Sunday, January 27, 2013

Thoughts on turning 30, and a decade's aphorisms

10 years ago I was living at the abandoned, beer-spattered house of the Ultimate Frisbee team over winter break at Wake Forest University, having recently been kicked out of my parents' home for leaving the Jehovah's Witness faith. I read "The Fountainhead" and in Ayn Rand I found an author with a kindred spirit. I became an atheist Randian libertarian.

My isolated Jehovah's Witness upbringing left me unskilled at negotiating personal relationships. I expected the world to become my friend upon my emancipation and I was disappointed to find out how hard it would be to make friends. There is no doubt that I was/am weird and that weirdos have a hard time making friends. 

But my earnest naivety must have been endearing to some people. I made a few friends, fewer close ones, and went on my first dates. For the first and only time, I even briefly fell in love with a girl that loved me back.

I worked my way through college as a waiter at an Italian restaurant chain and by cold-emailing professors to ask for handyman work. (Once, I sold a Smashing Pumpkins box set so that I would have the money to take my first girlfriend on a date to IHOP. It was all the money I had. I didn't tell her that. I wanted to look cool.) I did not know where web pages came from. When I graduated with a degree in economics and mathematics, I spent a half-decade struggling to find a career and many hours thinking, reading, and writing.

(One of my more embarrassing business memories is standing outside of office buildings in Atlanta, handing out resumes to businessmen like they were some kind of concert flyer. I walked into the Atlanta Bain Consulting office unannounced with a box of chocolates and some resumes in a gift bag for the secretary. None of this worked to get me a job. I was clearly an outsider. I overcame any hard feelings towards Bain in time to vote for Romney in 2012.)

I started adult life in Atlanta with a few hundred bucks in my pocket. I didn't have a plan but it was a big city and I figured that I would find something to do. My car died and the repair took up all my money before I found a job so I was forced to work as a waiter again. In Atlanta I was most happy. I struggled professionally, but I was surrounded with wonderful people. They struggled too, but we helped each other out. My roommates and I hosted epic house parties and dinner parties. Our rent was under $350 a month (each) and nobody worked more than 40 hours a week. The possibility of love was everywhere, which eventually coalesced into a very real and very fateful girlfriend living in DC. 

The siren song of Paul Graham's essays on startups almost made me move out to Silicon Valley from Atlanta in 2006, but I was convinced by that girlfriend to accept a position in an investment bank in DC that her family had helped me obtain. With their help, I was an insider. Investment banking wasn't a good environment for me, so I left two years later to try that tech startup thing. First I went to grad school for Computer Science in San Diego, and then finally to ground zero of the internet revolution - Mountain View, Silicon Valley.

(I planned to work first and save up money at a lucrative programming job before starting a company but that didn't work out. I had no programming experience outside of grad school and I was an outsider all over again. I showed up to one interview in a business suit - a big faux pas in California. I didn't get the job. So I started a company instead.)

I'm skimming over 6 years here, but they were mostly a grind and not that interesting. Also, they relate to things that are still recent and relevant so I don't feel comfortable discussing them publicly. It suffices to say that they taught me the value of leisure and doing a job you enjoy, mostly by counter-example.

That said, 6 years of emphasis on career skills made a big positive difference in my professional life, even if my personal life has suffered from lack of time and attention. At 30, I feel confident moving in the world. I have far, far more business savvy than I used to and I know how to portray myself as an insider. I have real, marketable experience in technology and software.

I am looking forward to my thirties - the decade when many men come into the prime of their expertise and power. I have surrounded myself with effective, smart people and I hope I continue to grow more like them. I reconciled with my parents. I'm writing this post sitting on a couch at their house. I am visiting for a week to see my new little nephew who lives with my sister in the neighborhood. (later edit: he's a darling, by the way. Such a calm, happy child.)

I am no longer a Randian, though I still encourage others to read her works. I am still an atheist, but I appreciate my Christian cultural heritage. You can often find me in a church service of a denomination less insane than Jehovah's Witnesses - I find it enjoyable and thought-provoking. I am still mostly libertarian, but I am more interested in good governance than maintaining libertarian purity. As I am more interested in good living than in maintaining atheist purity.

As a philosophy, eudaimonia is its own reward. 

I see people 10 years older than me living how I'm living, and I know I don't want to be doing the same thing when I'm 40 - single, bouncing from job to job and city to city, trying to be cool, trying to meet women. Being cool is exhausting - I can't imagine trying to be cool for the rest of my life. The Christians have a good thing going on with their emphasis on family (other traditional cultures in the US do too, but they are mostly based on ethnicity and therefore closed off to me). Hedonism is for happiness in the short term, building things you're proud of is for happiness in the long term. A good life needs a balance of both.

The most disappointing lack of personal growth over the last ten years is that I am still fairly bad at  personal relationships. In some ways I may have regressed - any endearing naivety I may have had is long gone. I have little idea how other people experience the social world. I think that may be a part of a matrix of qualities that goes with skill at math, nerdiness, instinctive iconoclasm, and being genetic cousin to an autistic. Part of my New Year's resolution is to approach the problem with Silicon Valley gusto. What do people who are well-loved do that I don't? I don't believe that problems must remain unsolved forever. And a brief period of happiness in my past gives me confidence that I can reach that state again. 

Finally, I would like to close with some bits of wisdom that I have accumulated over the last 10 years. Some of these aphorisms may sound obvious, but they were big revelations for me.

  • People like to help other people. Ask for a hand from people that are where you want to be. They will gladly offer it.
  • You will be happier spending your money on experiences than spending it on objects.
  • There is little value in doing hard things just because they are hard and no shame in taking an easy path that leads somewhere useful.
  • Having that difficult conversation is a lot easier than avoiding it.
  • Every time I lost my temper I was given cause to regret it. 
  • Good advice is so valuable. Access to good advice explains a significant amount of the difference in experience between children of the rich and the poor. 
  • If you see something awesome, world-changing, or historic happening on the news then you can go be a part of that if you want. I am working at Coursera and advising the Thiel fellowship, how cool is that? I feel like I'm living in a movie.
  • Most groups of humans have some wisdom to offer - (traditional, radical, hippie, conservative, religious, atheist, ancient, modern).  Acknowledging this will make you popular with nobody.
  • I have learned a lot faster outside of school than in it. I also kick myself for studying the wrong things in school. The "real world" gives a powerful dose of perspective. 
  • The marketplace is a doocracy. The ability to produce something of quality is rare and highly valued. 
  • If you can't have a respectful and productive disagreement with someone, then your relationship is going to fall apart because disagreements WILL happen. This applies to every kind of venture.
  • Human relationships are often valued too lightly.
  • Personal virtue is undervalued.
  • Love lasts. Anger doesn't.
  • Humans are often irrational. Therefore, I am often irrational. Therefore, getting myself to do what I want is a difficult task. Self-management is an art which we are cursed to eternally perfect.
  • Fashion drives belief. Fashions arise in cohesive cultural groups. As smart people have separated into more distinct cultural groups, smart people also believe fashionable wrong ideas. 
  • RE: that last point - the western world is the most egalitarian, free, productive, and just society that humanity has ever produced. Global capitalism has reduced poverty to a smaller proportion of the globe than ever before. Technology is connecting humanity into one people. Our species has never had more cause for optimism. But these things are not fashionable to know or say.
  • There is always someone who will be famous for saying what is bad is good and that what is good is bad. Human nature has a streak of perversity. 
  • You can't convince someone directly of an idea that is radically different from the ideas they already hold. You have to meet them closer to their idea space and lead them away one step at a time towards another perspective.
  • The easiest way to become what you wish to become is surrounding yourself with people that you admire.
  • To get great at something, you must first be a beginner. 
  • My attitude on cultures is "by their fruits you will know them". I choose to adopt what is useful and I leave behind what is not. 
  • Fun is a necessity. Emotional well-being is a necessity. Neglect them for your career and your career will suffer. 
It is impossible to make a single judgement on any period as large as a decade. Each decade is full of every emotion with a name.  I bro-fived my teammates after a successful software launch, laid in bed crying for a full day, danced in the desert, held my sister's child, addressed tough interpersonal situations and shamefully avoided them, sat at home by myself on weekend nights, hosted some raging parties, started a successful meetup that is still going, punched people in a boxing ring, saw my name in the news, broke up with cofounders, spent my last dollar, read hundreds of books, was overwhelmed with awe and beauty, wrote bad poetry, wrote good poetry, flirted with beautiful people, held my tongue against people I intensely disliked, changed people's lives and minds, pissed people off, watched my father start his own business after the age of 60, vowed vengeance against religion, defended Christianity to a room full of atheists, learned the lyrics to Christmas songs at the age of 28, cried while driving away from a city with all my belongings in my car three separate times, and identified a dream job and made it happen exactly once. I count myself lucky for the experience of the last 10 years and I look forward to the next. I am eager to see where my story goes. 


  1. Jake - thank you so much for sharing this. I learned a lot. Lessons may seem obvious in hindsight but I understand what you mean when you said they were true revelations at one point. Your twenties sounded extremely challenging and productive. I'm sure there's a lot more and probably felt weird trying to sum it all up in a blog post. Let's get together sometime to talk about it!

    - Ricky

  2. I dont know how i got to reading this page, but im glad i did. Its been awhile since read something so sincere and honest. Something I can relate to.

  3. Good story. Thanks for sharing.