Poker- #20 in (Un)Common Writing Strategies- Why Every Freelance Writer Should Play Poker

by- Tom Kubrak


“But I don’t Gamble Tom.”

Well… you kind of do. You just may call it something else.

You’re a freelance writer for Christ’s sake! If that’s not gambling then I don’t know what is lol.

But…to-each-their-own I guess. Some call it gambling others call it looking for writing gigs.


If you want to be successful as a writer you have to be willing to go big. Write that story that no one else is touching and reach out to that place everyone else has been turned away from.

Sure you can play it small and write the story that everyone else is writing, but if you want to win big, you have to be willing to go all in from time to time.


Some writers are just naturally good at talking to those big publishing houses, agents and getting people’s attention. For whatever reason that may be. they’re good at it. Because of that, they don’t need any training.

But if you’re like me, a fairly new writer, I’m not good at this game. I find it hard to reach out to places/people I want to write for, and often get discouraged when people turn me down.

I not only play poker because I enjoy the competitive nature of the game, and the intense strategy it takes to win a game of poker, but I play it to “sharpen my mental sword.” I play it because I believe that this game of Freelance Writing demands preparation.

Playing poker is my way of preparing for what I’m going to face.


Like I said, I often find it difficult to reach out to people I want to write for; whether that’s a website, magazine, or someone I want to write a story about. The words(the right words) sometimes don’t come to me and I oftentimes say the wrong thing which turns prospective clients off.

So, poker is my secret way of developing a thick hide to withstand all of this.

Recently, as of this post, I’ve been on a hot streak with the group I play with, and have found myself winning or splitting the pot. But before that… I was losing- and losing a lot to say the least.


To put it nicely, I was betting on losing hands and I was trying to bluff my way to a victory in those games. I’m not the best bluffer. But in poker it should never be your go to strategy. I was doing it early on in these games I was losing too. I won a few hands in the beginning, which felt nice, but then came the hands that mattered-the BIG hands- and I kept the same strategy. The people I was playing with called my bets big time and I lost fast because I wouldn’t let go of my bluffing strategy.

This happened for many months and It took me a while to change this losing strategy.


Well, you can’t lie to these places and say you’re this amazing writer early on and ask for exorbitant amounts of money for your work. You sometimes have to be satisfied, in the beginning with, getting just a few dollars for your work(hopefully more, but you get the point). You have to know your worth early on and then work your way up.


I think poker helps with negotiating tactics too. When you have a good hand you’re going to bet more, but when you have a so-so hand that might win or might lose you’re going to stand your ground. So, with that being said, it’s about knowing when it’s your turn to bet high and lock in a deal that could change your writing career forever and knowing when it’s time to be satisfied with little wins.


Sometimes in writing you can go months without a gig. Worst case, YEARS. In that time it’s important to keep practicing your craft but the waiting game can be excruciating.

I recently played a game with someone who joined the game as a guest. Although this man was no guest to the game of poker, he was a guest to the game I run. His style of play, for the first few hours, was folding on almost every single hand. I was getting a little irritated because I had yet to play a hand to the end with this guy and wanted to go head to head with him. I never played with him so when I had him, finally, all in on a hand I actually left him 3 chips because I felt bad for him. BIG MISTAKE. That was enough for him to buy into the next hand and what happened next was the most miraculous come-back I have ever seen in poker. He came back and won the game outright.


What I learned from him was… be patient in the beginning, but when it’s your turn to bet big, and take over the game, do it. Don’t feel bad about it either.

He was taking out players left and right and just kept going. He found a winning strategy, after a bad start, and then ran with this new one until he ultimately won.


Yes…unfortunately if you’ve never played the game or have, and lost money, you may have already vowed to never play the game again. But I say..


…and go into the game with a plan and an amount of money that you are willing to lose(that won’t hurt you). That’s when poker can get uncomfortable for everyone at the table: when you know your friend is betting more than he should and is having a bad game.


In freelance writing you have to decide who your big clients are and who your smaller clients are. The bigger ones are the ones who are providing you with extra income to build your dreams bigger and the smaller ones being the ones that are allowing you to pay a few bills.

In another example: your big book idea might be your “big client” and your “small client” might be your article idea for that website.

Both are important but it’s important to separate these two because when it’s finally time to go ‘All in’ on one of these ideas you have to be ready.


Many beginner poker players don’t know how to cut it off. So if you do play… don’t be a fool. Cut yourself off when you realize it’s not your day and don’t bet any more of your hard earned money. Which brings me to my final point.


Poker is a game of skill not chance. Although many will argue this point, I do still believe that you’re going to win some and you’re going to lose some. And the games you lose are often from someone who is just a really good player. They’re rarely if ever, from someone who just randomly decided to play a game one day and came out on the winning side.

With that being said…before you jump into a game, or if you already are a poker player, tell yourself that you may lose. If that happens, don’t keep buying back into the game when you’ve hit your limit .

You lost…come back again with a different mindset and strategy. Don’t give in and quit the game because you had a bad day.


So…get in the game. Freelance writing is a game of skill not chance. The good writers will come out on top. The bad writers will leave because it’s too hard. But if you want to raise your chances of winning and locking in deals then you need a little bit of skill to do that.

In my opinion poker is the game for every freelance writer to play to raise their skill level. If you want to make some money then you need to understand and get educated on the business side. Poker is a way to do that. The creative side…well that’s for a different story.


Play the game and have some fun with it. If you don’t enjoy it and think of it purely as a way to make a couple extra bucks, poker probably isn’t the game for you. But if you know the benefits, in all aspects of playing this game, and you know how to have a good time with everyone who you’re playing with then poker is for you.

“I would advise anyone who aspires to a writing career that before developing his talent he would be wise to develop a thick hide.”

—Harper Lee, WD

Did you like this post? I’d love to hear your thoughts? Are you thinking about playing poker but are afraid? Why are you afraid? Maybe you play another game that helps you out…what’s that game? I’d love to try it out. Regardless, thank you for reading and send me an email or drop a comment. Cheers!


by- Tom Kubrak

Social- @tomkubrak

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