When we play games we are often doing that, just playing and trying to have fun. But games can easily become a competition, and much like athletic competitions, they can push us to improve our game. I can remember playing games with my parents when I was quite young. We would play Chess, Backgammon, Scrabble, Gin Rummy, Monopoly, Cribbage, etc. - the list was long. I still play Words With Friends (similar to Scrabble) with my mother almost every day. I do not need to win to have fun. But for me, if the other person is not trying, it is not as fun.
The first game I seriously studied was chess. My father had taught me from a young age and I was no longer a pushover by about 9 years old. I started checking out books on chess from the library and eventually bought my own copy of Modern Chess Openings, a must have for anyone serious about chess (though my copy is so old now there is nothing modern about it; I probably should get a newer edition). When I got to high school I could already beat anyone in the school chess club, so I became the first chair of our competitive team. I also joined the US Chess Federation (UCSF) which had a rating system which was used when you played in rated club matches or in tournaments. The ratings range from 1200 to 2500+. Everyone starts on the bottom, and even though I couldn't drive, I got in enough matches to move up rapidly. If you don't play people better than you, it is hard to improve rapidly. I got up to nearly 2000 (Candidate Master) before I simply ran out of time for competitive chess. I think I would have at least made 2200 (Master level) if I had kept it up, although you should know that International Grand Masters is a rating of 2500+ and requires a much higher level of dedication.
I have always thought about ways to make money playing games - some people call it gambling. I think of gambling as wagering money on an outcome you cannot control or reasonably predict. Slot machines? Clearly, gambling unless you have some illegal device for controlling the outcome. I don't get much of a thrill from gambling - I enjoy competing! Poker is a skill (the US court system has even figured that out). Blackjack is a skill which is why players who are good at it are not allowed to play per the casino management. When I first got a driver's license I got a weekly job dealing Texas Holdem poker for a rotating regular Friday night game. I dealt for tips until the game officially broke up at midnight when I would start to deal and play. It was a terrific way to learn the basics and observe good players.
When I got to Menlo College, I discovered there was a legal cardroom in Palo Alto (the Cameo Club) where you only needed to be 18 years old to play (I was only 17, but close enough). The game was no-limit 5-card poker. The beginning of each month I would triple the amount my parents sent me for my monthly spending money over just one or two evenings. It made college life much easier. When I transferred to Cornell I had to take a break from poker - there weren't any legal places to play and the Ivy League school was much too difficult for me to take that much time off from school and my on-campus job. When I returned to Calfornia I played in cardrooms. The game then was limit 5-card draw (A-to-5) lowball. I remember a crazy weekend where I went to play Friday night with only $30 to spend and turned it into $960 in about 4 hours. I actually took the entire $960 back to play again Sunday evening and ran it up to $1660. I called in sick the next day to go buy a rolltop desk and have a new car stereo system installed in my car. I reasoned I had not learned money management yet, so it was better to 'invest' the money in things I would keep instead of risking it by playing more. After that, I got married (to my lifetime partner, Anne) co-founded my first start-up company, raised a family and simply forgot about playing poker seriously.
Once I started my consulting business (2006), I once again found I could make time for poker (with my wife's support). I started reading books on poker voraciously, started playing online poker, and made occasional trips to northern California cardrooms. I was till pretty good and I was getting better quickly. The books also taught me about money management, variance, and other skills so that my poker would never interfere with our family finances. I also invested in an iPad app to track my play scientifically rather than just by how well I felt. In short, I worked hard to become a winning player. When Black Friday hit (online poker shut down in the US) I shifted to playing live poker. The only poker I play online now is a paid training site where I play against simulated players with lots of software tools to help me continue to improve. I will be happy to play online again if regulated online poker comes to the US market. Then in the summer of 2015, I felt I had truly turned a corner in my play. I decided to invest in a pair of prescription poker glasses. The first significant tournament I attended having trained extensively online and wearing my new glasses was a smashing success! I finished 3rd on a TV final table in the Heartland Poker Tour event at Thunder Valley. While third place came with a nice chunk of cash, I really enjoyed the validation of doing so well at a game I had invested so much time in.
I took a break from poker while working to change the landscape of recruiting in my efforts with Jerry Brown at Brown Venture Associates. I expect to be back at the poker tables competing again soon. This is a competitive game I can play for the rest of my life.