Come tax time, you’ll need to collect, organize, and report your various income and tax forms to the IRS and state government. But long before the filing forms start arriving in your mailbox, you need to keep reliable documentation of different aspects of your gambling and poker activities. For the time being, I’m going to side step the various ethical and legal issues that come with reporting various types of poker winnings. (If you’re interested, you can read more about these issues here.) Instead, I want to focus on the biggest and most common mistake you can make: Failing to document your poker losses and legitimate business expenses.   

Here’s the deal: When you’re in a Las Vegas casino or some other institutional poker setting, that institution is going to document and report any winnings of a certain size. What they’re not going to report is any losses and expenses you also incur. Crucially, these losses and expenses can be used to offset your gross winnings and taxable income. If you play in casinos, these expenses include basic travel expenses. If you play online, these expenses include your computer, internet charges, and other telecommunication costs. You can even deduct the cost of any poker books and training materials that you purchase.  

Depending on your circumstances, tax filings can get incredibly complicated. Poker tax accountants cater to this crowd. Don’t let an institution give you excuses about providing these filing forms. Nowadays, comprehensive accounting software must include support for Form W-2G. You have every reason to expect to receive this form in a timely manner.  

Hi, my name is Drew, and I was a poker grinder in the truest sense of the word. I played poker for a living for the better part of five years during and just after grad school. I made enough to live on, but not especially comfortably, and while I did have a decent chunk of change when I left, it was far from life-changing money.   

I was never that next-level genius, but I had enough math skills to do any number of things. The hitch was that I liked people too much to dwell in such an abstract world. Or at least I was too interested in people to relegate myself to the world of numbers. Yes, I get that math is everywhere in the real world and the poker table even more so than many places. This was always part of the appeal, but the restless nights I spent after a particularly frustrating session were often more about the style of play and the personalities involved. I wouldn’t say I took these moments personally, but it was the human element that was the puzzle I would keep turning over and over like a Rubik’s Cube. 

In fact, in many ways, poker had started to feel like this kind of pure math, and this was a big factor in why I decided to leave. For a long time, the grind was about the external goals of making a living, building up my funds, and working toward that day when it wasn’t such a grind. But then, the grind itself became a grind. I don’t know if poker was ever truly going to be one of the great loves of my life, but it was becoming something I actively despised or dreaded. A couple times near the end, I left the table a lot earlier than I planned just because it was getting so hard to maintain sufficient concentration.  

In retrospect, I think I left just in time. After a couple years away from the poker table altogether, I was invited to a couple home games with friendly stakes. It was a different experience altogether and not just because I wasn’t grinding anymore. It was just such a natural and effortless way to get to know people. It was poker as a means to an end, not an end unto itself. This led me to start thinking about how poker has so much to offer both the amateur and professional player in terms of insight about life in general. This site explores how you can use poker odds and the rules of engagement to make a better living, but also to just live better.  

Many successful poker pros spent months, or more often years, being a grinder. The term can mean a few different things. In one sense, it refers to the mental grind and general stress of earning a living by playing poker. Indeed, it’s tough enough to consistently make the best decisions possible at the poker table without also having to think about whether the river is going to make it a dicey proposition to pay rent and still have stake money. There’s a reason that poker chips are frequently talked about as ammunition. It’s odd because the poker chips actually do represent real money, but I agree that it can be poisonous to the poker player and the decision-making process to see chips as your food and housing costs.  

Keep track of each hand. A lot of professional poker players and serious amateurs take notes at the poker table. This is a great practice that can help refine and continuously improve your granular decisions, both during the session and afterward. The simple ability to accurately remember exactly how a hand played out is itself an important resource. Somewhat surprisingly, it also helped me not to dwell for too long on any hands that got to me a little more than it should have.  

I’ve also found the act of note-taking helps create a table image that accentuates other players’ tendencies. In other words, in my experience, taking notes at the poker table made tighter players play even tighter and looser players even more aggressive. But I would also have a corner of the page reserved for doodling so that I could pretend to be making notes when I really wasn’t. 

Keep track of every session, too. Being a grinder can also refer to a poker player who tries to pick their spots in such a way that they have a consistent advantage and can reliably walk away ahead even if the winnings aren’t that big. What I learned after being a grinder for a while is that you should also track certain data points for every one of your sessions. Some of the information I kept track of were: Game (style), Stakes, Take, Total Hours, Take/Hour, Site and Play. Play was a subjective ranking of whether I thought the table was normal, tight, or loose.  

Most people talk about picking their spots in that they feel they consistently held an advantage over the table. Okay, but this isn’t the whole story. I had one fellow grinder friend start using this spreadsheet approach, and he discovered that not only was he was making more money per hour playing at a higher-stakes table, he was more consistently ahead when playing slightly higher-level competition. For a while, I also tracked my performance hour-over-hour to see if I had better results at the beginning, middle, or end of a session. I didn’t get a lot of insights, which surprised me. I figured, either my read on the table would improve or mental fatigue might set in or something else. 

Anyway, it’s this two-pronged approach to picking your spots that I found most effective for maximizing my time at the poker table overall. Interestingly, of the two approaches, I think keeping track of each session was more important. But maybe this is because replaying individual hands also comes more naturally to the typical poker player.  

Whether it’s pocket aces or flopping the nuts, one of the skills that’s important to develop as a poker player is what to do when you have a monster hand. The primary calculation here is how to extract the most chips. (Depending on the situation, you also need to be mindful of getting blind-sided. Just how stone-cold are your nuts? If the worst-hand in poker is the second-best hand, it’s especially cruel when the second-best hand used to be the best hand possible.)   

That said, there’s still a ton of nuance involved just by focusing on extracting the most chips possible. The check-raise seems most natural, but projecting this much strength will also end up scaring off a lot of would-be bettors. Many pros will bet-out in the hopes of disguising their true strength, while also growing the size of the pot. If the opponent folds, you can legitimately question how many chips they were ever going to put in the pot anyway. The check-call also has the advantage of ensuring you keep the opponent on the hook for at least another betting round. Your opponent may perceive weakness on your part and potentially increase the strength of their own hand inducing them to bet on subsequent betting rounds.  

The board also plays a role in the relative wisdom of each type of decision. If you’re holding a pair and you flop the top set, for example, it’s essential that you look at the rest of the board. If there are straight and flush draws already on the board, I’m more likely to bet-out. If there are limited or no flush and straight draws on the board, I’m more likely to check and see if my opponent will make a bet. Even still, the advantage of any particular strategy is muted by becoming too predictable in your play overall.  

So, how does this principle apply to other areas of life? Well, let’s say you’re dealing with office politics and that always touchy subject of taking and getting credit for your work. You want to make sure you get your due credit, while also seeming like a team player, right? This is why I like to consider the relative ease or difficulty in someone taking credit for my work. Simply put, if I know it would be extremely hard or risky for someone to take credit for my work, I’m more likely to get my head down and wait for someone to notice with the intent of getting extra points for my discretion. Conversely, I’ll be more on the lookout for opportunities to mention my work when I think there’s a danger of someone butting in.  

No doubt, there are dozens of different ways I could talk about the intersection between poker and luck. But one of the things that’s always resonated for me, and continues to resonate, is how often bad luck first appears to be good luck, and vice versa:  

“When the gods wish to punish us, they answer our prayers.”

“The worst hand in poker is always the second-best hand.”

“You’re never as high or as low as you think.”

You hit the flush on the river only to have your opponent hit a full house at the same time. You can say that you should be able to make a great laydown, but come on. Sometimes, it is pure luck, and it’s a roller coaster ride. You get all your money in with a pair of Ks, only to go up against As. You spike yours on the flop, they spike theirs on the turn, and it all ends up as a split pot with Broadway coming on the river.  

So, it is in life. Part of you has to be ready to accept the good fortune and endure the bad fortune, but another part of you has to be ready to question whether the good luck is really good and whether the bad luck is really bad. Sliding Doors is an underrated movie, by the way.