I’m 38 Years Old and I’ve Never Had a Job

I never have and never will have a job. Maybe it’s because I’m unbelievably lazy, or maybe because from the time I was young I put an extremely high value on my time, but ever since I graduated high school it was clear that I thought about things a lot differently than most people.

Before I go on I need to preface this by saying that I was in a much more fortunate position than most. My parents had plenty of money and were extremely supportive. If I was ever broke I knew I wouldn’t be begging for change on the streets. I could go on about the different types of privilege I have and have had, but that’s probably a completely separate blog, and I understand that not everyone will be able to follow my path.

Most people in high school have some vision of what they want to be. I had no vision. I never was once able to even imagine having a job. The idea of being a teacher, lawyer, or any person who had to show up somewhere in the morning and stay at that place all day never once entered my head. I’m not sure how my impressionable young brain managed to dodge the constant messages that society sends that tell you that “you are supposed to get a job and become a productive member of society”, but somehow it did. I literally never once, including when I was in college, envisioned myself doing anything in the professional world. I knew it was something people did, but the whole concept didn’t make sense to me.

For some reason I went to college for two years and even did pretty well, but eventually realized it was a waste of time and I dropped out to move to New York to “follow my dreams” and play chess. This was the one time in my life when I really had to worry about money. My favorite memory is winning a chess tournament for $200 and being so excited that I could finally afford to splurge and buy a $20 Carvel Ice Cream Cake. Eventually I got some jobs teaching chess, and I worked about 8 hours a week, making $40-$60 an hour (for a 19 year old in 1997, that was a lot of money). That was all I needed, so I had no desire or incentive to look for more lessons.

This last sentence is the key to everything. While most people who could be capable of earning that money would look for more and more opportunities to give chess lessons, I had absolutely no interest. I wanted to work a little bit, make a little bit of money, and then go on doing whatever the hell I wanted the rest of the time. I’ve noticed that this quality is extremely rare, and I feel pretty fortunate that it has been my approach in life.

One of the main goals of moving to New York was to work hard to win something called the “Samford Fellowship”. This is a Scholarship given to the “most promising young chessplayer in the United States”, in which they pay you a bunch of money (about $32,000 a year for two years) to just play chess all the time. Miraculously I won the Fellowship, and my lifestyle of never having a job was completely safe for the next two years.

Sometime while I had the Fellowship, when I should have been studying chess 24/7, I got into poker. I spent a decent amount of time playing, and while I wasn’t THAT good, I was building the skills that would put me ahead of the curve once Online Poker took off. I spent the first year or so of the Online Poker Boom being a small winner, but nothing too spectacular. However after a little bit something clicked, and it got to the point where I could basically print money.

Once again my philosophy reigned supreme. The large majority of poker players who I talked and played with spent maybe 6-12 hours per day, every day, playing poker. They wanted to make the absolute maximum amount of money. I on the other hand was very careful with how much I played. I allowed myself to work 2.5-3 hours per day, and this was pretty much my regular schedule throughout my entire poker career. Once those 3 hours hit, regardless of whether I was up a ton of money, or getting completely crushed, I would stop.

My poker friends warned me “Hey Greg, you realize this isn’t going to last forever, people are going to get better, the government might crack down, etc etc blah blah”. While I had my doubts, my friends were all completely right, as the days when I could make money with minimal effort eventually dissapeared. I could have easily made 3-4x as much money as I did by simply playing poker all the time during those golden years. However during that time I also used my free time to do the following:

1. I created a weekly chess tournament in New York City called the New York Masters, which became well known around the world.
2. I created the U.S. Chess League, which has recently morphed into the PRO Chess League, in which many of the top players in the world competed this year
3. I created the U.S. Chess School, which has run 40 camps in ten years to some of the top talents in United States Chess

There are probably lots of other little things I did during that time that I would have never done if I just played poker all the time. Maybe I would have more money in that case, but would my life be better? I strongly suspect the answer is no, especially since I easily have more than enough money now. My life would honestly not change if I had twice as much money as I do now, nor would it change if I had half as much money as I do now.

A fundamental question I often asked myself was: “Would it be a big deal if you lost half your money overnight?”, meaning, would it drastically affect my lifestyle. The answer was usually “no”. When the answer to that question is no, and it would take me years of inactivity for that money to slowly dwindle away, it became hard for me to see why I should work more than I wanted to. In fact it required serious discipline on my part to work the 2.5-3 hours per day that I did, and I probably only went 2 years where I was able to stay consistent with that. Near the end of online poker I was working an hour here, taking a day or two off there, and so on. But none of this mattered because it was obvious that I didn’t need to work. I was also in an extremely enviable position because at any time I could just decide to become a professional chess teacher, charge pretty high rates, and get plenty of work. *Note to parents* If your kid is really good at chess and not that interested in school, you should realize that being a professional chess player is actually an amazing job, and that your extremely young child has more immediately marketable skills than nearly anyone her age.

Eventually Online Poker ended (meaning that it became very difficult to play in the United States), and I originally planned to keep playing by using some kind of VPN setup. I had already planned a month long trip to Europe (something that’s really easy to do when you work whenever you want to), and during my month of traveling I managed to score a few chess lessons back in Philadelphia (don’t worry, just about 4-6 hours worth per week) and decided that I’d just not play poker for a bit. I figured I could probably go 3-5 years without working at all, and be completely fine, so why worry about it.

Another key point needs to be made about the idea of “going 3-5 years without working at all”. I hear a lot of people talk about how one million dollars isn’t nearly enough to retire on. These people are all idiots. If you have a million dollars or even anywhere close to it, and you have no children, you are unbelievably filthy rich. The idea that you will literally never earn any more money for the rest of your life, simply because you are “retired” or don’t have a regular job, is ridiculous. You’ll make some money here and there, enough to keep you afloat as you sit around watching your million dollars in index funds grow slightly every year. In fact if you invest it all and it makes 4% per year, that’s $40,000 right there. Then if you do maybe a few part time odd jobs that you enjoy, you have easily made enough money, without waking up for someone else at 7 AM every single weekday. Even if you lose 5% of your money per year, you’re going to be fine for a very long time. Maybe once your net worth gets down to $200,000 or $300,000, you can start worrying about what to do, but unless you are extremely irresponsible or experience some catastrophe, that’s going to take a very very long time. In the meantime just chill out, have fun, travel, enjoy life, don’t throw all your money away like an idiot, and you probably will never really have to work again.

There are so many people I know who are so much richer than they realize. Yet they complain about their jobs, they go to work every single day, every year for five to ten years. These people could easily just quit right now, never work a regular job again for almost a decade, and be totally fine. In those five to ten years they will almost certainly come up with some less restrictive way to make a bit of money. If not then whatever, you had a nice five year vacation, and if you’re really desperate you can go back to work again.

The idea that a million dollars isn’t insanely rich is a disease that causes people to stay at jobs, doing things they don’t enjoy, because they constantly need more and more money. The endless obsession with having more and more never ends. When I got my bank account to $10,000 for the first time, I was like “wow, I’m probably never going to have to work again”. It turns out I was right.