Prototype Year

For this Tool Sharing Tuesday, I’d love to share one of the most powerful social tools of them all –– a powerful, human introduction. This post was originally featured on the Experience Institute blog (which you should probably check out.)

This year has had no shortage of new hellos.

I’ve done it all: cold emails, requested introductions, brokered new friendships, and been on the receiving end of serious professional generosity. And with each small act of connection, I’ve relearned the importance of a powerful, and personal, introduction.

I’m reminded of an experience from a few years ago. A close friend made a quick, generic introduction to somebody whose advice I was seeking. The intro was, well, flat and bland. Nothing like our robust friendship. Unsurprisingly, the only reply I heard back was the sound of crickets…and my own disappointment.

A year and a half later, another mutual friend invited me and that same person–the one who I’d hoped to meet via email–to drinks. This time, the connection was immediate. Now when we’re in the same city, we make time to grab a meal and catch up.

I don’t want to blame the flat email for our delayed personal and professional friendship. Inboxes are constantly in triage mode. People are obnoxiously busy. But every so often, I reflect on how hasty introductions like that first one not only make me feel (okay, so my ego might have been bruised) but how they can actually hinder a relationship from developing at all despite good intentions.

This experience reignited my commitment to making thoughtful introductions. And this year, I’ve been on the giving and receiving end of many. Recently, I actually received separate thank you notes and follow ups about the way I introduced two people. These routine emails had impact. I learned that the information shared and tone of an intro can fuel richer conversation, spark subsequent collaboration, and help independent relationships form more quickly. These connections worked because both parties felt like people to each other. And that’s what mattered.

As someone who loves to host dinner parties, my approach to digitally connecting people is not dissimilar. While writing this, I read a great piece that echoed the sentiment of using a hosting mindset online:

“The better we become at introductions, the better we become at seeing hidden connections between people who could hit it off….When making email introductions, you are the host. People deserve the same amount of hospitality you would give your dinner guests.”

These introductory emails come naturally to me now. It’s an honor to celebrate and connect two people who might find mutual benefit. When I look back at past emails, I notice that I’m subconsciously answering certain questions. Why must these people meet? Why do I think these people rock? Why might somebody else? How will these people find mutual benefit… and more importantly, mutual connection?

Here’s a quick cheat sheet of questions to ask yourself as you are crafting thoughtful introductions:

What is this purpose of the introduction? (Most people usually stop here.)

What are meaningful, or mutual, affiliations? (…or they stop here.)

In what context are you connected to each person?

What’s a conversation you’d think these people would love to have?

What information would connect them on a personal level? (shared hobby, passion, etc)

What’s a milestone, brag, or recent highlight of their personal or professional life? (a new baby, a promotion, a published article…)

What makes this person special to you personally?

What unique skills, superpowers, traits, or dispositions does each person have?

There’s much more to say on this topic whether it’s being confident in your introductions, choosing the right approach to making connections, or asking for an intro. But at the heart of it lies a simple message:

Maybe it’s just my love of the underdog, but I think it’s about time we show some love to the index card. The older, adhesive-less grandfather to the fashionable sticky note is too often forgotten. Whereas the sticky note is a metaphor for innovation, the index card represents a tradition of staid organization. It’s true, I’ve been guilty of a blind love 3M’s colorful collaboration gems, and I’m not alone in my sticky-note adoration (eg. an artistic ode, a loving competition, a self-referential love).

I want to share how I rekindled my love for the index card. But first, let’s explore how others have built their lives around these plain vanilla tools of the office supply world.

Some memories of index cards are universal experiences. If you were born before 1990, you may remember your favorite school librarian fastidiously organizing the card catalogue. Similarly, you may have written your first report or doctoral thesis on these little guys (and you might still be bitter about it). Index cards were there for us growing up, from learning a language to studying for tests to following your first secret family recipe.

Moreover, they’ve fueled (and continue to fuel) some of our favorite creatives and business leaders:

The late Joan Rivers was known for her persistent and prolific career as a comedienne. The method behind the madness? Over a million index cards of jokes, filed and sorted in her Upper East Side apartment. She’s said this collection represents the “social history of the United States.

Writer and teacher, Anne Lamott, takes a less precise, but no less committed, approach. "I have index cards and pens all over the house—by the bed, in the bathroom, in the kitchen, by the phones, and I have them in the glove compartment of my car. I carry one with me in my back pocket when I take my dog for a walk. In fact, I carry it folded lengthwise, if you need to know, so that, God forbid, I won’t look bulky. You may want to consider doing the same." She later uses these snippets to flesh out stories and essays, if even just a detail: "Sometimes, if I overhear or think of an exact line of dialogue or a transition, I write it down verbatim."

Creative doodler and artistic instigator, Austin Kleon is famous for making his work public. His battle cry is “Show Your Work!” (he’s even written a book about it). Austin does an incredible job giving glimpse into his everyday process and takes great care to celebrate others’ practices as well. Especially those that involve the ubiquitous card. Fun Fact: His first book was conceived on index cards and he even shared the “deleted scenes” with readers.

Writer and broadcaster, Merlin Mann, built on the list-based “Getting Things Done" system of David Allen by creating and evangelizing the Hipster PDA. The Hipster PDA is an index-card-and-binder-clip-based productivity hack. Merlin Mann keeps a wiki that catalogues writers who use index cards– how’s that for fandom?

The index card is alive and well in the creative world and has a distinct longevity in addition to its modularity. A durability I needed in my life. Recently, I ordered 1,000 to supplement my sticky addiction. Immediately, I found two favorite uses:

The Notebook Hack: Taking another cue from librarians, I ordered a set of  manila card pockets and stuck them into my favorite planner and Moleskine notebook. They were the perfect size, holding about 15 index cards and a few business cards to boot. While I don’t have a science to my madness yet, these in-a-pinch index cards make excellent to-do lists, idea repositories, or covert jotting pads. (It helps that I keep tape in my pencil case to paste these little guys in my notebook when needed.)

The Daily Provocation: This year I am teaching my first official college class. In an attempt to slowly learn more about my students (and actually take attendance), I start each class with a personal prompt about the day’s topic. And yes, sometimes I make them draw. Every week, I get to know more about my students, and it pushes my co-instructor and me to root our classes in relevance and relationships. (H/T to accidental creativity professor Lynda Barry who takes class attendance with 2-minute self portraits on index cards.)

While the sticky note goes digital, gets cozy with Evernote, and is praised for its collaborative qualities ––– there’s no shortage of reasons to love the traditional index card. What’s yours?

"The experiences we place ourselves in often beg for great questions, not great answers. They demand curiosity, not expertise….[they] are rooted in a particular mindset”

– Zak Tracy, Experience Institute blog

As my friend and Experience Institute colleague ponders the nature of asking great questions in this week’s blog, I’m reminded of the next challenge of inquiry –– living in it. You may be able to articulate questions that color your life, relationship, or community –– but finding a graceful way to embrace them is a challenge unto itself. 

As I navigate relationships, careers, and commitments, I often experience a distinct uneasiness. This discomfort is the challenge of exploring one’s own questions. The fear of uncertainty in the face of inquiry. However, there is one passage that seems to calm me in these hazy moments. From Rilke’s Letters to a Young Poet*:

"I beg you, to have patience with everything unresolved in your heart and to try to love the questions themselves as if they were locked rooms or books written in a very foreign language. Don’t search for the answers, which could not be given to you now, because you would not be able to live them. And the point is to live everything. Live the questions now. Perhaps then, someday far in the future, you will gradually, without even noticing it, live your way into the answer." 

Since I was 17, I’ve had Rilke’s meditation hanging above my bed. It gently reminds me to greet questions in my life with patience rather than torment. It’s still a struggle to live up to its call, but a worthy one.

"What questions are you trying to love and live into right now?"

#expquestions

*Letters to a Young poet is a collection of the correspondence between Rainer Maria Rilke and 19-year-old Franz Xaver Kappus from 1902-1908. Kappus implored Rilke for poetic, career, and life advice. Though they never met, Rilke’s beautiful letters contain gems of insight to guide any life. 

Sometimes it’s the simple tools used in new ways that are the most powerful. 

I’ve recently rekindled my love with Google forms. Simple. Timeless. Endlessly customizable. From party planning to community surveys to organizing farm shares –– they’ve been there for me since the beginning. However, as my need for organizing or analytics has gotten more complex, I’ve slowly swapped Google forms for more professional, robust alternatives*.

But, somehow, Google forms remains relevant...Especially since I started capturing my personal meeting notes with a simple google forms hack. 

My challenge: I’m constantly meeting with incredible people and organizations. Beyond being the building blocks of new relationships, these meetings are filled with learning opportunities –– chock full of insights, ahas, and advice. They also have these wonderful mutual moments of support –– “You must meet…” “I’ll send you that…” “This should be on your bookshelf…” It doesn’t always make sense to pull out a pen and paper mid-meeting to capture. But it’s always nice to leave these coffee-fueled brain-melds with concrete reflections and actions.

My solution: The Coffee Log. A simple google form set as a home button on my iPhone and web browser. After an enriching personal meeting, I spend a minute using the form to capture insights. These generally fall in a few categories: relevant work/life updates, sticky concepts, recommended media, recommended connections, and advice. It’s as easy as writing a few text messages, but they are stored in a central place that you can then reference for your own knowledge or follow-up. 

The inspiration:  I generally have a good people memory, but I needed something more. After a lost-notebook and too many blank out moments when trying to remember ephemeral conversation moments –– I knew I needed a solution.

One particularly motivating article was Robyn Scott’s Medium post, The 30 second habit with a lifelong impact. In it, she describes the simple advice she learned from a successful friend’s grandfather:

"There are no quick fixes...I write it only having become convinced, after several months of experimentation, that one of the simplest pieces of advice I’ve heard is also one of the best...Immediately after every lecture, meeting, or any significant experience, take 30 seconds — no more, no less — to write down the most important points. If you always do just this, said his grandfather, and even if you only do this, with no other revision, you will be okay.”

  She extrapolates on the magic that lies in this habit. The three points that stick out to me are:

"Detail is a trap” - I find I like using this handy tool best on mobile. Why? I am forced to write less. An online survey is too daunting and I end up nearly transcribing my recollections. Done is better than perfect.

"You’re able to help others more” - Absolutely. After a few weeks, I added a "follow-up" field that allows me to distinguish the most actionable follow up. I find that I’m following up more actionably –– from asks to facilitating introductions.

"You’re able to listen better, and ask better questions” - Conversations need to marinate. I find that it is easier for me to ask more thoughtful questions in subsequent interactions when I jot down the “aha” moments of a conversation

How will you hack simple tools to make your life easier and relationships stronger this year?

As the holidays approach, I often sense that our collective pulse quickens. Our minds clutter as we balance the tasks and emotions of this rushed season of personal resolution, social connection, and professional obligation. We're on the precipice of chaos, albeit of the generally cheerful variety. It's in this moment that I’m reminded of our opportunity to imbue the season with a sense of intentionality and centeredness. 

Now, before we begin, let’s both take a deep breath in… and out.  For this Tool-Sharing Tuesday, I’m sharing some of the digital tools that have brought mindfulness into my day. In full disclosure, I’m a newbie at this. But the simple act of quiet, breath, and presence has done wonders for me. As designing a more intentional lifestyle is a theme of my year, I’d love to share my adventures.  If you are wondering ’should I meditate?'––the answer is yes.  I’m not saying you need to visit your local Buddhist temple on the regular or even get comfortable with the idea of yoga pants. Mindfulness spans boundaries of culture, lifestyle, and demographic. There is a ton of research on the power of mindfulness and a regular practice of meditation, like this great overview at Berkeley’s Greater Good Science Center. From harnessing attention to regulating emotion to enhancing creativity, meditation is a powerful force for good. In our world of devices, divided attention, and fleeting connections, I'm drawn to the emerging development of mindfulness programs in school and work environments. They’ve shown effectiveness in mitigating childhood stress and college stress alike, while also increasing character traits such as compassion. Talk about bang for your buck.  Personally, I began mini-meditation sessions after becoming fed up with my own fractured sense of focus. Switching tabs and programs all day made me feel disembodied and my brain shallow. I also wanted to sooth my tight muscles and ease my finicky mood. Strangely, it was the same digital tool I sought detachment from that powers many of my meditative moments. 

Calm I like this app for its simple interface and ability to choose guided or unguided timed meditations with ambient noise. For beginners, it has a set of introductory sessions that walk you through the main aspects of meditation. It also has additional themed mediations that you can unlock in the program. My only wish is that it had a more elegant tracking mechanism to better prompt habit building that evolves into practice. Oh yeah, it’s free. Headspace Headspace is downright lovely and slightly cheeky. Simple, clean interface. Beautiful animations. A pleasant man with a lightly British accent guides you through your sessions –– which is always nice. Plus, it integrates reminders, tracking, and gives you the ability to invite friends. The catch is, after a lovely 10 session intro, you have to pay a monthly fee for use. $8 a month is less than two soy lattes, but isn’t nothing. My thought? Ditch Netflix for a year and give it a try. Here’s a pretty in-depth review here.  I’ve also heard Enso is great for those who prefer unguided meditation. With an elegant interface, it helps you focus on building a habit of quiet in your life–– framing it with a simple bell. 

If you want to diversify and go deeper, there are other virtual alternatives. (Mind you, there is power in participating in an in-person class as well). One alternative to finding a studio to practice in is to find a podcast that resonates with you. Maria Popova, the ever-generous curator behind the brilliant BrainPickings, was on the Tim Ferris podcast recently and shared her favorite mediation teacher. Tara Brach posts a weekly(isn) guided meditation that accompanies each of her lectures. I found her presence both calming and accessible with a palpable compassion. Try starting with the Smile mediation (excuse the background noise, it's recorded live).

Do you practice any forms of meditation or mindfulness? Are there tools or routines that help guide and ground you?

Images: Recently my Ei comrades have been organizing weekly yoga and mindfulness sessions in the west loop at Open Secret Studios. Even with the change of seasons, it's filled with incredible light.

Gap year? Leap year? Sabbatical? A very busy break?

When people asked, “What are you doing this year?” I didn’t quite know what to say.

I went through a phase where I referred to it as my learning sabbatical, but that didn’t quite fit. Sabbatical shares a root with the Hebrew term “shabbat or Sabbath” which literally means a “ceasing.” This year wasn’t about rest. A “gap year” harkened to those exploratory breaks associated with the bridge from high school to college or college to the real world.

For the mid-career set, there aren’t really terms, nor social acceptance, for a pause in one’s career and education. People pivot and become “career switchers.” Many use grad school to catch their breath, and deepen their debt load.  The intrepid may store up financial reserves and take extended breaks to travel, dabble, or serve. But often these decisions are met with glares and confusion by colleagues, family, and mentors.

After trying to explain Experience Institute and my own journey many times over, I blurted out in conversation:

“It’s like…a prototype year.”

It stuck. After reflecting and unpacking my background in design and learning, I became more convinced of the magic in “prototype year.” What does it mean exactly?

Unpacking prototypes: Primitive forms and iterative processes

First of all, prototype means many things to many people — especially the design and engineering set. It’s derived from Greek (πρωτότυπον) — protos (“first, primitive, original”) and typos (“impression, mold, pattern, form”). Most are familiar with its engineering definition, simply stated by Bill Moggridge as “a representation of a design, made before the final solution exists.” These primitive forms test variables that a team is refining and can be expressed in a range of fidelity and mediums.

image source

However, as a process-based term, “prototyping” takes on new depths. Prototypes can be used early in a process to gain empathy and solicit insight from users. They can be used in brainstorming and conceptualization to demonstrate and “think aloud” with a team or client. And, of course, they are used later as a model to understand form and contextual use. Whether empathetic or exploratory, demonstrative or experiential, high fidelity or improvisatory — the act of prototyping is empowering.

My prototype year is all of these things. It is about empowerment and new experiences, insight and iteration — but on a personal level.

So what does prototyping learning experiences look like?

Design is a learning process, and learning can be a designed process

This intuitive blurting out of “prototype year” meant more than I originally thought. With a background of learning sciences and design research, it just fit.

The most powerful element for me is the idea of intentional experimentation. Rather than a checklist approach outlining endless goals, I had to be comfortable articulating and testing my personal assumptions and questions.

I’ve found that outlining rich questions and assumptions biases me towards experimentation and reflection in a unique way. These hypotheses help me explore the nuances of work — the settings, skills, and subjects — I want to test. For example, I love creative facilitation and design strategy for social clients. What do these skills look like in a venture capital setting? Working intrapreneurially in a global corporation has been enriching, but what does this look like in an entrepreneurial context?

Pause and Prototype: The first step is the hardest

As I define each area of my career I want to test, I feel more empowered. Prototyping is the fun, albeit messy, part. It’s the pause that’s challenging.

However uncomfortable, creating liminal space in our lives in which to explore, learn, and reflect is important. To have a “learning society“, we need to not only make more of these moments for ourselves, but encourage reflection and experimentation in others — long after the textbooks close. While I’m taking a year to experiment, these learning leaps don’t have to be dauntingly time intensive. How can you create moments to pause and prototype in your everyday?

Originally posted on the Experience Institute blog:

References: An evolving collection of references supported this working blog entry. Check out more of the links below from thinkers such as Donald Schön, David Kolb, Liz Gerber, and Björn Hartmann.

http://www.etymonline.com/

http://www.smashingmagazine.com/2014/10/06/the-skeptics-guide-to-low-fidelity-prototyping/

http://infed.org/mobi/david-a-kolb-on-experiential-learning/

http://www.simplypsychology.org/learning-kolb.html

http://infed.org/mobi/donald-schon-learning-reflection-change/

http://egerber.mech.northwestern.edu/wp-content/uploads/2012/11/Gerber_PsychologicalExperienceofPrototyping.pdf

I’m fascinated by the way people work. 

The actual what, how, and where of it all. Yes, I love hearing people’s macro mindsets and strategies, but sometimes it’s the tactical that excites me. Our conversations about work are often too abstract. There's something refreshingly tangible about prying open your creative colleagues’ bags of tricks. I find myself asking people about the tools that have impacted their lives...or that they just plain geek out about. I'm always trying to discover:

How do busy people use tools authentically to cultivate, strengthen, and maintain relationships? 

How do creatives build workflows that work for them and their teams?

What’s your everyday carry of necessities? Your digital toolbox?

While I have always tended toward analog tools, my twin brother’s digital tinkering has rubbed off on me slightly. Matt, prone to deep research and the occasional hyperbole, has been known to gleefully exclaim: “that just changed my life!” when he discovers a particularly helpful keyboard shortcut. His enthusiasm for finding, using, and sharing the tools that delight him is something I’ve always admired. The fact that he is the director of development for a growing startup gives him a significant edge in the digital tool arena. 

Another inspiration for unpacking workflows is Tim Ferriss. Recently, I’ve added Tim Ferriss’s podcast to my weekly listening. Ferris, of The 4-Hour Workweek fame, is masterful at deconstructing world-class performers. His ability to find the inspirational and tactical alike in his interviews is a refreshing and practical addition to my podcast consumption.

This year for me is about honing the art of the day to day–– whether that's revisiting personal practices, using new tools, or refreshing habits. That’s why every(ish) Tuesday, I’ll share a tool or practice that has me jazzed lately.

What tool has delighted you or made your life easier lately?

  It's easy to get sucked into the landless timewarp that is the internet. With each successive click and tab opened, we become more disembodied and ungrounded. 

Until now...

Every once in a while, you find a tool that is a breath of fresh air. Earth view from Google Maps gives you mini-aerial glimpses of planet earth every time you open a new browser tab. Filled with hypnotizing patterns, varied textures, and deep colors –– you often find yourself mistaking the images for works of art or alien planets. But, they are right here on earth. Mind blown.

These micro moments of awe inspire the same wanderlust as the annual release of NYTimes' "Places to go in ____" or the mesmerizing coffee table book Earth from Above... Except you get these doses of appreciation daily.

It falls under the category of tools that delight.... but I must say, my well-being has definitely increased since my days have been punctuated with earthly wonder. 

The internet is so useful it’s paralyzing. 

With our abundance of platforms, the act of managing all of our worlds can become a full time job. One tool that perpetually and discreetly delights is IFTTT –– if this, then that. It’s really that simple. It’s a rad tool to make all your platforms play nice in your personal digital sandbox.

Identify your goals. While your recipes will be specific, your goals might be more general. "I want to keep the pulse of the latest business trends. I want to manage my side hustle virtually. I want to feel more prepared every day.” Because there are a million recipes to achieve these goals, it is important to keep focused on your human purpose.

Audit your platforms and habits. People feel more comfortable with certain platforms, experiences, and feature sets. What applications do you like best for reading? On which social media platforms are you most consistent (and sane!)? What manual micro-processes do you often repeat (backing up pictures, searching for content, cross listing)?

Get inspired. Think logically. Build your recipes. Once you identify a few snags to fix or processes to automate, It’s time to cook. If you need help getting started, try checking out the popular recipes, recipes by “channel,” or curated collections  Think of it as elementary programming with simple graphic madlibs. 

Set and forget. Once your set, all you have to do is enjoy your newfound efficiency. It’s a great way to add more intentionality into your digital life (and organization too). 

Taming the email beast seems to be the constant battle we’re all facing. Whether inbox zero or priority inbox, time boxing or linking to tasks –– it’s a war with many fronts.

There are two weapons that have been helping me in the never-ending content combat.

With a flexible schedule, part of my challenge is reducing the email traffic related to logistics. For this, my new savior has been Assistant.to. This simple Google Chrome extension eliminates the back and forth of scheduling meetings. It allows the “scheduler” to identify what works in their calendar and propose these times to their partner. The theory is, with three days and multiple windows identified, your partner will likely find a slot that works. With a click of a button, the meeting is booked and in both of your calendars. 

Now, I feel a little sheepish when I am using it in contexts that blur the personal and professional realms. I often find myself mildly caveating the use of a tool rather than going casual: "Here's a fun little tool I've been trying, let's see if it works to get a time in the books!” However, most folks love the ease so much they don’t mind. An exchange:

"What a handy platform...Happily booked us a time!” "I know, I love it. Always wonder if it comes off awkward/overly formal to the other party... but it is just so darn easy!" "My impression was wow - are they ever organized/busy :)"

I’ll take the impression. My life has been easier since Assistant.to came into it. Even if the organization comment is a bit overstated.

The other favorite in the bunch is Boomerang. This other Chrome plug-in solves two worthy problems:

The “I wrote a bunch of important emails at 2:00am on Saturday and wish I could schedule them for 7:00am Monday” challenge

— and—

The “I need to remember to email this person back if they don’t respond….oh no, help, I’m drowning in emails” challenge

With a simple button you can schedule the sending of emails and also schedule emails to “boomerang” back into your inbox after a set amount of time.

Sanity gained. Time saved. The war of email just got that much more peaceful.

What helps you manage your Gmail account?

Download Boomerang or Assistant.to in the Chrome Web Store.

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