High Stakes Writing
What three years of semi-professional poker taught me about mastering a craft.
February 6th, 2025: I have one more week in Da Nang, Vietnam, before heading to Chiang Mai, Thailand. It’s been an amazing month here. I’ll miss my long walks along the beach, the consistent 70-degrees and sun, and the vegan restaurant I get lunch at almost every day.
It started as an attempt to fill a Saturday afternoon. It ended when I won a tournament in St. Louis for $46,000. It lasted three years. 200,000 hands. 2,500 hours of play. By the end, I was a semi-professional. According to Google, that means I was receiving payment for it but not relying entirely on it for a living. I was receiving payments…usually. Sometimes I was the one paying.
I’ve spent four years studying math, two getting an MBA, and four at a top consulting firm. I’ve read enough books to fill a warehouse. Listened to enough podcasts to wear through the cords of all my earbuds. And yet it’s this. A game that would invade ESPN while I was watching real sports. A game I laughed at my high school friends for playing. A game I thought was for low-lives and gamblers.
It’s poker. And it’s the best map – the only map – I have for mastering anything.
When I was too absorbed to remember the day of the week, too addicted to go a night without dreaming of pocket Aces, I didn’t realize how much poker was teaching me about mastery. But as writing has shifted from a side interest to the craft I’m trying to master, I’ve started to look to the years I spent pushing chips across a felt table for inspiration and guidance. Writing and poker feel…eerily similar. The depth of the crafts. The around-the-clock rumination. The battle for every inch of improvement. The inability to explain why I keep showing up.
We’re never taught how to master a craft in school. Or master anything, really. Maybe that’s because it can’t be taught in school. Maybe it can only be taught by getting dizzyingly lost in something for no reason. Just for the love of it. Because every moment not doing it feels wasted. Because the highs feel like being pumped full of ecstasy and helium. Because the lows feel so soul-destroying there's only one option: to keep going. To keep learning. To keep trying to get better.
Poker was the best education in mastery I ever got. These nine lessons cycle on repeat in my head as I walk a similar path of mastery in writing ten years later.
You’ll discover infinite complexity in a seemingly simple craft.
Poker is a game of chips and cards. That’s it. Nothing more, nothing less. Yet, it is more. Somehow.
When you started playing, you watched a video featuring the two best players in the world. One player made a giant bet and his opponent considered calling – matching the bet – for ten minutes. Neither player had anything…two bad hands playing a massive pot. Each seemed to be reading the other’s mind, knew the other had a weak hand based on – from what you could see – nothing. It felt like magic.
You knew there were levels you were blind to. So you set out to see them. You couldn’t tolerate not seeing them. And as you uncovered levels, you realized there were only more levels, like opening one Russian Nesting Doll after another.
You’ll look like a fool…and that’s a good thing.
In your first dozen dorm-room games, you lit $20 on fire like it was an offering to the gods. In your first casino game, you tossed $200 into the furnace before you got comfortable in your chair. You dumped hundreds playing online. You put your results in a spreadsheet and wondered how much further you could dip into the red before you’d have to stop playing.
One day, around six months in, you moved from the red to the black. It came out of nowhere. No lightning-bolt moment. No big flip of a switch. Just enough hours looking like a fool. Soon two guys you played with, who played poker all through high school, were asking you whether you’d bluff on the river with a missed flush draw. Soon you understood how the pros knew their opponents were weak…because giant bets typically meant players either had very strong or very weak hands.
The only reason you won money was because you were willing to look stupid and naive, putting your ass and your cash on the line before you had a clue what you were doing. In retrospect, this doesn’t look stupid or naive. It looks genius.
Your obsession doesn't need to make sense to anyone…even you.
You’d finish your homework at 9PM and almost trip over yourself as you sped-walked – sometimes in finger-freezing cold or waist-high snow – to a dorm on the opposite side of campus. By then you’d been fantasizing all day about full houses, making perfect reads on your opponents, building chip stacks so big they’d fall over. Now, so close to gametime, you wanted to take off and run. But you didn't want to be seen sprinting across campus.
The group of five to ten would convene at a makeshift table in a lion’s den hideout…at last. Yet, you still felt odd about what you were up to: Why am I so drawn to this? Is this really what I’m doing in college?
Your fraternity brothers looked at you with cocked heads and wide eyes, wondering why you were playing cards until 4AM instead of partying with sorority girls. You phrased your nightly escapades to your parents as a social thing: “I hang out with a few guys and we play some poker. But mostly hang out.”
The desire to play outweighed all the doubts…including your own.
You’ll ride big waves in the short-term, but only the long-term counts.
The walls of your brain are graffitied with moments the outcome didn’t reward your effort. When you outplayed an opponent at 2AM, only for him to hit a lucky card to win a $2,000 pot. When you flew to Florida for a tournament and paid $500 to enter, only for another opponent to get lucky and send you home after 50 minutes.
The walls of your brain are also tattooed with moments when things did go according to plan…or better. Like when you flew to the Bahamas and played a qualifying tournament hoping for entry into the $5,000 Main Event. The qualifier lasted ten hours. It ended at 2AM. You got in. You screamed when you got back to your hotel room and woke your friends. The next day, you clicked open the table assignment PDF and almost dropped your phone. You’d be sitting across from a guy you watched win $15M in the biggest poker tournament ever the year before.
You never controlled all the variables. Especially in the short-term. Sometimes things went to shit, other times they soared. But in the long-term, your effort was rewarded. You won over $70K as a student. You knew even when the individual sessions sucked, or when it felt like you could walk on water, the overarching progress was more important.
You’ll improve quickly if you dedicate yourself.
Three months in, you told a friend: “I just want to play at the casino and not lose everything.”
Two and a half years later, you won a $46,000 tournament. You could walk up to almost any game and feel like a favorite. When you faced Chris Moneymaker and Ryan Reiss – two World Series of Poker Main Event champions – you didn’t feel out of place.
This exponential growth came from a burning obsession and diligent practice. One of the dealers at a casino in St. Louis nicknamed you The Grinder because you were there so much. You didn’t take many days off. You didn’t take many moments off. But you loved it, and that drove you to put in the work.
You’ll thrive with a style that fits you. And excites you.
You were conservative, but brave. In poker, it’s called tight-aggressive. You picked your spots to go for the pot. You could have played differently, but this felt natural. Like an expression of you. You’re not impulsive and reckless. You're calculated. Intentional.
You’ll feel like a psycho.
Your obsessiveness will sometimes feel psychotic. Like the time you left the casino with your two friends at 10PM to go see a movie, saw the movie…then went back to the casino. Or when you stayed at a Florida casino until 4AM…and had a flight to catch at 7. Or when you stayed at an Indian reservation casino in upstate New York and one of your friends played for 36 hours…and you weren’t far behind.
You will feel addicted. You will occasionally wish you didn’t care so much. You will feel like you’re getting sucked into a black hole.
You’ll look back in a week, or a year, or a decade, and find wisdom.
Who would have thought a random campus poker tournament would lead to you writing an essay ten years later? And that it would be serving as a map for later pursuits of mastery?
Dedicating yourself – when the outcomes weren’t clear, the payoff wasn’t certain, and the journey would be long – was an act of faith. Faith that the joy of the present was enough, even if nothing came of it. Faith that with sustained effort, a path would unfold.
Following your faith didn’t just lead to money that funded a post-grad Euro trip and some S&P 500 shares, but wisdom. Yeah. Wisdom. Sitting in smokey casinos and desolate dorm basements turned into wisdom.
You’ll love the craft. But you’ll love the friends you make more.
Ten years since your first hand, you don’t play anymore. But what do you have? Six friends you still take an annual vacation with. Who you’ve been groomsmen for. Who may one day stand as your groomsmen.
Memories of poker hands line your head, but memories of your friends line your heart. Waking other students with your midnight laughs and screams. Eating chicken in the dining hall at 3AM when the game finally ended. Analyzing hands until dawn. Driving across state borders to Indian reservation casinos. Flying to Florida, the Bahamas, and Las Vegas.
You mastered the craft in community. Not by yourself. By hearing others’ perspectives. Disagreeing. Challenging each other. This taught you more than any book. And it meant more, too.
You’ll have trouble getting up from the table.
You’ll work overtime. Just because. Like now – writing a tenth lesson when you said there’d be nine.
I spent ten hours writing this essay. Fifteen if I include the original draft I threw out. At least thirty if I include daydreaming at the beach and brainstorming ideas at all hours. Three times I wanted to throw my laptop into the ocean. A few times I wanted to close it, look up at the blue sky, smile, and celebrate reaching into the unknown and capturing an idea worth sharing.
That just about sums up the path of mastery. The highest highs, the lowest lows. The feelings of brilliance and insanity…simultaneously. The hours toiling, sometimes making progress, sometimes going backwards, many times standing still. The messiness, the not knowing how it will turn out.
Even with these lessons, it feels like I’m plunging head first into the deep blue sea. This time, though, I know – it’s exactly how it’s supposed to feel.
The Grinder is back,
Thank you to
for your edits on the initial draft of this piece.👋 More travel updates:
A mentor suggested I go to Luang Prabang in Laos. If anyone’s been there I’d love to hear your experience. I envisioned myself spending ~1-2 months in Chiang Mai but I heard they start burning rice fields in March and the air quality gets awful.
Life in Da Nang has been simple — writing, beach, walking, hanging out with the other artists. Maybe they’re saying the same about me: “We hang out with this other artist named Jeremy.” It’s an interesting identity for me to try on.
Thanks for reading!
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Such a good analogy and a great way of thinking about the craft of writing!
I love knowing about this era of your life, the obsession, the growth. And so natural. I wonder how much of us seek to create that for ourselves when the real answer is to wait patiently until it finds you - much as poker did for you.