social norms creating an intricate web of etiquette and power play. 

I can't help but wonder if we have all become stymied in digital complexity, paradox of choices, perceived plentifulness, and maximizing mentality. I wonder if modern romance, inevitably intertwined with online dating, is dehumanizing but altogether not that different from offline dating.

According to Marshall McCluhan all technology is an extension of man. Technology will sharpen whatever instincts we have and further any human nature including our innate need for love. Following McCluhan's philosophy, I can't demonize online dating apps because it is an extension of human nature. I can rage quit online dating at the height of my disillusionment and frustration--deleting all my dating apps one Sunday morning--but I can't rage quit the pursuit of love altogether. Instead of fighting technology, we can recognize our resulting biases and cognitive distortions:

Maximizing Mentality - It's easy to think that there's always something better out there when you have an endless rolodex of cards to swipe through. The swipe interface is one of the most dehumanizing ways of commoditizing people. The stacked UI of multiple cards on Tinder creates the illusion of plenty. However, your ratio for compatibility doesn't change. Quantity ≠ quality unfortunately. More is not more, sometimes even less.  

Lack of Vulnerability - Thanks to the advent of the internet, dating has turned into an arms race or blood sport of sorts. Many of my friends lament how tricky is to be real and genuine with other people who are playing games. The “game” of not showing vulnerability. Vulnerability is a rare currency. There is a clear winner and loser where the first person who texts back, shows their genuine emotions, and signals they care to the other person loses. By showing your hand early you risk scaring the other person off. If you're too ambivalent you risk putting off someone who actually likes you. It's a zero sum game. Some people strictly abide by a no double text game and try to not use full sentences or emojis; I cry for the future of the English language. The rise of terms like “cushioning” and “breadcrumbing” explain how people can simultaneously juggle multiple people as backups without investing in one person because it's too risky. Putting your eggs across many baskets is hedging in game theory.

Paradox of Choices - It's easy to constantly cross compare different people when there are so many options at your disposal. Why just text one person when you can text five people? Positive psychology shows that our maximizing mentality will not lead to happiness but rather disillusionment and a constant search for “more” in every aspect of our lives a.k.a. “Hedonic Treadmill”. Fulfillment lies in the “enough”. We just have to define it for ourselves.  Perhaps it's not about more choices but less and satisficing when you come across someone pretty great.

Maybe we become jaded and less vulnerable because of the sheer number of people accessible to us but unlike endless swipes, our heart cannot withstand endless heartbreaks. It's up to us to define what is enough for us when we're overcome with the paradox of choices and maximizing mindset. I hope that if we recognize these maximizing tendencies, text games, and paradox of choices we’ll be better equipped to follow our hearts instead of be a slave to the infinite swipes.

Like all things in life, dating is nuanced and there is no set rulebook. As much as I want to analyze everything (trust me, I do and it sucks) there is no black or white way to date. Sometimes you can't be readily vulnerable or genuine because you have been hurt too many times and that's ok. My heart is still healing and it will take time for me to be openly vulnerable again. Sometimes you have to hedge your bets and just observe how things play out and that's ok. Sometimes you just delete all your dating apps and take a break from it all. Whichever avenue you choose, don't forget that like all matters of the heart you'll know it when you find it, just don't maximize to obscurity.

Yours truly,