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.




29 thoughts on “I’m 38 Years Old and I’ve Never Had a Job

  1. Great article. I play chess daily and live poker twice a month (plus an occasional backgammon, bridge or table tennis tournament). I watch a lot of vlogs of pro poker players and their lifestyle. However you answered yourself.. 1M net worth is plenty for a single guy, but peanuts for a family in NYC area. Once you get your suburban 3BR house, 2 cars. a boat, pay for healthcare, retirement contributions and private education there is not much leftover to simply chill out. Plus index funds don’t always increase steadily by 4%. I lived through Nasdaq losing 80%.


    • One million is not peanuts for a family in NYC. You living in a bubble if you think that. There are literally tens of thousands upon thousand of people doing just fine with nowhere even close to that level of wealth.


    • That’s why living in NYC just isn’t worth it for the vast majority who have kids. I would add, however, that the boat and the private schools are easily skipped and play into exactly what this article is about….people voluntarily shackle themselves to jobs they hate with their own inflated expectations of what a good life is. Maybe the “good life” or even the “standard life” isn’t worth living. That’s what this article is about.


  2. Hi Greg,
    Great article and hook line!
    I have known you and your sister since you were young children. I am glad to see things going well for you. Parent support is a big key. I like to think I helped you guys a few times in Philly. I too dropped out of college and loved the pro chess life of doing most;y what you want, when you want. However, I followed the lead of Rohde (law school) and Sherzer (med school) after the “Russian invasion” and returned to school. Watching these guys “collude” was getting tougher to watch and they cut into the pay. I wound up with a Ph.D. in Pathology and Immunology and spent 14 years researching cancer and getting grants. I wanted a more stable job when I got married and chose teaching high school, and coaching basketball over college, where no one would let me coach. I had a few novelties published in the ECOs and informants and some in science https://www.ncbi.nlm.nih.gov/pubmed?term=mccarthy%20ba but I am glad I made the move

    I truly love getting up and going to school (and getting summers off). I also loved sleeping to 2 when playing chess. Sometimes “working for the man” can be rewarding and the health care does come in handy when needed. Your choices have served you well. I think the choices made by Rohde, Sherzer (also Wilder) have served them well. Kids are something else and you can’t realize it without one.

    That said, the 3 major contributions you have made to chess are laudable and are very positive contributions. I still teach online and my students, in person and online, have won 9 national titles so far. Getting a student into your camp means they will get some of the best training in the world!

    Keep it up!

    Dr. Brian McCarthy

    Liked by 1 person

  3. Greg is one of the few people who gets it. While everyone else is working for money, he is letting money work for him. Needless to say he is a chess master for a reason. Keep doing what you love.


  4. Yeah, after working a job and then getting fired or quitting, I would find “not working” to be very addictive!! I first “retired” at the age of 28, but my first retirement only lasted 8 years. So After working from age 36 to 40, I took another 4 years off. It was nice to take off 12 of 16 years so I could enjoy my life when I was still young.

    I also agree that people are obsessed with saving for their retirement. They really think 1 million dollars isn’t enough and are incredibly cheap with their money. They are afraid to enjoy life.

    By the way, I was also playing poker online and once had 15 consecutive months winning months, including the entire calendar year of 2007.

    Keep enjoying life!!


  5. Awesome story Greg! It took me longer to see the light but did finally quit my job for good last year at the age of 33. As a husband and father of two babies, I do have to be more careful than ten years ago, when I would work just long enough to go traveling. Still, freedom trumps the job!
    It is insane to me how risk averse most high earning American are. Even in the FIRE community, people are stressing about whether the 4% rule is secure enough, or will they need closer to 30-40x their annual spend before quitting the job they hate.


  6. I love the story! I play chess and a lot of poker is well in my 20s. But I was never quite good enough to make a livable income stream so focused on work instead.

    Are there people saying $1 million is not enough to live a happy life at your age? If so, that’s silly. But perhaps $1 million at 60 years old is a different story. Still good enough, but perhaps expectations are different after a lifetime of working.



  7. Great article Greg. As another chess aficionado (who won college championships but not anywhere near your level though), I am happy to see you made a great living out of Chess. Yeah, $1 million is easily enough if you live within 3-4% of that amount each year. Keep up the great work!


  8. Pingback: Best of the Personal Finance Blogs (8/4/17) - invibed

  9. Pingback: The 7 Personal Finance Articles We Loved This Week

  10. Greg, Sounds like you did have a job. You were simply able to turn your passion(chess) into money. Because it was your passion, It just didn’t seem like you were working. Congrats for that. That would be most people’s dream. It’s called being an entrepreneur. Also, grinding it out at poker is a job…a really hard job:)


  11. Smart asshole. XD I’m a dumb ass girl who cannot do anything but suck my thumb.. I’ve never had a job. Haven’t lived for quite that long either. Just starting out. But I could be comparable to the biggest failure of a person on this website. Hear me out. I’m not smart, My GPA was the lowest my Highschool has seen. I got put on probation in a junior college because I can’t do simple math equations like division. I envy you and the rest of the people who can afford to become jobless entrepreneurs. For those humans like me that have to struggle each and every day to do a simple task like remembering to brush my teeth or go to bed on time, or counting change, it really sucks. I’m not trying to put you down but really hear me out. Some People are born with handicaps and therefore cannot afford to live the lifestyle of someone who is smart because simply we are dumb as rocks. XD Or, I know I am at least. And Your story captivates me but it also makes me kind of hot with fury inside, cause you probably think many people could do this for themselves. When clearly we are all born differently. And no I could not be able to do this. As I struggle every damn day.. making my parents take care of me is a shame in my opinion. Probably best if I stop here though. There is a point to my comment I just wonder if you or anyone will actually be able or willing to read it? Because I’m sure this website hates these sorts of messages. Have a good rest of the day though. >__> also I wish I were smart enough to understand what Chess is. I’ve never played because people laugh at me when I ask dumb questions I guess.


    • Hi Jessica,

      Thanks for your message! I definitely don’t think that anyone could live the same type of life that I did. I also think there was a lot of luck involved. If I didn’t find chess, and just happen to be good at it, I have no idea how my life would have turned out.

      I tried to make it clear and acknowledge that everyone’s life circumstance is different in the beginning of the blog, but probably I didn’t do a good enough job. Here is the paragraph I am referring to:

      “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.”

      Also I certainly don’t think that someone who writes with the clarity and passion that you have is, in your words, “dumb as a rock”!

      Liked by 1 person

  12. Really good read. I share a very similar mindset regarding work.

    I got into affiliate marketing around 2011. Quit my job in 2012 and I’ve been doing it full time ever since. My biggest fear is returning back to the work place. Don’t think I could do it again now that I’ve tasted true freedom. Just the thought of it literally depresses me to the core.


    • What exactly is affiliate marketing and how do I go about starting it? Do you recommend any specifics websites for it? And is there a specific thing you need to know very well and love very much before you get into affiliate marketing? One more question…will this occupation end up with me being well-off financially, especially if I do this for the rest of my life?

      I will appreciate all the helpful advice you can give me. I really want the similar taste of freedom from the workplace you speak of here, because I’m in my late 20’s, currently unemployed from having to leave from a toxic workplace under a month ago, and I do NOT want to deal with some inconsiderate and heartless asshole boss during a 9 to 5 almost everyday weekly schedule EVER again…


  13. I can relate to your situation. I have a small trust fund thanks to the generosity of my grandparents. I am by no means wealthy, though. I have a middle class income from the trust and nothing more. Although I’ve held PT jobs briefly here and there, I have not work for most of my adult life… I must admit that I have felt quite marginalized at different times in my life… Don’t you just love those ‘what do you do for a living questions’… It is hard for people to understand our circumstances… People assume we are filthy rich ‘trust fund babies’ when they learn of our circumstances, and it just isn’t true. I’ve had my fair share of hard knocks in life too… I earned a teaching credential that I never put to good use. I do volunteer work off and on and take classes at the local community college ‘for fun’. Most people would envy my life, but I actually envy people who had to make it on their own merits… Well, knowing that there are others out there in similar circumstances helps.


  14. I can’t believe I came across another person who is around my age (I am 37 years old) and who has not really experienced the working lifestyle. I truly give you a lot of credit for being so daring as to follow what you were passionate about and not falling into the norms of society. I fear I am not as impervious to what we as Americans “should” be doing to give back. I feel guilty everyday when I hear of the new jobs statistics stating that the U.S. has more openings for jobs than it has applicants. After graduating college, I served in the military a measly 2.5 years until I was medically retired. I have not been able to turn my life into the promise that I held in my mind as a child; now, I feel completely hopeless and that I am just a leach on society. You are honestly the first person I have come across as to not be ashamed of saying, “Yes, I do not work.” However, I do feel you also have a “work ethic,” otherwise you would not have been able to get as far as you have in life. It’s rather an ingenious way of choosing to forge one’s own path, and all the credit to you. I found that failing to meet the natural stepping stones in life has severely damaged me mentally and psychically. I just don’t feel I have any purpose or passion anymore. In our country, everything revolves around “what you do,” and as I am sure you know, that is one of the first questions people ask whether it be at an informal social gathering or during a dental appointment. For me, it is utter shame and embarrassment. For you, I would brag too because you out-smarted the system. I wish I could have your positive outlook and maybe that is what it takes to be such a unique individual and step outside of mainstream society. I just don’t have whatever it is that you seem to innately possess–whether that be a penchant for chess or a man who wants to live each day the way he ever so desires. Good for you. Again, I am just surprised to see a title of a 38-year-old not working and damn proud of it. Continued success.


  15. Well good for you, Greg, you had well-off parents and weren’t going to end up on the streets. What about someone who comes from a background where both parents were bad with money, where just about everyone in their life has been bad with money, and who has never either been able to land a well-paid job (no family or other connections), or had the luxury of sponging off someone else?
    It’s been a lifelong issue, and not for want of trying. I am sick of it.
    If the possibility of going to jail didn’t bother me, I would rob all your assets and take all your trust fund money. The spirit of Robin Hood has never been so alive and well.


  16. For some reason, I googled “I have never had a real job” and landed here. I really relate to this article.

    I make jewelry as my “job”, basically whenever I feel like it.
    Sometimes I need a break, so I’ll spend months just going to festivals and spinning poi, but I always come back to making art. Then once I have jewelry, I just take a few nice photos and let it sell itself. My cost of living is also minimal, because someone who is only responsible for making art all day doesn’t need expensive crap.

    I have other projects in the works. Teaching more would be cool. More performance would be fun. I’m only 23 now, but I imagine that I’ll continue to build up a collection of revenue streams by following my heart. As it turns out, when you do what you love, the money part kinda just works out.

    Honestly, my only big problem with this lifestyle is relating to people who don’t live this way. It’s weird to me that other people have certain times they have to be places or that they can’t just get in my car when I offer to drive us across the country. Like… why don’t more people live like this? Are we really unique, or can this be taught?

    I’m interested to hear your thoughts.



  17. First of all some people here are right, you really did have a job if you were paid for teaching chess. Secondly this sounds to me like an excuse to not work, be lazy and escape the harsh realities of the REAL WORLD.


    • “Secondly this sounds to me like an excuse to not work, be lazy and escape the harsh realities of the REAL WORLD.”
      Sounds to me like a common ad homimen misconception I see people use to shame others for having a non-conventional way of thinking or a noncommital regard to the status quo of the “REAL WORLD” or “REALITY”, what ever that means. The real world is a vast landscape made of several different areas of realities, anecdotal experiences, ideals, concepts, etc….. So can you prove exactly how the author is just making an excuse to be lazy, as you so bluntly put it? Doing what you are passionate about, even if isn’t a traditional day job or working for money, isn’t the same thing as laziness. What’s funny is that in you’re first sentence, you even counter yourself be acknowledging the fact that he did work by having a job teaching chess, which is the total opposite of what you concluded.


      • If you are too busy defending someone else, please read the article again, I picked on the fact that the author contradicts himself by saying he never worked but he actually did. By the way, it’s your and not you’re as you’ve said in your closing statment. Have a good day I have no time to argue with fools who fail to understand English.


Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s