This week I was asked by a good friend, Michael LeGrand, “What is it like to have never had a 9-5 job?”

It’s true…I have never had a regular 9-5 job. I dropped out of school to play chess at the age of 19, I quickly won a chess fellowship that paid me $32,000 per year to play chess. I gave a few chess lessons in NYC to make money for living expenses (never more than 2 hours of work per day) and eventually discovered poker, at which I became pretty good at and made plenty of money without working very much. The more detailed story of how all of this came about might be a good topic for a future blog post.

There are certain aspects of my alternative lifestyle that make me feel like a bit of a spoiled child, but I’ve gotten away with them for long enough. For example:

1. I function horribly without proper sleep

So many people talk about how they haven’t slept more than 6 hours in a week. If I don’t sleep six hours in a single day I’m basically a shell of myself. I can’t focus, I can’t write, can’t play chess well and feel horrible when I try to workout. I’m basically a walking disaster. However I also have the freedom in my schedule to nap at pretty much anytime. So on those rare occasions that I don’t sleep a lot, I’ll end up napping for 30-60 minutes as quickly as possible and everything ends up okay.

The reason I’m so messed up is because I’ve never really had to regulate my sleeping habits, at least not since I was in college. I almost never have to experience the feeling of being exhausted and therefore I have very little tolerance for it.

2. I can’t stand people telling me what to do

Every now and then I get involved in small business settings with people, and every now and then these people try in some small way to exert some control over me. Recently I was told that “you are required to do XXXX”, when XXXX was not something that was ever discussed in advance. There is a certain tone that’s probably normal in some work environments, that I’ve never had to deal with and I’m not willing to work with people who use it. If someone thinks that because they pay me money from time to time, they can start bossing me around, then it’s just not going to work very well.

Let me share a story which in retrospect is completely absurd:

I was maybe 22 years old at the time, and was working for Chess in the Schools in NYC. I would go to the National Championships with them and coach the top high school kids in the program. I was paid for the trip but made a strange request each time. There are games each day at 9 am, 2pm and sometimes 7 pm. I made it pretty clear in advance that I don’t wake up in the morning, so they shouldn’t expect me to be there until around 11pm to noon, and so therefore I’d like to take those rounds off (there were other coaches there who would help too).

Maybe this request is so unlike anything they’d ever heard before, but for whatever reason they allowed me to do this for two years without any issues. The following year before the tournament I received a phone call from a very nice guy who worked for CIS, basically telling me that he understands that I don’t like to get up early, but that it would be best if I found a way to do so for these two days. Because he is an extremely reasonable person and because I honestly enjoyed working with the kids, I eventually agreed to his terms.

I’m sure if they just had this same talk with me in the previous years I would have agreed also, but I think I intuitively learned that if you just ask for something right from the start, that a lot of the time people will just give it to you. Ask for every single thing you want right at the outset of any negotiations, because it’s going to be a lot harder to get it later on.

3. I suck at doing things I don’t want to do



The idea of having to go to the post office to pick up a package is so infuriating to me that I’ll generally just tell the Post Office to return whatever it is to the sender.

When I was a pro poker player I worked for about 2-2.5 hours per day maximum. I could easily have worked 6-8 hours a day and made 3x the amount of money. But I didn’t really like sitting in front of a computer screen clicking buttons for 8 hours a day, so I didn’t do it and just became happy with the amount of money I did make, while giving myself 22 hours in the day to do whatever else I wanted to do. If I didn’t have this time, I’m sure I wouldn’t have founded the U.S. Chess School, which is now an official 501C3 organization!

I love chess. I love studying it and I love playing it. However I have a very hard time playing in major chess tournaments. A major chess tournament in the United States is basically an experiment put on by chess organizers to find out just how much they can torture a human being in a span of five days. You can’t sleep, eat or exercise in any halfway normal fashion during these tournaments and the games last way too long (the average game length should be cut in half).

I am aware that some of what I say above may be infuriating to the average reader for many reasons. My apologies, I’m just answering the question as honestly as I can.