The Athletic Philosopher

The Athletic Philosopher

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The Athletic Philosopher
The Athletic Philosopher
Stop playing the wrong way

Stop playing the wrong way

Start having fun like this instead

Jordan B. Goldstein's avatar
Jordan B. Goldstein
Jul 17, 2025
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The Athletic Philosopher
The Athletic Philosopher
Stop playing the wrong way
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Getting Fun Right

“Desperate, twisting, thrilling fun that hurts so much you want it to stop, and need it to go on” Ken Dryden, The Game

This quote stood out to me in bright red this morning as I read more pages in the greatest sports book written by an athlete. Fun is always at the top of my mind, especially when it comes to sports.

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I believe that fun is an important spiritual signal that indicates a pathway to self-discovery, self-knowledge, self improvement, and ultimately to self-mastery.

But it’s not the type of fun we see promoted to us, especially as adults.

What most call fun is simply ‘pleasure’ and is too often related to consuming, it’s never related to experiencing and learning.

That’s why this Dryden quote hits HARD.

It’s like the fun of a rollercoaster, strapped in, nowhere to go, on a ride, you riding too, anticipating the thrill, but always caught off guard, not quite able to get ahold of it, but never willing to stop trying.

This is the fun you’re missing when you say things like

  • “I don’t feel at all like myself”

  • “There’s not much enthusiasm in my life today”

  • “I know what I need to do, but I still don’t do it”

  • “It feels like I just drift too often”

Just like Dryden intimated in his brilliant description of the excitement that comes over you when the game picks up, opens up, into it’s greatest dramatic potential, it’s this type of challenging, daring, exploratory type of fun that produces meaning, interest, and most importantly INTENTION.

Harnessing Fun

This week I’ve been writing about my reintroduction to 3 sport training in advance of competing in two big triathlon races next year.

It’s a great illustration of the dynamic push and pull of this ‘intense’ kind of fun. I desire the challenge for numerous reasons, a bit scary, but too compelling to give up.

But what I want to highlight for you today is how this type of exhilarating fun creates incredible INTENTION in your attitude and actions.

Think of it this way, when I run on a running path without cars I can literally zone right out of the experience. My body move mechanically, automatically, and my intention often dips. It’s why I find it hard to really test my speed outside, I just am not engaged enough to keep my focus high.

A treadmill however can do it. Because if I set it at the speed I want to run, if I make one wrong step, I will fly off the back and injure myself badly. But what a FUN challenge it is to try and beat the machine and crush a time PR. I’m much more INTENTIONAL about it.

So my advice today is clear. If you’re struggling to gain traction, find consistency, show up for yourself, you need a proper dosage of FUN to help bring back your attention, focus, and intention.

Make sure it’s got a bit of daring, a bit of uncertainty, a bit of fear.

You’ll be awoken out of your slumber and jolted into action.

But it won’t be from a bully threatening to punish you, it will instead by like a nurturing parent pushing you into the swimming pool when you aren’t sure you can swim, but the parent knows you need to just go if you’re to learn properly.

Below the paywall I’m going to share an important prompt to help you understand this type of fun more personally, so that you can ACT and incorporate this type of fun into your life.

It’s a way to use fitness and exercise as the first step.

I’m also going to provide direct comments and help you make sense of the fun impulse inside you and aim you towards real actions and strategies you can take.

But here’s something to chew on if you’re not yet a paid subscriber.

“What do I mean when I say something is ‘fun’ to me and is it really what I desire or what other’s tell me I should think is ‘fun’?”

Then think about the quote at the beginning of this article and see if there’s a match, or mismatch. My messages are always open so please if you have questions or want some direct advice, hit me up with a message or drop a line in the comments!

I wish you all more fun, the right kind of course!

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