Picking the Habit:
One of the critical first requirements to developing habits is to pick one and pick only one at any given moment. If I remember one thing from Charles Duhigg’s Power of Habit, it’s that the best way to develop no new habits is to try and develop a million new habits. 

This is a beautiful limitation. For overachieving, Ivy grad, people pleasers like myself, the economizing of habit formation begets a precise prioritization of what matters most. I struggle with this. After my friend let me know about his Habit Lab, I spent this past week thinking of habits I wanted to explore and improve:

• decrease my phone usage
• increase the number of books read each month
• eat less on the go/prepare meals more frequently each week
• create more down time
• meet and engage with acquaintances more

The truth is that my general theme for 2017 is paradoxical to the themes of productivity, life hacking, and output. Why? Because over the past year I’ve recognized that for me, much like a spotlight in a dark room, I only have the ability to shed light on a specific area of focus at any given time. Energy spent on production and output has created for me plenty of extra time. What I haven’t focused on is using that surplus of time to self reflect and increase my self awareness. In other words, I am much more quickly able to add on to my plate rather than recognize when my plate is full. This has ultimately led to a feeling as if my world is one of scarcity rather than abundance.

So I’ve decided to re-develop my meditation practice. My initial goal will be to meditate once daily. At my peak following my ten day silent Vipassana retreat I was able to sustain an hour long sit each day, sometimes twice a day. I now often find myself skipping days or even weeks without sitting for even ten minutes. 

By developing a better meditation practice, I’ll (hopefully) also better enable myself to endure periods of long focus. In other words, by focusing on a sustainable consistent meditation practice, I’ll enable myself to more easily decrease phone usage and stay focused when reading books. Fringe benefits :)

Engineering the Habit:
Duhigg is a big proponent of using cues to engineer behavior (fig 1).

For this reason, I love listening to the same playlist when I walk into the gym before what I know will be a difficult training session. In similar fashion, when I think about some of the reasons why I’ve fallen off my meditation habit I recognize that my frequent trips for work to Seattle, San Francisco, and New York have interrupted a morning ritual that was rooted in a process that started in my own home, after first drinking a glass of water in my own kitchen. Preparing and hand pouring my first cup of coffee, staring out the window for the first minutes of the day, and making breakfast primed myself for my meditation session. In 2016 there were just four weeks out of the year where I didn’t find myself on an airplane. Just me and my good friend Delta chumming it up. Waking up in a hotel or an AirBnB changed that ritual and priming process for my meditation and slowly over time I lost my habit and practice. 

I believe this is where I faltered in the past. Because of my changing environments, I feel the need to create two cues for a meditation practice: one for the home, and one for the road. 

At home:
I wish I was so good that I could say I maintained a consistent practice for the weeks I spend at home. But I’d be lying if I did. The good news is that because I’ve engineered a meditation habit for my life at home, I can use the same cue, routine, and reward as I did before:

Cue: Immediately following my morning cup of coffee, I’ll spend twenty minutes (twenty minutes to start, I’ll play around with the length of the sit eventually) sitting on my meditation cushion.

Routine: I tend not to use my phone until after I’ve had my cup of coffee. Once I do, I’ll use the Insight Meditation timer app to accompany my twenty minutes of meditation. Directly next to my bed I have a meditation cushion and a blanket. I’m always freezing cold in the morning so as part of my routine I’ll sit down on the cushion and drape the blanket over the front of my shoulders. The Insight Meditation timer app begins with a bell (another cue) and I meditate. 

Reward: I don’t know if this is cheating, but I genuinely feel clear and safe after a twenty minute meditation. That is the reward. I don’t plan on including any other external reward with this habit. When 99% of my day is spent fielding calls or attending meetings or performing in some variation for another person, I truly enjoy the feeling after twenty minutes of indulgence in my silence. 

On the road: 
When I am traveling I usually stay at hotels. Most hotels have a surplus of pillows for one person. In fact, often times when in a hotel room I say to myself with the flow of Kanye: no one man should have all these pillows. But no more! 

Cue: I won’t have a cup of coffee to prepare in the kitchen. But I will use a glass of cold water to prime myself. I also plan to place two pillows in the corner upon first checking into the room. This mimics the meditation cushion in my bedroom and by placing the pillows there the night before I failproof myself from cheating that step the next morning. 

Routine: I intend to employ the same routine as home, using the Insight Meditation app to guide me through my meditation. My specific meditation practice is Vipassana which emphasizes a focus on the breath and body awareness. Good news: whether I am at home or on the road, my breath stays with me. So long as that doesn’t change, neither will the actual meditation routine. 

Reward: Contrary to my on the road meditation routine, this will change. Because I haven’t had a cup of coffee, I plan on rewarding my on the road meditation practice with my cup of coffee immediately after my meditation. This will usually result in a saunter down to the nearby Starbucks before I go about my day. All of this, of course, comes in addition to the reward of clear headedness that accompanies any meditation sit.

Results:
Well…I don’t have any of these yet. I am at day zero. Over the course of the few weeks I aim to use this site to document my experience. What were the unexpected barriers? Did I adjust to get around those barriers? Or did I utterly fail? Aside from accountability, I think this will help me learn how habits are either won or lost. 

I spent this last weekend at the wedding of one of my best friends. I was Best Man, in fact. The weekend concluded my ninth wedding in a 12 month period. That time of life, I suppose.

Over the course of the weekend I couldn’t help but find myself thinking about the importance of communities. I thought about how these communities change over time and how one’s communities are colored by very distinct decisions they make in life. My friend is a surgeon and thus, many attendees of the wedding came from his med school or had a medical background. In contrast, the few of us from high school found ourselves talking about the same things we talked about as teenagers - indie rock bands and general shenanigans.

I was reminded of a pretty simple equation: the decisions that my friend Charles made to become a doctor and to go to med school, shaped the community he had. In turn, the communities he continues to choose to be a part of today influence the way he processes information and experiences.

Thinking back on my own life, the communities that I am a part of are a direct effect of these decisions (not an exhaustive list):

• the decision to go to Brown University
• the decision to play tennis throughout high school
• the decision to pursue a BA in Race and Ethnicity
• the decision to work at Google and Amazon
• the decision to leave NY and move to Los Angeles
• the decision to pursue Olympic Weightlifting competitively

I wrote this list out as a quick exercise. I find it helpful for a performance oriented workhorse like myself. While many of these decisions were made because of the achievements they promised, today I reflect on them with a focus on the communities they provided.

Thinking about the driving forces behind what makes strong communities is important because having strong communities is what makes me feel human. It’s what makes me feel explicitly connected to something that is larger than myself and thus, allows me to be more present. The farther away I feel I am from communities, the smaller my world becomes and the more I feel I need to be at the center of that very small world. The closer I am to my communities, the more space I have to be present. That is not an ‘achievement’. That is something different and it feels nourishing. 

• I started a new job. 
• I changed teams at that new company and have scope of responsibility increase dramatically.
• I met a nice beautiful lady. 
• That nice beautiful lady and I moved in to a new home together.
• I moved cross the country and left my beloved New York City for the canyons and sun of Los Angeles, California. 

Thinking about all of those events, I can say that while it wasn't too much, it was a lot of change to manage. What I experienced was that these changes disrupted my routines, put me outside of my comfort zone, and ultimately invoked me to ask whether existing routines and frameworks previously used to rule my life were obsolete. Where I once found solace in several habits and routines, I no longer found myself able to:

• meditate regularly first thing in the morning
• write frequently 
• create podcast episodes and audio stories with project partners
• schedule 'no email focus time' at work for the first two hours of the morning on the east coast and schedule meetings with west coast teammates in the afternoon
• rely on the same friends to round up for dinner on Friday evening
• use my subway commute in NYC to ease into the work day with music of my choice

I found myself on an airplane most weeks of the month than not, learning to work daily with a team on both coasts, and carving out space for two instead of one in my day.

Eventually I did make some very conscious decisions to ease the change like easing back on the blog and writing time in order to give myself more time to play and become part of a community in my new home, dedicate time to create new experiences with my girlfriend, and switch to receiving my news through podcasts in the morning instead of my phone so that I could reduce strain on my eyes knowing that the day would be long and include much more inflow than my previous job.

However, the change with the most impact has come from David R Hawkin's Letting Go: The Pathway of Surrender, which my friend recently gave to me. I am not even finished with the book and I feel compelled to document my notes so that I can further cement my takeaways in my memory (very bad rule writing notes on a book you haven't finished. Doing it anyway!) 

Dr. Hawkins' book is not too dissimilar from what I learned in Vipassana meditation retreats, so I found the approach to be very familiar and easy to access. The first third of Letting Go is an exposition on the art of letting go and how to relieve oneself from the strain of negativity. Very similar to inspirational t-shirts and Instagram posts with nice fonts fitting for a Sunday morning with pour over coffee. But more interesting is the work Hawkins spends on diving into very specific emotions. He takes 30 - 50 pages to thoroughly describe apathy, depression, grief, fear, desire, anger, pride, courage, acceptance, love, and peace. These emotions construct a spectrum of emotions or mental mechanisms. In other words, these emotions are how we choose to handle experiences through "suppression, expression, and escape."

Some choice passages that don't need explanation:

The reason to let go of selfishness is not because of guilt. Not because it's a 'sin.' Not because it's 'wrong.' All such motivations come from lower consciousness and self-judgment. Rather, the reason to let go of selfishness is simply because it is impractical. It doesn't work. It's too costly. It consumes too much energy. It delays the accomplishment of our goals and the realization of our wants. Because of its very nature, the small self is the creator of guilt and its self perpetuator; that is, out of guilt we strive to accomplish and achieve success. Then, when we achieve success, we feel guilty because we have it. There is no winning of the guilt game. The only solution is to give it up, to let it go.

The general progression of the levels of consciousness, as we go from the lowest to the highest, is to move from havingness to doingness to beingness. At the lower levels of consciousness, it is what we have that counts. It is what we have that we want. It is what we have that we value. It is what we have that gives us our self-image of worth and position in the world.

Actually, the way something comes into our life is because we have chosen it. It was the result of our intention, or we made a decision for it. It has come into our life in spite of desire. The desiring was actually the obstacle to its achievement or acquisition. This is because desire literally means, 'Id o not have.' In other words, if we say that we desire something, we are saying that it isn't ours. When we say that it isn't ours, we put a psychic distance between ourselves and what we want. This distance becomes the obstacle that consumes energy.

In looking at fears, then, it is well to remember that Carl Jung saw this reservoir of the forbidden inside the shadow as a part of the collective unconscious. The term collective unconscious means that everybody has these thoughts and fantasies. There is nothing unique about any of us when it comes to the way we symbolize our emotions. Everybody secretly harbors the fear that they are dumb, ugly, unlovable, and a failure.

Glamorization is living at a fantasy level...because there was no reality in it, the world is constantly selling us dishonest, catering to our desire for that romantic, glamorized aspect. it promises to make us more important than we really are. Glamour at that level of dishonesty is a fake.

If we constantly follow this procedure, we will come to the awareness that everyone in our life is acting as a mirror. They are really reflecting back to us what we have failed to acknowledge within ourselves. They are forcing us to look at what needs to be addressed. What aspect of our smaller self needs to be relinquished? This means that we have to constantly let go of our pride in order to undo anger, so that we can be grateful for the continual opportunities of growth with which we are presented in the course of everyday experience.

While Letting Go has not actually led to any tangible changes in my day (yet), spending time with this book has been enough for me to 'jump the hurdle' from 2015's shakeup and allow me to land well into 2016. Whatever that means.

I thought a lot about whether or not to post this. But 2015 was a year of change for me, and as I’ve said before, finding time to write about my experiences helps me bridge that gap to conclusion. Last year I started a new job. I moved across the country to Los Angeles. I moved in with a person that I love. And now that I’m on the other side of 2015, I can look back and see that I was slow on my feet for those last few months of the year. 

Change is hard. Looking at some of my biggest changes, I see two tools that help bring familiarity in periods of change. The first is patience (I’m the first to say that I don’t have enough of this). The second is putting in active effort. So I am posting this now as an effort to declare (mostly to myself) that I am actively working to make a new home. 

I am going to start with one new change right here. 

In 2016, I am going to start regularly posting my blog on social media, contrary to what I’ve been doing the previous five years. That sounds dumber that it is. In fact, it’s still pretty dumb, unimportant, irrelevant for 99.9999999% of the world. But the decision is symbolic for me. 

When I started this blog five years ago, my goal was to use writing and the blog as a way to continue my efforts to synthesize content and information instead of merely consuming it. I felt deluged by posts on Facebook and the millions of articles sent to me through email. And I wanted to continue deriving my own conclusions and opinions, similar to how a college student defends hypotheses in a course essay. 

I still plan on using this space in the same manner. But I’m going to be more public about it. 

But like many I have a list of reasons why I don’t think I should be writing publicly. I very much think writing (even blogging) is a creative endeavor. And anytime someone undergoes a creative endeavor what they are doing is undergoing risk. There are always reasons not to do something. Have you ever found yourself holding back on a project or getting cold feet about a decision? I do. There is power in simply naming those fears, putting them down on paper, exposing them so that they can be taken down. 

Elizabeth Gilbert’s Big Magic espouses a very similar practice. In Gilbert’s book she reads her own list of fears. The list is built of reasons why one might reject big magic and inspiration even when it chooses to present itself. I was inspired enough to create my own list. And now I am going to share my list of reasons why not to do something, even if that something is as simple as posting regularly on a blog. 

1. I’m afraid of what others will think of me and what I have to say.
2. I’m afraid of other people thinking I have no credibility. 
3. I’m afraid I don’t have enough credibility. 
4. I’m afraid I have no talent. Or better put, I’m afraid that the gap between my taste and my talent is too wide. I can recognize good work or good art. But that doesn’t mean I can create something equally good myself. 
5. I’m afraid I won’t be able to continue my day job and create or write on the side. 
6. I’m afraid of leaving the very safe confines of my day job. 
7. I’m afraid that I’ve neglected my blog for far too long that everything I put out will feel rusty and less than my best. 

Numbers 1 through 3 comprise probably 80% of the total weight of my fears. They will probably always be there. But this year, I will consciously act in the face of them. It will be a change for me. And change is hard.

But I’ve already thought about that.  

There's a strong quote in the interview that resonated with me: "Often times, the people that need meditation the most are the people who might also be most likely to quit because they like doing everything successfully." I am not shy to name my addiction to overachievement and this quote from Tara acknowledges the truth that meditation is not something to conquer, but instead a way of understanding how to categorize and employ a framework of living. 

I discovered four categories of insight from the interview:

(1) The Trance of Unworthiness:
When Tara first started getting involved in meditation (she actually lived in an ashram for ten years after college), she went through a lot of the same things I myself go through and the things I hear my friends go through in our present day Western culture which is the question: 'What else can I do to relieve myself of anxiety and stress?' The short answer? Relax more. Tara describes this relentless desire for self-improvement as the trance of unworthiness. And it comes from a mindset that lives in a world of scarcity and not one of abundance and self-love. 

(2) Balance
In my conversations with peers, another problem that is posed is this: What is the balance between acceptance and pushing the boundaries to increase progress? This refers to either self-progress and self-optimization in the personal life, or progress within a specific job function or company. I've thought long and hard about Steve Jobs' accomplishments and what he had to sacrifice to fulfill those, for example. Here, I enjoy Tara's pull from Carl Rogers: "It wasn't until I accepted myself just as I was that I was free to change." 

(3) What does successful meditation look like?
Okay, a bit of a paradoxical question, but my point is that for those of us who want to live a life not removed from civilization (i.e. I don't see myself moving to the mountains of Nepal anytime soon), what is the end goal? To this, I enjoyed Tara's point: The goal isn't to live life without any pleasures or desires (materialism, satisfactions, etc), but the goal is to be aware of when there is tight gripping and control of those objects, rather than the other way around. There is a difference between thinking of Buddhism and mindfulness as an ideal state of being without any desire, and thinking of Buddhism and mindfulness as a state of awareness of what those desires are. 

As an aside: I found some really great pointers in the interview geared towards giving a better way to meditate for the first time. Around the 1:30 mark. 

(4) Having tea with Mara
In Buddhist mythology, there is a popular story that describes the Buddha going out to have tea with Mara. In the Buddhist mythology of Buddha's awakening, one night Buddha sits under a bodhi tree (later known as the tree of awakening). Through the night, the god mara (Mara represents all the forces that create misery. Think jealousy, greed, desire, etc) attacked him. Instead of reacting with emotion, Buddha employed a practice of presence mind thinking so that every arrow, so to speak, was turned into a flower petal. Over the course of Buddha's life, Mara kept showing up. And the Buddha’s reaction to Mara was always to employ an attitude of calm and chill, despite more explosive cries from the guards and the caretakers who would sound the alarms with Mara's presence. In those moments, Buddha would go up to Mara and say, “Hi Mara. Good to see you. Why don’t we go have some tea?"

Okay, so...my two takeaways from the story: 1) Awareness: Buddha sees what is happening in this moment. He has a capacity to acknowledge what is here. Instead of fighting what is here in the moment, there’s an ability to create space for it and find a way to live with it. It’s a way of being with ourselves that is intimate and full, not part in part. 

Both of these together are radical acceptance. And with this, when we respond to the world, we get to respond to the world with our full selves and with our full potential. We aren’t in a reactive mode. 

“Between stimulus and response, there is space. And in that space is your power and freedom.” - Viktor Frankl

(5) Dealing with FOMO (fear of missing out)
I will keep this one short. There's a way to feel fear without being driven by it. There's a way to say that you're going to take a step back and take a sabbatical. This is the exact kind of relationship we can have with FOMO if we want to feel more liberated.

"The hero and the coward feel the same t hing. It's what the hero does that makes him different." - Mike Tyson

Tara ends the interview: "Ask yourself: What am I unwilling to feel?" To become fearless, you first have to feel the fear.

I hope this list will grow over time. To that end, if you are a close friend or family member of mine reading this, please continue to share with me, and I will do the same. The list below, of course, is a reflection of your presence in my life. Thank you.

Another disclaimer before I start: I have never been afraid or shy of platitudes. 

1) "Work hard, be kind, and good things will happen to you."
This was stolen from Conan O'Brien's speech on his last episode of The Tonight Show. In moments of overwhelm and when I feel like I can rationalize myself onto either side of a decision, I revert to Conan’s simplification of…everything. At the end of the day, if you can work hard and be kind, good things will happen to you. 
Thank you Amanda, for bringing me to Team Conan at an early age. I think I was 12 when I first saw Triumph The Insult Comic Dog. My conscience has never been innocent since. 

2) "The really important kind of freedom involves attention and awareness and discipline, and being able truly to care about other people and to sacrifice for them over and over in myriad petty, unsexy ways every day. That is real freedom." 
I appreciate the entirety of David Foster Wallace’s This Is Water speech and I return to it periodically to remind myself that the hardest moments to maintain a sense of selflessness are in the mundane - the trips to the grocery store, the boarding of an airplane, driving in traffic. 

3) Make decisions.

4) Before making a major life decision, ask myself this: What would I do if I wasn’t afraid?
It is incredible how much clearer this can make decisions. 
Thank you Emily S., for being my big sister. 

5) Learn how to say yes. Then learn how to say no. 
A lot of my time in college and my first couple of years after college were spent saying yes. It’s a fairly easy thing to do in a place like New York City, where there are no shortages of events, activities, and people. But saying no is simply another way to reserve your energy for saying yes to the things that matter most. 
Thanks Dan, for showing me the power of essentialism. But I’m still waiting for my ficus tree. 

6) Never let the amount of time it takes to accomplish something stop you from doing it. That time will pass anyway.

7) Complain less.

8) You can remove a lot of anxieties by distilling your to-do list to the one true thing that needs to be accomplished on any given day.

9) Confidence is being able to say I don’t know, but I can try to find out. 

10) Friendship is like anything else in life. The more effort you put in, the more you get out. 
Thank you Dan, for letting me make a video on your birthday that makes fun of every habitual Dan-ism. And thank you Phil, Tony, and John for making that video with me.

11) Read more.
There are so many good books and each one of them has unique ideas and worlds. In this weird way, books are the most affordable ways to have experiences.
Thank you Michael R. for teaching me how to read critically. 

12) Find your own metrics of success.

13) Find a way to have an impact on the inequities our systems have set up. 
I used to think that tackling systemic inequities and inequalities were the kinds of problems that took centuries of years and masses of people to re-correct. But adopting that kind of thinking sometimes overlooks the many ways to make smaller contributions, like volunteering a weekend, becoming a mentor, donating wisely, or becoming fully informed on an issue.
Thank you Amit and Anish, for engaging with me every week on these challenges.

14) Some of the best advice that’s ever been given to me came from people who were really good at listening, not necessarily at speaking. 
Also not a bad way to think about business relationships and identifying areas of collaboration across multiple stakeholders. Not being able to listen well means not being able to identify and name the situation. 
Thank you Erika, John C., Matt, John T., Frank, and Yu-Im for showing me what this means in our work. 

15) Take calculated risks. 
Sometimes the riskiest choice is the one that seems the most safe. When I left Google, I remember asking myself, “If I can't make jumps in my career now, then how else was I going to teach myself the excitement and joy of new adventures?" What seemed to be riskier was depriving myself of experiences because of fearful decision making, especially this early in the game. 
Thank you Todd for the healthy hunger. And thanks, Jon A. for leading by example.

16) Try not to take yourself too seriously.
Thanks Charles, for not being ashamed of having the goofiest laugh on record, from the age of 12 when we first met until now. 

17) As much as possible, try to employ a mind of realistic optimism. 
Recently I was at a show - The Together At Last Tour with Pete Holmes and Rob Bell. Early in the first act, Rob Bell described three different frames of mindset. The first was naive optimism, the mind that sees the world glass half-full while turning a blind eye to the many challenges of the world. The second mindset was one of defeated pessimism, the mind that allows cynicism to override action. The third mindset expressed a hybrid of the two - realistic optimism, the mind that acknowledges all of the bad, but chooses to stay hopeful. The example given in the show was a meeting between Desmond Tutu (who has witnessed apartheid at its worst) and the Dalai Lama (an exile of his own homeland) where upon seeing each other for the first time in years, they hugged and laughed for entire minutes at a time. Rob Bell finished this story outlining how both of these figures have seen more of the bad than we might ever, but they still choose to live with realistic optimism. 

18) Focus on doing one thing at a time. Less multitasking.
Even with the small things. Brushing your teeth. Washing the dishes. Waiting in the elevator.
Thank you Tomas, for bringing a practice of daily meditation into my life. 

19) Say I love you to friends and family more.

20) Commitment is continually willing to try harder.
Thanks B.

21) F = F
Fat = flavor. Perhaps the biggest bang for your buck cooking tip. 
Thanks Julian for bringing me into the kitchen.

22) Don’t look at a phone or desktop for the first hour of the day.

23) A lot of success is keeping calm and coming up with a plan.
Try not immediately reacting to the disaster, and see what fixes itself organically. Because disasters always happen. Additionally, the really good people are able to define next steps instead of wallowing in the resistance. 

24) Savor the Beginner’s Mindset and the road to learning new things.
The other way to read this is to emphasize the process, not the product. The happiness of pursuit, not the pursuit of happiness. 
Thank you Mom, for putting me in more extracurricular activities than necessary while growing up, for showing me how to teach myself, and for showing me how to pick my strengths and weaknesses. But for the record, I still think I could have made it to the NBA. 

25) Spend some time strengthening weaknesses. They don’t have to be as well developed as your strengths, but don’t make them liabilities. 
Growing up I loved playing point guard and using my quickness to drive into the lane for quick lay-ups. But I was only able to do this with my right hand, which effectively cut off half the space on the floor for me to work with. I never got as good at shooting lay-ups with my left hand, but I eventually built up my left-hand weakness so that it didn’t give defenders an easy way to shut me down.
Thank you Dad for the shooting drills in the driveway and the hallway.

26) The days are long, but the decades are short.
Stolen from Sam Altman, my inspiration for this post. Each night, if possible, take a couple minutes to think about all the great things that happened that day. 

1) Resume Virtues vs Eulogy Virtues
As Brooks defines them, "resume virtues are the skills you bring to the marketplace. Eulogy virtues are the ones that are talked about at your funeral - whether you were kind, brave, honest, or faithful."

2) The Gap Between the Actual Self and the Desired Self
"But if you live for external achievement, years pass and the deepest parts of you go unexplored and unstructured. You lack a moral vocabulary. It is easy to slip into a self-satisfied moral mediocrity. You grade yourself on a forgiving curve. You figure as long as you are not obviously hurting anybody and people seem to like you, you must be O.K. But you live with an unconscious boredom, separated from the deepest meaning of life and the highest moral joys. Gradually, a humiliating gap opens between your actual self and your desired self, between you and those incandescent souls you sometimes meet."

As far as I can tell, this gap has always existed for the overwhelming majority of the population. The desire and strive to close that gap is more indicative of a rich depth of character than actually having that gap closed. I believe Brooks gets to this when he discusses the philosophy of stumbling in his conclusion. 

3) The Philosophy of Stumbling
"The stumbler doesn’t build her life by being better than others, but by being better than she used to be. Unexpectedly, there are transcendent moments of deep tranquillity. For most of their lives their inner and outer ambitions are strong and in balance. But eventually, at moments of rare joy, career ambitions pause, the ego rests, the stumbler looks out at a picnic or dinner or a valley and is overwhelmed by a feeling of limitless gratitude, and an acceptance of the fact that life has treated her much better than she deserves."

This is easier said than done, especially in a place like New York City (or San Francisco, or Los Angeles, or Chicago, or Boston, or any other bustling metropolitan area bursting with professional ambition). But at the core of the Philosophy of Stumbling, what I enjoy most is the re-definition of ‘better’ as something that is derived from a carefully constructed set of individual values. Socially deconstructed and from within.

Random Sidenote: once a month seems like a considerably high frequency to be running into people radiating ‘inner light’, but major kudos to whatever you're doing with your daily commute, Mr. Brooks.

Thanks for sending along, Anand. 

Perhaps the five most dangerous words anyone has ever said upon observing a piece of work being done. 

Well, six months ago, my friends Samir, Anand and myself said these exact words. At the time, we were listening to podcasts. Plenty of them. So we spent the resulting half-year learning how to record audio, how to edit audio, and most importantly, how to speak in a clear manner and with enough personality to sustain a listener over 45 minutes of thought provoking dialogue. 

Now, I'm excited to present the first episode of Boombox The Podcast. 

Boombox is about longform discussion in a shortform world. Mostly, Samir, Anand and I felt like all too often we'd be swiping through our news feeds. An article would go viral, we'd see the flippant commentary, and then we'd think to our respective selves, "Hmm. I wish I could have a longer conversation about that."

We also felt like there was this consensus about Millenials. And the consensus held that Millenials valued shortform informational transactions - tweets, six-second Vine videos, and three sentence customer reviews. But there's a large percentage of the Millenial demo who still value longform conversation, Socratic methods of dialogue, and even debate. 

Boombox is our attempt to bring that conversation to an audience willing to listen. I hope you'll be one of those people. Each week we'll pick one news trend and examine it through all angles. In the past few weeks as we've developed 'rehearsal episodes', we've looked at tweets immediately following Transparent's Golden Globes acceptance speeches. We listened to other podcasts reporting on gentrification, and we even asked strangers what they think about modern love and the quickest way to fall in love, when Mandy Len Catron's NYTimes piece went viral. 

And if you think the Boombox namesake is in homage to arguably most famous and greatest modern movie romance, you're entirely correct. Maybe we'll explain that homage in an episode one day. Only one way to find out...

A friend of mine recently read that initial blog post and in response to the questions brought up by Being Mortal, she shared with me her daily mantra: 

I am of the nature to grow old. There is no way to escape growing old.
I am of the nature to get sick. Every body experiences illness.
I am of the nature to die. Every living being experiences death
All that is dear to me and everyone I love are of the nature to change and I will one day be separated from them.
My actions are my only true belongings.
Every action unavoidably begets many reactions. My actions are the ground upon which I stand.

Thanks, Anna. 

For these reasons, I found myself cautiously optimistic about spending over a week in the country (meanwhile, my parents found it to be a slightly boneheaded idea and certainly unsafe, though the phone call to my parents didn’t seem out of the ordinary from any other idea I normally would bring to the table). 

The truth is, Medellin was just named the world’s most innovate city by WSJ and Citi, beating out New York City and Tel Aviv in 2013. If you know me, then you know that there’s nothing I love more than  turnaround underdog stories (Jeremy Lin, Rudy, and Tony Robbins, to name a few). So I sent a few calls out to some friends and organized a trip to Bogota and Medellin. 

Here’s the short version: I truly believe Colombia has everything. Outdoor hikes with scenic views and discotheques with dance floors running until 5 am. Hip speakeasy rooftop bars (I could have been back home in Brooklyn) and hole-in-the-wall bars with $1 local beers. There’s certainly no lack of culture or history either. Really, no place in the world isn’t without a story but Colombia’s is doubly interesting.

In Medellin, we found ourselves in Comuna 13, a neighborhood once riddled with violence as territory disputes between the paramilitary and counter paramilitary groups ensued throughout 2001 and 2002. To minimize deaths of children and women, curfews were implemented at 5 pm each day. Walking through the neighborhood today you’d never know, but the visit for me represented so much of Colombia’s story the past twenty years. Andres, a 22 year old local, shared with us his story, as we walked around the neighborhood. During the occupation he was 9 years old and now he works for the city. As he was telling us this story I could sense his eagerness, as if my friend and I along with any other tourist resembled shiny new visitors in a home. The pride and joy of being able to show someone a piece of your work, I imagine, has to be one of the most universal sentiments. 

We spent another day visiting the parque biblioteca, otherwise known as a library designed to bring books and computers to the Santo Domingo neighborhood. A woman working at one of the exhibits told us the controversy over having the library built. When plans first went up, neighborhoods debated, with some arguing that civic engagement related projects like libraries and public art were less essential than other needs like hospitals and the complete excavation of bomb and assassination sites. In the end, the consensus landed on building spaces for civic engagement. Why? Because creating hope means remembering spaces that were once dangerous, not erasing them with new varnish and window dressing. In the particular example below, Colombian sculpture artist Fernando Botero and the city erected an identical sculpture of a bird next to a the previous 'parent' sculpture that had exploded into pieces after a public bombing. 

I think this mentality accomplishes two things for Colombia. It commits to memory the lowest places the country has been. But more importantly, it shows to both locals and foreigners how hard the country has worked to become what it is today.

---

We found an exhibit in the library labeled “Cual es tu patrimonio?” which translates to “What is your heritage?” Our host invited us to make drawings of Brooklyn and the New York City skyline so that we could show our own heritages. When we finished drawing, we pinned them up on the wall next to the many other cut-outs of construction paper. On them were the names of cities from around the country: Medellin, Bogota, Cali, Barranquilla. And it didn’t seem like for a second, anyone had forgotten where they had come from. 

Proven by the hilarious Uber for X poem that's been breezing across news feeds, there's a large number of tech based startups promising a marketplace that matches people willing to pay for convenience with people seeking flexible work. In the world of Uber that means pairing people willing to pay for drivers with people willing to drive. With dressing, this sounds like something called the sharing economy. 

Without dressing, this sounds more like wealth inequality. 

How is this wealth inequality exploited? Three main ways, if I'm reading the takeaways in the latest coverage from Quartz and The Dish.

1) The market needs to be big enough to scale.
Here are some great examples: food, laundry, taxi rides. According to Quartz: "Without that, it's just a concierge service for the rich rather than a disruptive paradigm shift, as a venture capitalist might say.

2) The labor class needs to be willing to work at low wages.
Also from Quartz: "There needs to be a large enough labor class willing to work at wages that customers consider affordable and that the middlemen consider worthwhile for their profit margins."

Which of course begs the questions, what are Uber's margins, what are their main costs, and what share of profits do they take from drivers? 

3) The company responsible for the marketplace needs to contract laborers to forego a percentage of profits and cover a percentage of costs.
As reported by The Dish, Uber takes 20% of all profits from each drive and car maintenance, gas, and insurance costs are covered by the driver. So the answer to the aforementioned begged question: very high. Uber's margins are very high. 

I liked Leo Mirani's summary best:

There is no denying the seductive nature of convenience—or the cold logic of businesses that create new jobs, whatever quality they may be. But the notion that brilliant young programmers are forging a newfangled “instant gratification” economy is a falsehood. Instead, it is a rerun of the oldest sort of business: middlemen insinuating themselves between buyers and sellers. All that modern technology has done is make it easier, through omnipresent smartphones, to amass a fleet of increasingly desperate jobseekers eager to take whatever work they can get.

The two speeches are Robert F Kennedy's announcement of MLK's assassination and a mere 63 days later, Ted Kennedy's eulogy for RFK following his assassination. 

I will keep this short because the beauty really is in the words themselves, with little need for commentary. 

We can do well in this country. We will have difficult times. We've had difficult times in the past. And we will-we will have difficult times in the future. It is not the end of violence; it is not the end of lawlessness; and it's not the end of disorder.

But the vast majority of white people and the vast majority of black people in this country want to live together, want to improve the quality of our life, and want justice for all human beings that abide in our land.

Thanks Dan, for the timely reminder of these words.

As an industry known for it's white frat boy and white geek boy communities, Silicon Valley is severely lacking in diversity both with regards to female leaders and leaders of color. And this is why Tristan Walker's story is novel. As an African American post-graduate, Walker first worked on Wall Street, then as an intern at Twitter, then as Foursquare's first bizdev leader, and finally as entrepreneur-in-residence at Andreessen Horowitz. Today he runs his start-up Walker & Co., which is focused on providing personal care products for people of color.

(I won’t lie about how my biased excitement for Tristan Walker's feature in Fast Company is based on the fact that the man was schooled through New York City's Sponsors for Educational Opportunity (SEO), a program that works to place students of color with colleges and job opportunities for upward mobility. For context, I've been working with SEO as a mentor for two years and have been following their work for four.)

When topics of race filter through my feeds, conversations tend to focus on how the dynamics of race are embedded in government systemic structures that then bleed into the day-to-day (Hello, Ferguson). But this also holds for the corporate structures set up in the largest tech companies.

From Fast Company:

It is racist, for example, to approach a recruiting firm with the mandate to fill an engineering position only with someone from one particular Ivy League school, where blacks comprise a single-digit percentage of the student population. it is racist to rely on employee referrals for hires, when the typical social network of a white American is 1% black.

In the entrepreneur courses I've taken and the millions of articles bouncing around Twitter, I always see an emphasis placed on consumer research (also known as bottom-up research). When I look at Walker's mission, I'm surprised how something like Walker & Co.'s mission hasn't been tackled yet. Of course, this is the point of Fast Company's feature but it's still worth emphasizing.

Silicon Valley wants its founders to shoot for the biggest customer base possible, but in so doing they risk missing a chance to back companies that might very profitable rule a strong minority niche. Late last year, Nielsen published a report on the spending habits and media consumption of African-Americans, urging corporations to 'think and behave differently toward valuing African-Americans and their economic impact.' The report indicated that black consumers, whose buying power is estimated at $1 trillion, spend nine times as much on products in the 'ethnic hair and beauty aids' category than other groups. In other words, it's a lucrative market that deserves much more than copper-tone boxes on a shelf.

I don't often put my Bachelor's Degree in Race and Ethnicity lens on in application to business related issues (but clearly I should). And I suspect this is the conversation that people like Tristan Walker (and David Drummond, and Tyler Scriven, and Erin Teague, and even Ben Horowitz) are asking us to have more and more often. 

For an industry that thrives on disrupting the mainstream, it might be worth asking whose mainstream is the focus of disruption.

The gist of 1,000 True Fans can be stated simply:

A creator, such as an artist, musician, photographer, craftsperson, performer, animator, designer, videomaker, or author – in other words, anyone producing works of art – needs to acquire only 1,000 True Fans to make a living.

A True Fan is defined as someone who will purchase anything and everything you produce. They will drive 200 miles to see you sing. They will buy the super deluxe re-issued hi-res box set of your stuff even though they have the low-res version. They have a Google Alert set for your name. They bookmark the eBay page where your out-of-print editions show up. They come to your openings. They have you sign their copies. They buy the t-shirt, and the mug, and the hat. They can’t wait till you issue your next work. They are true fans.

In a word where finding an audience and publishing really is as simple as a tweet, a Tumblr post, or a Squarespace website turned into an ecommerce business, the possibility of having a long tail of "lesser fans" is real. The challenge then is to make those lesser fans True Fans. And people and companies do that by personally connecting, again through various channels of social media or dark social. 

One final a-ha from Kelly's idea that I find important:

But the point of this strategy is to say that you don’t need a hit to survive.  You don’t need to aim for the short head of best-sellerdom to escape the long tail. There is a place in the middle, that is not very far away from the tail, where you can at least make a living. That mid-way haven is called 1,000 True Fans. It is an alternate destination for an artist to aim for.

Young artists starting out in this digitally mediated world have another path other than stardom, a path made possible by the very technology that creates the long tail. Instead of trying to reach the narrow and unlikely peaks of platinum hits, bestseller blockbusters, and celebrity status, they can aim for direct connection with 1,000 True Fans. It’s a much saner destination to hope for. You make a living instead of a fortune. You are surrounded not by fad and fashionable infatuation, but by True Fans. And you are much more likely to actually arrive there.

"That's wrong and irresponsible". Atul Gawande didn't say that to me directly, but based on his newest book, I feel like that is what he would say to me in a one on one conversation. Growing old and becoming mortal is perhaps one of the most important elements of life we have yet to understand fully, and Atul Gawande makes that point through a mix of factual evidence and anecdotes in his latest book Being Mortal. 

Below is a list of things that I learned from Being Mortal that I did not know beforehand:

1) The Hill-Burton Act of 1946, which provided federal grants and loans for hospital construction, is both the most high impact and the most overlooked piece of healthcare legislation to pass through Congress. This act is responsible for financing over nine thousand new medical facilities, in turn creating the the new field of medicine and the modern hospital today. 

2) Only in the 1980s did assisted living facilities come into fruition when Keren Brown Wilson attempted to build an alternative to nursing homes so that "she could create a place where people could live with freedom and autonomy no matter how physically limited they became." Just because you are old and frail, doesn't mean you have to submit to life in an asylum, which is how some perceive nursing homes to be, with their rigorous routines and rules. 

3) Health professionals have agreed upon a formal classification system for a set of capabilities that collectively define whether a person is fully functioning. These attributes are called the "Activities of Daily Living" and they are:

• using the toilet
• eating
• dressing
• bathing
• grooming
• getting out of bed
• getting out of a chair
• walking

Inability to perform any of these eight activities deems a person incapable of basic physical independence and in need of a nursing home or some kind of assisted help. 

4) "As medical progress has extended our lives, the result has been what's called the 'rectangularization' of survival. Throughout most of human history, a society's population formed a sort of pyramid: young children represented the largest portion - the base - and each successively older cohort represented a smaller and smaller group. In 1950, children under the age of five were 11 percent of the US population, adults aged forty-five to forty-nine were 6 percent, and those over eighty were 1 percent. Today, we have as many fifty-year-olds as five-year-olds. In thirty years, there will be as many people over eighty as there are under five. 

5) The definition of "socioemotional selectivity theory": "how we seek to spend our time may depend on how much time we perceive ourselves to have. When you are young and healthy, you believe you will live forever. You do not worry about losing any of your capabilities. People tell you "the world is your oyster," "the sky is the limit," and so on. And you are willing to delay gratification - to invest years, for example, in gaining skills and resources for a brighter future. You seek to plug into bigger streams of knowledge and information. You widen your networks of friends and connections, instead of hanging out with your mother. When horizons are measured in decades, which might as well be infinity to human beings, you most desire all that stuff at the top of Maslow's pyramid - achievement, creativity, and other attributes of 'self-actualization.' But as your horizons contract - when you see the future ahead of you as finite and uncertain - your focus shifts to the here and now, to everyday pleasures and the people closest to you."

6) There is irony (and also poetic flair) in this conversation: The field of medicine focuses primarily on the science of preserving life, but rarely do we speak about the art of being mortal. Gawande's book was the first time I'd ever looked at that art seriously. 

These words come from Bough Bonin, Global Head of Media for Mondelez, the company responsible for Oreos, Chips Ahoy, Honey Maid, Ritz, and undoubtedly the best of them all, Nutter Butter. In the digital marketing world, Mondelez has been on a tear the past couple of years, evidenced by both the year-end round of advertising awards that are shipping off to Bonin's team and the ample coverage of Oreo's Dunk in the Dark tweet during last year's Super Bowl blackout. 

In the latest Fast Company feature, Bonin riffs on the current state of digital, of which there are several industry wide problems (audience fragmentation, multi-screen attribution, to name a few). Bonin presents his take on one of these problems - programmatic - and while programmatic is not a new conversation, what's refreshing about Bonin's take is that he's started to anticipate problems that seem to be two or three steps down the line from where the industry is now.

By and large, the industry conversation on programmatic is focused on real-time buying. Marketers are looking to understand different inventory pools across networks and exchanges, by video and display formats. Programmatic, based on the current conversation, is entirely synonymous with the buying process of advertising. The advent of real time content creation is likely one or two years down into the future. The Fast Company feature continues:

'Imagine if at that moment we had been able to programmatically change every piece of media that we were buying to turn on the Oreo ad,' [Bonin] explains, using a recent buzzword - programmatic - to describe the trend of automated real-time ad buying.

...'People look at programmatic as cost savings right now. It's way more strategic. Imagine a marketer who can create video in real time and buy ad space in real time. It was at that moment we realized that there was a bigger game that we weren't prepared to play.'

My guess is that as programmatic video buying grows into the mainstream, programmatic content development will become more of a focus. Looking at today's eMarketer projections we expect only 40% of digital video ads to be purchased programmatically compared to 75% of display ads. 

The closest analog I've seen to real time content development recently is Honey Maid's This is Wholesome campaign. After receiving a number of criticisms for including a gay family in it's commercial, Honey Made responded quickly by developing another commercial responding to haters with love. The result was a real time reaction that involved the rapid deployment of a creative team to develop the idea and the flexibility of distribution channels to provide the message to the right audience.

And all of this matters perhaps because content itself is becoming shorter and more snackable (And believe me, when 8 second Vine videos are getting the same reach as a highly rated TV network show then you know content is becoming shorter and condensed). As that content becomes shorter, we should expect the demand for producing content quicker to grow and the real time buying and real time content development conversations to advance in parallel.

1. Business organizations love frameworks. They help scale ideas. 
2. Business frameworks don't always work. Most of the time, actually, they don't.

The paradox of frameworks is that solutions require structure in order to move from one mind to another, but so many growth challenges (both in business and a career) are unique enough such that no one framework can be plugged in. Instead, solutions are customized to the problem, which is to say that there is no directly applicable framework. 

Part of this paradox is quickly summed up in Peter Thiel's book Zero to One: Notes on Startups, or How to Build the Future:

Every moment in business happens only once. The next Bill Gates will not build an operating system. The next Larry Page or Sergey Brin won't make a search engine...If you are copying these guys, you aren't learning from them. 

Of course, it's easier to copy a model than to make something new. Doing what we already know how to do takes the world from 1 to n, adding more of something familiar. But every time we create something new, we go from 0 to 1. The act of creation is singular, as is the moment of creation, and the result is something fresh and strange. 

I look at the many pieces of career advice I've received from parents, friends, and older colleagues. I also look at success stories across my organization at work. The consistent thread has always been "Hey, here's what I did when I faced that scenario," or "Hey, last time we broke through a large deal, this is how we did it." And this is because frameworks help tell the story of what going from 0 to 1 looked like. Frameworks are attractive because they help bring clarity and understanding. 

After reeling off of the success from Toy Story, Pixar's first movie, president Ed Catmull found himself asking how that movie became a success and how much of that success was his doing. 

He walks through his answer in an episode of Tim Ferriss' podcast:

What we did together is not something I can separate myself from. This is true of most enterprises. The desire to separate oneself is like asking for a clean answer to a question when there is no clean answer. And it is true with most of the things in our lives whether its business or personal is that the inner connection between them and how they're all mixed up together is inherently messy, confusing, and there aren't clear boundaries. And the desire for complete clarity actually leads one away from addressing the mess that's in the middle.

In another episode of Tim Ferriss' podcast, Kevin Kelly, co-founder of Wired magazine and a million other things, brings the same argument for novelty to his definitions of professional success. 

The great temptation that people have is that they want to be someone else which is to say that they want to be in someone else's movie. They want to be the best rockstar. And there are so many of those already that you can only wind up imitating somebody in that slot. And I think to me success is making your own slot. You have a new slot that didn't exist before. That's what I chalk up as success - is making a new slot.

My slot would be Kevin Kelly. That's the whole point. The slot isn't going to be a career or an imitation of someone. That is success. You didn't imitate anybody. If you become an adjective that's a good sign. So I think success is making your own path. If they're calling you a successful entrepreneur, then to me that's not the best kind of success.

In other words, frameworks can be helpful for making sense of how an idea solved a problem. Role models can be helpful for showing how a person navigated the tendrils of a career. But to create something new or to solve something new or to be something new means that only a fraction of that framework is going to be helpful.

So, then, why do we use frameworks and why do I see so many of them?

Here's another popular quote from John Maynard Keynes: "It's better to be roughly correct than precisely wrong." 

Frameworks help make the incremental next step easier. We use frameworks because looking for precisely correct means we never get from 0 to .00001 (this is because precisely correct doesn't exist). Not using frameworks means staying at zero. And that's the absolute worst.

I had entirely forgotten this quote (and the equally amazing film from which it comes from) until I came upon the reference in my reading of Brene Brown's Daring Greatly: How the Courage to Be Vulnerable Transforms the Way We Live, Love, Parent, and Lead. At least amongst my social circle (read: Millenials), Vulnerability is a hot new topic. I see a trove of articles thrown my way every day on how to be vulnerable, the importance of opening yourself up to the world, etc. And while these readings make sense to me, the talk always seems easier than the walk. There are a few great vignettes in Brown's book that allude to the "vulnerability hangover" - you know, that moment after you've opened yourself up and realize your mouth is a fire hose of overshare. 

So, naturally, I was excited to pick up Brown's book, which walks through what it means to be vulnerable and how to do it in a healthy, meaningful manner with the science of a psychologist's lens and without the suffering embarrassment of a vulnerability hangover.

Increase in "vulnerable" searches from 2009 - present:

Two points on vulnerability stood out to me: 

1) Use your uncool pool. 

Finding people you can be uncool around, to build on Lester's wisdom, is about finding the people closest to you and using their holistic perspective of who you are to help you reason through decisions. There is no firehose and there is no overshare if you're speaking to those closest to you, just honest dialogue. 

Brown identifies these people as the following:

"To be on that list, you have to love me for my strengths and struggles. You have to know that I'm trying to be Wholehearted, but I still cuss too much, flip people off under the steering wheel, and have both Lawrence Welk and Metallica on my iPod. You have to know and respect that I"m totally uncool."

Brown calls these friends "stretch-mark friends" because her "connection to these people has been stretched and pulled so much that it's become part of who we are, a second skin." I'm going to call these friends my "uncool friends" because I like the idea of having a group of people in my life where I can be uncool, un-scrutinized, myself. The irony in relying on this network of friends is that having a group of "uncool friends" means that at one point you've opened yourself up to them. On some level, whether by design or accident, these people have seen you stumble, they've seen you rise, and they've seen you everywhere in between. 

Brown goes so far as to write the names of these people on a piece of paper that she keeps in her wallet. I didn't do that, but I did write names of my uncool friends in the margins of the book. 

The utility of the uncool friends, according to Brown, is that they provide a trustworthy second or third opinion when trying to find balance:

"When we stop caring about what people think, we lose our capacity for connection. When we become defined by what people think, we lose our willingness to be vulnerable. if we dismiss all the criticism, we lose out on important feedback, but if we subject ourselves to the hatefulness, our spirits get crushed. It's a tightrope, shame resilience is the balance bar, and the safety net below is the one or two people in our lives who can help us reality-check the criticism and cynicism."

When I think about moments in my life when I've been vulnerable (oh, boy), I can remember the moments before, during, and after the vulnerability. I analyze them internally. And eventually, I walk that analysis through with my uncool friends. In that sharing one of two things will happen: over the course of the conversation I'll come to articulate something I could not have before, or my uncool friends will tell me I'm overanalyzing and the moment needs to pass. Both scenarios provide balance, help me understand why a vulnerable moment was worth my time. But the point is that I wouldn't have been able to go through that process without my uncool friends. 

2) Perfectionism is not self-improvement. 

Brown writes: 

"Perfectionism is, at its core, about trying to earn approval. Most perfectionists grew up being praised for achievement and performance (grades, manners, rule following, people pleasing, appearance, sports). Somewhere along the way, they adopted this dangerous and debilitating belief system: 'I am what I accomplish and how well I accomplish it. Please. Perform. Perfect." Healthy striving is self-focused: How can I improve? Perfectionism is other-focused: What will they think? Perfectionism is a hustle."

Looking at perfectionism with this definition is paralyzing, which is the point that Brown is trying to make, along with the notion that perfectionism is also an addiction. According to Brown, perfectionism lays opposite from worthiness. Perfectionism is cousin to a world of scarcity, where we can easily identify ourselves as not being smart/good/successful/fatherly/friendly enough. Perfectionism, as I read it, doesn't leave room in all its stifling wonder for vulnerability. 

When I think about the greatest inventors and creative minds that I admire today, I recognize the emphasis they place on feedback. To go through that feedback process correctly means opening oneself up for criticism. That criticism brings the creator closer to perfection, closer to a better piece of work, though the creator knows there is no perfection. There is a difference between perfectionism and excellence. Aim for the latter.   

--

Brene Brown also has her own TED talk, if you'd rather take a quick dip into the daring greatly world, instead of a deep dive into the book. 

The project: Google Reach, a skills-based volunteer project designed to bring together employees from different parts of the company. These teams of four or six partner with an organization in a developing country to lend a consultative service, understand the operations of the organization, the value brought to the table, and opportunities to go from point A to point B.

My team consisted of a software engineer from Poland, a marketeer from our Google.Org team, a manager from our data server operations group, and myself. All four of us had elected to engage in a social entrepreneurship project, which paired us up with Grameen Bank and the Negros Women for Tomorrow Foundation (NWTF), a microfinance institution located in Bacolod City in the island of Negros, Philippines. For a month prior to our touch down on the ground, the four of us met with our partners to scope the project, define deliverables and carve out roles and responsibilities.

To (impossibly) summarize our deliverable, we focused on a geospatial analysis leveraging Google Maps Engine so that NWTF could better understand the financial health of households in a given region. In doing so, we also developed a database much more maneuverable than the paper records currently held on file. This database is now in the hands of the research and development team at NWTF.

To put this visually, we went from this:

to this:

The team honed in on one neighborhood to develop a proof of concept, going out with loan officers into the field and simulating data collection. Before our departure, steps were put in place to implement and scale.

Great? Great. Now, what did I learn?

Every experience with a large chunk of time spent outside of your home will net you personal growth, and I’ve had a few three month and six month long experiences spent in developing countries that can attest to that. But I haven’t yet had that experience as a working adult with some (albeit only a few notches) career knowledge under my belt, which is why I feel the need to specifically call out a couple of takeaways that have contributed to my professional growth. 

1) Understanding the value of your skillset by taking it outside your normal day function

Working in a different country, working with a different team, and working with different partners, I was able to see my professional skills in action in a different context than my day-to-day back in New York City.

Flexing my strongest muscles is something I often do in my day job. But because we mostly function in our organizational silos, it can be difficult to understand what our true strengths are until you see yourself in a very diverse pool of talent. Working in a sales group focused on both advertising platforms and larger sponsorship programs means much of my day involves managing partners, finding opportunities for joint collaboration across companies, and communicating effectively.

Personally, I didn’t think too much about using this skillset when I started scoping our project with NWTF and Grameen Bank. Perhaps it was because whenever one signs up for a volunteer or 20% program, you tend to focus on the details of the project and your own professional limitations. I, for example, knew early on that I was going to be as useful as a doorknob when NWTF asked us to help integrate a Google Maps API into some of their existing databases. I would soon later find out, there were members of our team who could speak to this intelligently.

Taking my real strengths – communication and partner management – and seeing them provide valuable in a different context helped me discover this: that I truly enjoy using those skills. 

For career development, this is key. In college, I remember plenty of talk about transferrable skills. Why? Because it was mostly assumed that the bulk of us were too young and immature to know what we liked doing, what lit us on fire, what we found passionate. So in the meantime, best to round yourself out and make yourself marketable. There wasn’t as much talk around skills one liked using, probably because we were all young, starry eyed, and with zero work experience to baseline the likability of given work (this isn't to be confused with conversations around working in industries or fields that one felt passionate about, regardless of which skillsets are in use; there are plenty of those discussions in the pre-graduation pep talk).

What’s better than having transferrable skills? Possessing transferrable skills that you enjoy using. There’s an element of self-awareness here that is also appealing and I'm still gelling on that.

 2) Understanding the mission statement as another way to look at the big picture value 

My second professional takeaway hinges on how moved I felt by how seriously NWTF took to their mission statement. I go back and forth with mission statements, often because I feel that they can be used more for PR or shareholder purposes.

NWTF takes their mission statement seriously: to provide sustainable, financial, and client-responsive developmental services to the poor. Around 60% of their portfolio is living under the poverty line, compared to 30-40% for the ~100 other MFIs in the Philippines. They’ve also been around for 30 years, proving that their loyalty to the mission statement isn’t some honeymoon start up phase.

On our second day in the office we learned the story of Emma, a now 50 year old woman who was one of NWTF’s first borrowers when the organization first developed in the late 80s. Back then, Emma found her and her family in a cycle of poverty, including one episode where she washed fried chicken from a trash can just to bring the family something different for dinner. After receiving her first loan, she opened up a small sari-sari store (think Filipino bodega). She was driven to make her business succeed. And when she did, she opened another: a piggery. And then a restaurant. And then real estate. Now, she rents out space to the main NWTF headquarters office. When advised to switch to a traditional bank with more lenient interest rates, she rebuffed: “When I was poor, no one wanted to give me a loan, except these guys.”

Underlining any mission statement is the question of purpose. In other words, “Why?” Why does your role exist at your company? When stock values and quarterly earnings are put aside, what is it that my company or organization serves a purpose for? The bottom line answer is rarely ever to simply grow revenue, increase user adoption, or bring in new leads.

I like digging underneath that cursory layer because it better helps me understand why an organization is designed as such. At NWTF, that means not only focusing on developing clients who can pay back their microfinance loans, but also on finding the patience to be with these young women as they learn the struggles of a start-up business in the hopes of growing out of poverty. 

Not included in this brief entry is a list of other lessons picked up from the journey. I'm going to start putting those takeaways into action right now (great to see you again, New York!).

On a recent trip to Brazil, in the heat of the World Cup and with tickets to three games myself, I found myself hardly believing that I'd ever have the opportunity to witness firsthand a moment in history just as unique. World Cup aside, Rio de Janeiro has plenty to hold you for weeks - Christ the Redeemer, Copacabana beach, churrascarias (steakhouses), and an endless line of clubs and block parties. Tack on the frenzied mayhem of the World Cup and your itinerary starts to look plump. 

Leave it up to the Brazilians to keep you stress free anyway. 

Two blocks off the shores of Ipanema, three friends of mine and myself found ourselves blowing through two volleyballs and one soccer ball in one week. Of the 30 or so hours we spent on the beach, only 2 of them were spent actually sitting down. We went to the same sandwich and juice bar - sometimes up to four times in one day. And on one celebratory birthday of mine, I woke up to an acai bowl with birthday candles emerging from the purple slush. 

We saw Colombian striker James Rodriguez score from outside the box, just eight rows back from the pitch. We watched France take Ecuador out of the tournament, and we witnessed Belgium's textbook excellence well before the US Men's National Team did. And when we weren't watching games at Maracana Stadium, we watched them in expat bars (long live Tio Sam), hotel televisions, and along the flanks of the beaches in crowds of uniformed tourists hunched over coconuts. 

---

In BJ Novak's short story collection One More Thing: Stories and Other Stories, he brings to the reader the character of a dead grandmother in Heaven who spends her time watching Frank Sinatra perform live each night. Novak's idea is to create a world with infinite time and then ask the reader what they would do with that infinite time.

The grandmother's response to this question:

"'It's funny, isn't it?' said Nana. 'You have infinite time here, and there are infinite things to do, but you still don't end up doing much of it. You do what you love most, over and over"

---

I don't have a particularly long list of places we visited or activities we did. In the end, we went to a handful of neighborhoods: Ipanema, Copacabana, Lapa, Santa Teresa, Gavea. We didn't even see Christ the Redeemer up close. I snapped one photo from the top of Sugarloaf Mountain and we drank in the streets of Gavea. 

The rest of the time, we we played beach volleyball and watched the World Cup. Over and over.