Creative Wayfinding For Ambitious Optimists.

The Creative Poker Game

August, 20, 2022

Pursuing creative work is a bit like buying into a game of poker.

We can refrain from betting on every single hand we’re dealt and still have our chips slowly eaten away at as hand after hand we pay the minimum ante to simply stay in the game.

We can spend the whole game playing it safe, waiting for the perfect timing for our perfect hand only to have the opportunity fail to materialize.

Or, maybe it does materialize…

When it does, our eyes light up, we go all in, play the hand perfectly… and yet against all odds another player might happen to have something even better.

We leave the game dejected, with the knowledge that even our best wasn’t good enough to win.

Great creators, like great poker players, understand that sometimes you have to bluff your way through when it feels like you don’t have much to work with.

And sure, sometimes you get caught and are forced to admit that you were in over your head and it’s time to go back to the drawing board.

But sometimes you get away with it, and are emboldened to move forward with more confidence.

Great players know how to read the table, to sense opportunity, and move to take what they can get. To see confidence and distinguish strength from bravado. To swim in the currents of emotion and timing and chance and opportunity.

They know that the game is about so much more than simply the cards you’re dealt.

They know that it’s hard to win without ever taking a risk or pushing your luck.

And that even when your luck eventually runs out (and it will), it’s not the end of the world.

You can always buy in again after all.

And unlike poker, the cost of buying back in to your next creative endeavour is measured not in money but in curiosity, hope, and an idea worth exploring.


Explore how to navigate a creative life that matters

This article originally appeared in my weekly Creative Wayfinding Newsletter. Each issue is the product of a week of work, and contains something not available for sale.

A fresh perspective, a shot of encouragement when you need it most, and maybe even some genuine wisdom from time to time.

Each week, we explore a different facet of the question “How do we navigate the wilds of creating work that matters?”

It’s something I’m proud to create and I’d be honoured to share it with you.


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    Hi, I'm Jeremy, I'm glad you're here.

    No matter what you create, I'm guessing you spend a good amount of time feeling lost, hopeless, and unsure about how to get from where you are to where you want to be.

    So do I. And so does everyone doing creative work.

    This is the Creative Wilderness.

    Every week, I publish a new article in my Creative Wayfinding newsletter about how we as creators and marketers can navigate it with more clarity and confidence.

    If you're building something that matters, but aren't quite sure how to take the next step forward, I'd be honoured to have you join us.