Looking Back: 2016

2016 has been my most important year in almost a decade. I've had epiphanies, perpetrated some crucial failures, earned a few new friends, and redefined my personal goals in life. It has been nothing short of a total turn-around for me—a pivot from a flatline I didn't even know I was tracing to a sharply upward direction.

Here are a few of the important nuggets:

The Operations Institute

I began the year speeding off at 110mph toward The Operations Institute. I was so convinced it was my future that I made a big fanfare about it, sent out emails, updated titles on my profiles, and printed business cards.

In fact, it was not it. I spent about 6 months actively developing ideas and materials for the project—a body of work which constitutes a beginning that I'm still fairly proud of—and then slowly realized that I had spent the last 8 years of my life eschewing the important connections and opportunties that might otherwise have laid the foundations for its success. In short, rather than building a foundation of close friends and collaborators who knew me and trusted my abilities, I had maintained a distant network of connections whom I had spent a few evenings with by a fire somewhere. Rather than hone my skills on real, productive projects among colleagues who could help me develop, I had instead refused to commit to anything long enough for it contribute significantly to my skill set.

The failure of the Operations Institute (for now) laid bare what I needed to work on to create success in the future: I needed real, hard skills, and I needed to use those skills to earn the company of some particularly extraordinary fellow humans. Back to school....

A Social Life

Even before I really started to ramp up my efforts with the Operations Institute, I realized that I would be hindered by my lack of connections. So as soon as I moved up to Chicago in late March, I began to build a social scene. The problem was that I'd never actually done that before....

I had this hilarious moment at a certain point in late Spring when I realized that I didn't know what a friendship looked like (much less a romantic relationship). I had spent so much of my life completely alone—I was so comfortable alone, and in fact so exquisitely happy alone—that there wasn't any internal pressure pushing me to experiment with interacting with people in different ways. "Friends" to me were people whom I would have dinner with every once in a while in a sort of robotic gesture of recognition.

So, in the absence of knowledge about how it should work, I resorted to experimentation. I began to say yes to virtually every social opportunity I could find. I sought them constantly (it was even on my to-do list once a week for many months). I was on Meetup.com, EventBrite, OkCupid.... And—much to my astonishment—I was actually kind of successful! By the end of October, between volunteering, dating and general socializing, I was so thoroughly worn out (and behind on my deadlines) that I had to declare a moratorium on all social activities during November.


Dating deserves a special mention here. This year I had what was effectively my first real date ever. I think to most 30-year-olds, this sounds crazy. But all two of the functional relationships that I've had in my life have begun in shared living environments. (Ridiculous, right??)

So I finally got on OKCupid, and soon after that I gained the confidence to start actually talking to girls in the real world, too (!!). Granted, of the various dates I had this year, few were particularly exciting, but it was exciting to think that I was finally breaking out of the shell I hadn't even realized I was living in!

New Goals

Another interesting development this year was a revamp of my personal life goals.

The most important change was that I generalized my ambitions and I grounded them in a physical (rather than theoretical) vision of my future. When I envisioned my phyiscal life in 20 years, for example, it included a family, and that family had a home. Thus, I couldn't ignore that I would need to start saving some money to buy at least the materials and land with which to create a home, and to save money, I had to have a job with a wage that was more than break-even.

The other big change in my goals was the formal recognition of programming as a medium for my ambitions. Ever since I started programming, I've seen it as a sort of playground of the privileged. I recognized its immense power, but because it was fun for me, I never felt I deserved to do it as a full-time occupation. Now, I recognize that it's all I ever end up doing anyway, so to continue to run away from it is totally pointless.

Thus, I've established the 20-year goal of either leading or contributing significantly to the development of at least one important piece of open-source software. (My personal goals file isn't very interesting, but it's here if you'd like to see it. I update this quarterly.)


Perhaps the most important lesson that I learned this year was the value of risk. Entrepreneurs are told to "stay hungry", people tell us that risk brings reward, etc., but, while I understood those words, I didn't understand the concepts behind them. I'm planning to write a longer post on this subject, so suffice it to say that this was a valuable lesson gained this year.

Brooke Allen

The last important thing that happened to me this year was Brooke Allen.

Late in the summer, I had a strange encounter. A man contacted me on Couchsurfing, not requesting to stay but offering to treat Reed and me to dinner. He looked like the dopey dad type—paternal, moralizing, but loving and well-intentioned. His story was interesting: an ex-hedgefund manager with a bent for systems and programming, now devoted to what looked like just running around and doing good. This was Brooke Allen. Reed was busy, but I agreed to meet.

By the end of the night, we had talked extensively on a wide array of subjects, but we had centered on me. What was I doing with myself? Where was I going? What did I want to do? Most importantly, what had I done up to now?

This last question was the kicker. I floundered, struggled to produce an answer, then gave in. In 5 short hours, I had been treated to a delicious Thai dinner, talked casually about the dynamics of the Couchsurfing community, and then had been totally called out on the stagnation of my last 5 years. This was in August, when I was considering going back to school for the Bachelors Degree I never earned. Brooke, a staunch proponent of work experience over formal schooling, argued effectively that school could only further delay solutions to my productivity problem, and that I really needed to get to work.

Thus, I decided that I would go back to work in January, and that there was lots of prep to do!

Other Things

Some honorable mentions:

  • Activism—while I can't claim a single important political action this year, I have started to scratch the surface. As I explored ways to support the Black Lives Matter Movement, I've had to become more active on Facebook, and I've begun to map the process of converting from a slactivist to an activist—something that requires considerable time, humility and tact, especially when the movement is not your own.
  • Reading—I've always appreciated reading, but I've rarely given it a dedicated space in my life. This year, however, I faced the facts: My personal advancement depends on the consumption of a very serious number of pages per year. In light of this, I've begun to mark off two hours per night for reading. I don't always hit it, but I'm past the hump.
  • Skel—Skel is the framework that I created and on top of which I built this website. It was (and still is) a huge adventure and a precarious experiment, but whether I ditch it or move forward with it, it was an absolutely fascinating attempt to build an innovative application framework from scratch, and I learned a ton doing it. (Read more about it here.)

Looking Forward

Yes, 2016 has been a doozy. I'm coming out of it with very few victories, but feeling supercharged by what I've learned from my defeats. I'm eager to start 2017, if a little apprehensive about the task at hand. Still, though, if 2017 is half as valuable as 2016, it'll be a good year!