For most of the last six years, my daily routine consisted of waking up in the morning and playing online poker tournaments. Like most self-employed people, I had some flexibility in my schedule, but paying the bills was ultimately a function of putting in hours. My workday began when I turned on my computer at around 8:30 a.m. Typically, I would play more than 20 tournaments in a day, usually four or more at the same time, and I'd clock out when I busted out of—or, on a good day, won—the last of my events. On a Sunday, the busiest workday for an online tournament pro, I'd play as many as 40 tournaments, stretched out over 13-plus hours.
That all changed abruptly on April 15, a day that's been termed "Black Friday" in the poker world. That morning, the Department of Justice unsealed an indictment against the three biggest poker sites. PokerStars, the site where I played daily—and the site that sponsors me—responded by cutting off Americans' access to real-money games. The effect on my livelihood was instantaneous and total: I woke up to find that my career was in jeopardy, and that my options going forward were ambiguous.
Professional poker players existed before cyberspace, but today's young professionals arose mostly thanks to the Internet. The ability to play hands at a significantly faster rate than at a "live" poker table created an enormous experiential benefit. Success that might have previously taken decades to achieve was suddenly attainable in months.
In 2005, the year I left my job waiting tables to play poker full time, an entire society formed around online poker. People from all over the world competed for real money every day, and it became commonplace to encounter people, many in their late teens and early 20s, who were making a living playing poker. Scores of otherwise aimless college dropouts were in the process of accumulating six- and seven-figure bankrolls and refining the necessary skill set—a combination of discipline and objective analysis pitched against an inherent component of risk—to maintain their success. Since then, online poker has only gotten bigger. These days, it seems everyone I meet knows someone who plays poker for a living.
All of that just adds to the feeling of collective doom I am experiencing. Many of my closest and most trusted friendships were formed in the poker world. There's a unique bond among people who compete against each other for tens of thousands of dollars (or more), looking for edges wherever available, but leave the cutthroat nature of the game behind when it's time for dinner. We are aware of the luxuries afforded by our profession—the ability to travel around the world playing a card game, the ability to take a day off when we're burnt out or our game is "off." We're also aware of the existential crises associated with our work—the isolation created by days spent in front of a computer screen, the emotional and financial swings, the looming question about whether or not we are "contributing to society."
While I am still pretty shocked and depressed, I have to rely on the same sort of objective analysis I learned as a poker player to make the best decision about my future. Similar to a difficult poker hand, I am forced to choose between the best of a few undesirable options. I have to make adjustments to my career path and lifestyle that will affect the course of my entire life, and I have to do it soon. The short-term solution will probably not be all that desirable, and the challenge is figuring out which of my options will create the highest level of long-term prosperity.
I come from an upper-middle-class background. I went to a good high school in New York, but I rebelled against going to college and was mostly directionless during my 20s. I had a flash of a career as a writer, but I lacked the motivation and direction to realize my potential. I worked as a bike messenger, a customer service rep, a busboy, and a waiter before poker came along. Although I enjoyed plenty of privilege in this world, I found a true career only when I became a professional gambler in my late 20s.