Teachers insisted that I prove that I had been keeping up with the official curriculum.

Obviously, I hadn’t. But I was willing to step up to the blackboard and give it a shot.

Trying to reverse engineer math formulas on the fly with everyone watching me was unnerving. And the teachers weren’t exactly supportive.

So I’d invariably be sent to the Principal’s office. I guess the big lesson I learned was that grade school is not a place where they encourage you to figure things out on your own.

When I got to college I majored in Philosophy. This puzzled my friends who deemed this choice to be highly impractical.

To me, it was incredibly practical, but (apparently) not in a way that most people could understand.

Studying the great philosophers helped me learn to think better in many dimensions.

Of course, philosophy is just one path. The key thing is mostly learning to think for yourself, and not relying on “conventional wisdom.”

As Bill Walsh, the famous football coach, famously observed: “when everyone thinks the same, nobody’s thinking.”

After college, I wasn’t sure where to go next. I just knew that I wanted to avoid mindless conformity.

I spent a few years working as a waiter at an upscale New Orleans restaurant. It was incredibly interesting, and I learned many valuable lessons not taught in school (i.e. how to use psychology to increase the odds of getting a good tip).

But waiting tables didn’t seem like a good long-term career.

So I started thinking about how to get a better job, where (ideally) I’d get paid to think critically. Or, even better, challenge the mindless status quo.

I thought that was what lawyers did, so I applied to law school.