What do you optimize for?

Advice depends on context, assumptions, and what you’re trying to optimize for. Much of it boils down to “this is what worked for me so take it with a grain of salt and try to calibrate it for you.” Useful advice either tries to account for differences between people or include generalizable principles for how you should think about something.

People will try to make these adjustments doing something  like “focus on what you like the most and are best at.” Although I think that spirit is right, it frames the problem in a counterproductive way. “Focus” is often understood as “follow a set plan towards this goal and do what you think you should be doing to succeed.”

I think this is the wrong type of optimization.

There are two things I optimize for which I’d like to explore here: interestingness and serendipity.

First, “interesting.” You may have noticed that what’s interesting to you has changed over time. Why is that? Keep in mind that interests are distinct from talents. Do interests change for the same reason that mathematically-inclined minds tend to be interested in formal logic but not painting, while artistically-inclined minds tend to be interested in Broadway but not software engineering? Is what we’re generally curious about related to things that give us happy fulfilling lives?

My take on this is that “interesting” is a heuristic for all of the things we need: usefulness, novelty, personal fulfillment, etc. Not only do interests change over time, we seem to jump between intense focuses and binge something until we suddenly stop caring about it. Our brains need some way to choose what to learn about. This idea has been studied in a more in-depth and rigorous way than I’ll argue here — check out this paper for instance.

You can probably relate to this real life anecdote: in high-pressure situations, I’m intensely interested in specific problem-related information and career-focused things like how to deploy code with Docker to save me time. It’s critical to note that I’m genuinely interested in that sort of stuff and I don’t explore it for external reasons. I’m just inexplicably more curious in that moment. When I have more free-time and no responsibilities, however, I find myself thinking much more about food, politics, my next workout, philosophy, music, or stand-up comedy. All things that don’t accomplish any specific goal but still enrich me as a person (a fact my humanities professors are always so ready to remind me of!)

The point is, interests aren’t just a luxury. They serve a useful purpose that you should consciously consider when organizing your life.

Second, “serendipity.” This is a major theme of Reid Hoffman’s The Startup of You  and Marc Andreessen’s career guide. The thinking is that breakthrough opportunities usually present themselves through random chance. Maybe you happen to stumble across the right problem at the right time and think “hmm, why hasn’t anyone solved it this other way?” or your friends decide to go to Denny’s at 3am to discuss a business idea. Seemingly small and innocuous moments lead to truly exciting opportunities.

I’ve already directly observed this in my own limited experience. I attribute pretty much every major success of mine to pure luck (with the prerequisite of hard work pouncing on an opportunity when I see it):

  • 100k-download Android app: I spent months toying around with different programming tools and just happened to stumble upon a great tutorial and project idea I liked. I also randomly played around with a bunch of different marketing techniques for fun.  Only one of many happened to stick and things just naturally snowballed from there. It was a low-quality app that I happened kill it because I had failed at plenty of other projects before it.
  • College: originally I could only see myself at a some “elite coastal school” (staying in the Midwest, I’ve since been telling myself it’s more like “coastal-elite school.” Hah!) but luckily I decided to serendipitously apply to a bunch of schools I didn’t really care about. If I didn’t go out of my way to stir some up random luck, I wouldn’t have gotten an offer from UIUC that put me in a top CS program and saved my a quarter-million in tuition over my next-choice option.
  • Contrary Capital: I randomly saw a Facebook post and decided to make a cold email.  If I hadn’t been on my phone that night or if I hadn’t decided to spontaneously email the founder, I wouldn’t have gotten the amazing and humbling chance to help lead a venture fund.
  • Friends: My sophomore year I went on a trip to Silicon Valley organized by my school. I wasn’t super excited and had actually turned down the chance to go the year before, but I decided I could use a little more serendipity in my life. There I made a great friend. Through her, I made some more friends. One of them became my roommate. He introduced me to many other cool people. Again, the original trip was just serendipity at work — there was no goal or process involved, but super valuable relationships grew out of it.

I’m sure everyone has similar stories of pure chance turning into something incredibly meaningful. Yet most people would probably have taken the above examples and focused on some sort of process or execution that made the most of the opportunities.

Think of it this way: we spend most of our lives doing things. Working towards goals. Learning. Talking. We do a great job of carrying out whatever it is that we’re trying to optimize for. We really don’t give ourselves enough credit. These two heuristics help you broaden the opportunities you come across and choose which ones matter most. That’s at least half the challenge — the rest comes naturally.