[A work in progress]



Life is a quest for meaning. As I look at my life thus far I divide it into chapters that reflect the meaning I have found in each stage.




A snowy day. An apartment. An alley. This is my first memory. It symbolizes for me now a world that is both menacing and aspirational. I have always loved the snow, and I realize now that it represents the human condition.

My mom home schools me for kindergarten, and I believe this helps me throughout my life to be more independent and creative. I care not for rules and existing social structures. I care to think brilliantly.




I develop a meaningful sense of accomplishment from the business events in which I compete. A highlight is ranking tenth nationally in the Marketing event in Future Business Leaders of America. This is the first time my acumen is affirmed by some powerful national organization, and it illustrates for me the immensity of my potential. This competitiveness has never left me, but I have tempered it with the realization that external approval is fickle.




I dream passionately of going to Wharton at Penn. It embodies the highest level of achievement, the opportunity to be the absolute best in the world. When I get the deferral letter, I am not totally surprised (I have been calculating the odds quite precisely), but my dream seems to be absolutely annihilated. There is an opportunity to follow up before they make the final decision, but I pursue it half-heartedly. I have already decided I will not make it there. And the rejection comes several months later. Looking back, I long for the intellectual opportunities the Ivy League presents, while cognizant of the fact that Penn has elitist strains and that business is not at all my calling.

USC provides a diminished but appealing alternative. It's a financially difficult proposition, but I hope and believe strongly that it will get me out of the parochialism by which I seem to be surrounded. And I idealize a life of glamor. I view it most of all as an investment. And it pays into a belief at the time that it would be wrong to attend a public school, subsidized by tax dollars. (I thankfully go on to reverse this position when I realize the power of state-sponsored institutions to equalize opportunity and to facilitate genuine improvement to society).



The beginning of college is the most remarkable period thus far in my social life. I bring myself to meet a multitude of people. It's in this time that I summon the extraversion that is just a much a part of me as anything else. There's absolutely nothing stopping me from embracing this opportunity.

I have more fun that first semester than I ever have, and experience the social life that I never previously have had the friends to experience with, nor the idea of where to find, nor the belief that it is worth pursuing. It means allowing a degree of hedonism.

It means finding love in football. Never a passion of mine before, the group atmosphere provides a sense of belonging. At a school where my worldview doesn't mesh with those of my peers, we can bond over something primal and ecstatic. For one of the games I convince my good friend to paint one another's faces. And for a later game I convince two to paint our chests. I do wild things because I can, and because I am tired of putting limits on myself. I am done being hemmed in by external circumstances.

I find myself reevaluating my political beliefs. With my first-ever vote, I strongly support the 2010 Republican takeover. As I watch CNN that night in the lobby of my dorm, I eagerly anticipate the reversal. It turns out to be a disastrously harmful election, but I am glad I fully embrace the conservative worldview. I am glad I try it out. Experimentation becomes more and more a part of my character as I progress through college.

And yet, I take enormous pride in attending the rally for President Obama's reëlection. It is an honor and although I don't agree with much of what he says, it humanizes him.

My moral priorities shift. College tends to liberalize (and liberate) a person, and the influence of my living mates plays a large role. The moral code of an all-male college dorm is disconnected from the traditional one our society at large pushes. It is less intense and forbidding, more open, and loads more fun. And it teaches me that being a good person has quite little to do with your sexual life or the other secondary things on which our society tends to focus. Our discussions allow me to reorient existing beliefs that I thought I would never reconsider. And they set me up for a more open-ended and expansive spiritual worldview. The group is not religious. They point me to a music download site, and I find myself thrilled both with the possibility of getting any song for free, and the fact that our society considers it a taboo. I realize that paying or not paying for music matters very little, and that I am not doing anything I find deeply wrong. It is not worth moralizing strongly about.

More than any class previous or since, "Knowledge, Explanation, and the Cosmos" busts open my worldview. We explore broadly metaphysical topics including the existence of God and epistemology. The latter plants the captivating and empowering idea that no fact is conclusive and that reality may be entirely artificial. This is exactly the mindset required to create new knowledge and to challenge convention. It helps me develop a more critical attitude to existing approaches and structures.

USC never feels quite right, though. From my first week on campus I experience a profound sense that me and my peers approach the world, and our studies, from vastly different perspectives. A discover a powerful and compelling intellectualism that contrasts with the practicality, and often superficiality and hedonism, of the people around me. These perspectives are irreconcilable, because where I want intensity they want relaxation. Where I thirst for knowledge they seek application.

This disconnect upsets me, and I dedicate myself to making a better life for myself, the same way an immigrant would. I have in mind from the first week of classes, when that realization hits me so powerfully, a plan to transfer. Penn is still at the top of my list. I focus on excelling in my classes, and grow fond for the library and late nights. After the most careful and thorough work in my life I earn a 4.0 that first semester.




My first quarter at a new school brings back much of the thrill of starting college. In particular, the change in scenery prompts me to start meeting people again. I meet people through apps. I meet quite few. And quite a few treat me quite poorly, with all manner of passive aggressive behaviors, and my self-esteem takes a blow.

During the first half of my second half of college, I connect particularly with a friend I knew obliquely from high school (or more like, he knew me). We develop a familiarity and humor that feels easy. It is a pure friendship and a pure romance. The emotional intimacy does throw me off. It is uncomfortable. I make it about his appearance (which is really a red herring). And so I abruptly cut it off. If there is one person about whom I wonder what could have been, it is him.

As graduation nears and I have less busy of a social life, I find more sophisticated ways of looking at the world. I intensify my reading of the New York Times and get into others like the New Yorker. I take in as much social commentary as I can, and in turn develop my critical thinking and writing skills. I learn to look at situations with a more skeptical eye, and to not take for granted existing power structures. I get a few letters to the editor published, and seeing every careful word reproduced is gratifying.

I develop a passion for game collecting. I start with a few titles I remember and expand into past generations and the games I had never gotten around to.

Anxiety about my health plays a large role in my last year of college. I experience a couple of what one could call concussions (although a medical diagnosis is difficult). Because experts know so little about the topic (particularly diagnosis and long-term effects), I am left in a state of confusion.

I respect and admire Andrew Kim as a visionary designer. Him choosing Microsoft is a major reason I choose Microsoft, and his project redesigning Microsoft resonates with me as something I would do. I see no ceilings to my ambitions and believe that an individual of any age, class, or title can and should solve massive problems. The salary is fantastic, it is a well-respected company, and most importantly I see it as a place that is changing, becoming more innovative and freewheeling. It also seems to respect design much more than it has. I see potential for myself, the company, and the product I work on.





The essence of human relationships is fit. There is an imperceptible quality between two people.

Where the fit is strong, there is a magical je ne sais quoi to every moment. Where there is no fit, a sense of apathy pervades our interactions and thoughts toward one another. Where the fit is antagonistic, proximity and time together actively antagonize a person until they are able to compartmentalize those feelings.

Fit derives on some level from overlap in interests, and in more meaningful relationships from shared passions and worldview. And yet we can generally gauge fit in a matter of seconds, based on a first impression. This may be a purely superficial approach but it is also reality. It may be that our external communication (whether by appearance or conversing) reflects our inner state — that the eyes are a window to the soul. This does not excuse a person from making a meaningful attempt to relate to one another, something we can always do and usually should.


Because the experience of working at an organization is largely defined by the human relationships we make (voluntarily or not), we can understand fit in terms of our coworkers. In my case, I found myself surrounded by people with a fundamentally different worldview.

I commend them for their maturity, and appreciate their willingness to accommodate the way we spend our time outside of work. Hours are entirely reasonable, benefits are decent, and there is always opportunity to go to the doctor or care for a kid, without judgment from peers.

Where we see differently is the scale of our ambition. My coworkers take a focused local approach, and I take an expansive global one.

My ambitions for many years have been soaring and universal. I dream in younger years of converting the U.S. to the metric system. And in a personal project I put together after my first weekend at the company, I envision a suite of Microsoft web sites that is unified and beautiful. It is a reflection of universal thinking that bridges traditional organizational boundaries and internal politics.

I focus, to paraphrase an Apple ad, on how our work will make someone feel. My coworkers think in terms of concrete achievements, defined by exacting measurements. (The company-wide performance review and rewards system, as well as the organizational structure writ large, orients itself toward this approach).

The work I am doing, focused on internal tools and processes for customer support, does not correspond with my passions. It has little direct impact on the end user. And it involves very little design (designing processes notwithstanding). I am not exercising my passions, although I do spend personal time learning about design, and take up blogging as well. The human spirit is persistent and cannot be extinguished, and I find ways to remain sane.

The bigger issue is that managers do not encourage people in my junior position to engage in and follow through on big-picture thinking. I do have a most delightful opportunity to share my work internally with others who appreciate and embrace it. It is nice to know that someone is paying attention, and see the world in a similar way.

All things considered, I am remarkably fortunate to pay off my student loans. Even better, I spend that time growing in my taste for design.

Knowing what does not work for you is a powerful way to redirect your energies to what does.


I experience what one might or might not call a concussion a few months before ending my time at Microsoft, and the symptoms linger for many months. In a mutually destructive combination, the headaches and fatigue make it difficult to focus on work, and my lack of passion for my job saps my energy and exacerbates the symptoms. It is a neat illustration of the relationship between mind and body.

This accident leads me to feel that I have lost agency; that I am somehow being punished for misdeeds. While I do not believe that God does or would tend to focus on punishment, the desperate search for an explanation leads me to this speculation.


I am fortunate to have a roommate, also at Microsoft, with an appreciation for philosophical discussion. We spend late nights debating a variety of topics, and we generally disagree. In the one that most starkly illustrates our different worldviews, we battle over the merits of intuition and reason. We land on different sides and engage in a debate I find distressing because of the cognitive dissonance I experience. I find value in his perspective and agree with it on some level. I am also resistant to the idea of technocracy, of a world ruled by engineers. The internal conflict leads me to reconcile the two and write a blog post about it. I tend to seek compromise, and successfully find it here. In future debates I actively seek ways for us to agree, and learn some persuasion. I open and change his mind on one topic, and this makes the exhausting enterprise feel more worthwhile.





Our environment matters, shaping how we think and act. New York is vast — in the kinds of people, the kinds of places, and the kinds of experiences we can have.


Just before I leave, Hillary Clinton announces her campaign, and with that introductory video I fall in love. I realize how much she can do to lift up the middle class and disadvantaged groups. She is a strong woman and a great role model, coming back from every defeat and each attack stronger, becoming more resilient and outspoken with every person who tries to knock her down. She refuses to sit down or shut up. So it is incredibly fortuitous that she schedules her campaign kickoff rally for just after my arrival, and in New York — she knows!

By this point in my life I have seen enough of high-minded idealism to know that movements like Occupy Wall Street mean nothing when loosely-organized and without clear demands. Hillary has the experience, electability, and realistic attitude to push through legislation.

As I hop around from neighborhood to neighborhood, I recall the thrill of traveling through China, Japan, and Europe. I realize that the nomadic, unsettled lifestyle appeals to me more than a complacent life. It challenges me, allowing me to prove to myself my resilience. It is full of stimuli that provide for great photos and open my mind to alternative ways of living and thinking.

I come here with savings from my time at Microsoft, but certainly nothing like a trust fund. The trouble with living in the city is how to pay for it. We sacrifice because we know the opportunity and inspiration here is greater than in most places. A designer will live here because they know how much around them can trigger new ways of thinking.

With the subway a part of my daily life, I develop railfan tendencies. I catch one of the few remaining railfan windows, on the J train. And I have the distinct pleasure of being on the first car of the first train to the 34th Street–Hudson Yards Station.



More about me (to be announced 1 / 1 / 2016)