play the most interesting move

My “previous assumption”, for the last five years, has been that I would go to grad school, become a professor, and live happily ever after being paid to indulge my curiosity and teach.

Grad school, however, has been agony. My first year was miserable and fairly unproductive. Before grad school, I took one year off the academic track to live in San Francisco, and I loved it. Not only was my life filled with wonderful adventures, I made far more money than ever before. Coming back to the Bay Area for winter break and a short vacation, I got back to my old self and enjoyed life again.

Abandoning grad school to move back to San Francisco is starting to sound like an interesting move. I don’t feel a strong impulse to make this jump right now, though. I want to percolate for a while.

Negative At this point in my life, if I quit grad school, that would end my chances of becoming a professor. Indiana has a great cog sci program, so I’d be losing an extraordinary opportunity to become a cog sci/comp sci researcher. The one thing I have learned most while in school has been math; stopping grad school would likely put a stop to my continuing to learn much math.

Positive I can make good money working in software. Now I even know how to do that right: alternate between working contract jobs and working on my own projects. I love the city and feed off its energy. I have lots of ideas—for products, for web sites, for books. I have extraordinary friends in the city who introduce me to wonderful things. The biggest positive is just that I could focus all-out on one project at a time. Even when working contract jobs, I would still have energy left to work on projects and have memorable weekends.

One thing I know from past interesting moves, from Go and improv to real life, is that they require a peculiar, extreme form of commitment. You have to be completely committed to making the new situation work out, but have no fixed ideas about what form that will take. You dive in, and you become very open to opportunities as they arise. You accept instability and the need to improvise continuously. This can’t be done tentatively.

Also, when you make an interesting move, you should have a sense that even though things are very uncertain, you are moving into fertile ground—that the deck is stacked in your favor, even though the cards are unknown. The John McCain style of “just fly into enemy territory and trust your luck” is merely suicidal, not interesting.

I was going out of my head playing homework whack-a-mole. Hurry to finish the homework for one class. Oops, that took so much time, I haven’t even started the homework for another class. OK, hurry up and do that. Oops, the third class’s homework is already late and I haven’t started it. And I still need to correct homework for the class I’m teaching. And the cycle continues. Result: Spending all of my time in a brain-scrambled state, not really getting anything from doing the homework. (And the homework in the classes I’m taking is quite well-designed. It’s not the usual meaningless busy-work.)

Last week, I decided to stop all homework until I felt good. No homework while brain-scrambled. If I have to take a zero on the homework, so be it. If I have to fail all my classes and drop out of grad school, so be it. Working in a brain-scrambled state is no way to live. So I played disc golf in the afternoon instead of doing homework.

After two days of this, I felt good again. I did my real analysis homework in about six hours, and did it thoughtfully.

In Go, the object is to take the most territory (space on the board) for yourself. A principle that is commonly taught is: “Always play the biggest move.” The “biggest move” is the one that shifts the balance of territory the furthest in your favor (by reducing your opponent’s territory and/or increasing your own). Like duh, of course you should always play the biggest move, right?

Wrong. A crazy Australian friend of mine told me a much better principle when we played Go at Park House in San Diego: Play the most interesting move.

This is the move that throws previous assumptions about who owned what into doubt, and opens up new and unpredictable possibilities. The most interesting move makes the game more richly interconnected, less certain, and more…interesting. The kind of structure that your pieces make when you play interesting moves is less knowable than when you play safe moves, but also more resilient and adaptive.

The truth is, “play the biggest move” is a vacuous principle in practice. To apply that principle assumes that you can tell what the biggest move is—that is, that you understand the situation so thoroughly that you can actually know the future implications of every move. In a real game, you are always up against the fact that most of the game is unpredictable. What you can sense, though, is the moves that steer the game outside of its present course and open up new possibilities for interconnection, even though you can’t tell exactly how those possibilities will play out.

Real life is the same way, of course.

So, I’m making this a goal of the sort that I never complete, but execute continuously. As of today, this is my #1 guiding heuristic in life.