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.
So, what are my options now? I suppose I could "get a job," but what? Like many of my peers in online poker, I have no college degree, no immediately marketable skills, and a gaping six-year hole in my résumé. While no one is entitled to make a living from his home office—or even doing something that he enjoys—the prospect of entering another field is daunting, if not impossible, for a lot of people in my position.
A more practical path might be to try to earn a living playing live poker. There are a couple of ways to do this. One is to play in local "cash games." The other is to travel around the world to play in high-stakes poker tournaments. While both are theoretically viable, there are major drawbacks and obstacles here. Playing live games necessitates living close to a casino. As for tournaments, you need a very large bankroll to sidestep potential ruin in the face of large buy-ins and travel expenses. Neither option is feasible for large factions of the poker-playing world, particularly those who supported families with the income they earned playing poker at home.
Going into 2011, I decided to play as little live poker as possible. I regarded my previous year in poker as a failure largely due to my inability to balance a live schedule with a steady regimen of online poker. My ambitions to travel the world and play the live circuit caused me to get out of the good zone I'd been in playing poker from a computer in California, and it destroyed the upswing I was on during the first quarter of the year. The opportunity cost that comes along with playing live poker tournaments is very high. Large financial downswings are more likely to happen in live poker, and the time spent traveling to tournaments is time removed from the more stable online poker grind.
One of the essential advantages of online poker is the ability to have a steady positive expectation on a relatively small bankroll. For example, a player who plays 20 tournaments online each day, each with an average buy-in of $100 and a 20 percent average return on investment, can expect to make $400 a day in the long run. That same 20 percent ROI would translate to a $2,000 expected return in the sort of $10,000 buy-in event that is commonly televised on ESPN. The difference is that the time spent to achieve those earnings in a live event will be days as opposed to hours. More significantly, the chance of going on a 20-tournament downswing is equally likely but far more costly live—a loss of $200,000 as compared with $2,000.
The pitfalls of live poker leave me pondering a third option, one that's the most drastic but also possibly the most desirable: Move to another country. If I left the United States, I could keep working from home and continue to earn money playing poker online. Leaving aside the logistical and emotional hurdles related to going abroad, I need to decide which of the last two choices I prefer. I can stay in the city I love but spend most of my time in casinos and card rooms, environments I don't particularly like. Or, I can pick up my home-office setup and relocate for some period to a foreign country, maintaining the same structure and lifestyle I have now.
While the world of professional poker is viewed by outsiders with an air of mystery and skepticism, it was very real and straightforward for those of us who got started during the online poker boom. We approached the game studiously and built relationships with our fellow players and with the sites we relied on in order to deposit and withdraw funds. We paid our bills and our taxes and built lives with the money we earned. All of this might seem illusory to an outsider, but it was never a fantasy to me. Now, like thousands of my fellow pros, I'm trapped in a strange void—unsure when, if ever, online poker will be legalized in this country, and at a loss about what I should do next.