Doing 1-1 sessions with Cash Cabins.
Speaking regularly and doing podcasts.
Writing blogs.
Launching my licensing program for insurance advisors.
Raising two boys.
Healing my kidneys and radically changing my food (with excellent results).
Adding people to the team to better serve and create capacity.
Carving out time to connect with people on social media directly through texts and calls.
Oh, and I’m still doing some comedy.
Play for the sake of play.
We share stories.
We share laughs.
We share life.
And my dad and sister are so easy to love.
It especially helps me to think, be present, and even lose track of time.
Not looking at what time it is.
There is nothing to do but slowly and quietly walk from point to point. Alert. Present.
What allows you to evaluate your life?
Where can you listen to yourself for an extended time?
The elk is resting under a tree at the top of the canyon.
John uses a cow call to get the bulls attention.
Another call.
He stands up—one more call.
The elk is now 600 yards and a mountain away but starts walking towards us.
I hid next to a tree.
As I prepare, I try to range the distance to other bushes and trees.
I calm my breathing and take out an arrow. I knock the arrow and wait.
It doesn’t take long.
The next thing I know, the bull is trotting up the hill.
I have no time to react.
I hold still.
My breath becomes shallow, I feel the adrenaline release.
My legs feel slightly shaky.
Faster than expected.
He stops and stares at me.
My dad was by my side, and the guide was a hundred yards away, trying to cover behind a small bush.
I see him through the side of my eye, trying to avoid eye contact.
He might be thirty-five yards away.
I hold still.
I wait.
Over a minute passes.
WHAT! How?
I’ve been shooting regularly and consider myself accurate.
Hindsight is more 20/20.
I didn’t know what was going to happen.
I’ve been in this situation when the elk ran off before I got to shoot.
This is part of why it is so exciting.
He missed multiple times during his first year in New Mexico.
I asked him if he felt better after seeing me.
Part of the process.
In hunting and in life.
One of the hardest workouts of my life.
Maybe the meat will taste even better.
I learned.
Hard things make you stronger.
David Goggins’s voice in my ear, “You can do 40 percent more than you think.” Finding Nemo’s Dory chanting, “Just keep swimming (hiking).”
What experiences raise the stakes and can teach you more about yourself (and life) while you have some fun along the way?
Garrett
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Frequently Asked Questions
Why is creating time to play important for entrepreneurs?
Play isn’t a luxury — it’s essential for creativity, perspective, and sustainable performance. Without space to think and let go, you burn out and lose the edge that made you successful in the first place.
How do busy entrepreneurs find time for fun?
You don’t find time — you create it by prioritizing it like any other business objective. If you can carve out time for meetings and podcasts, you can carve out time to play. It starts with permission and intentionality.
What is Win Then Play?
Win Then Play is the philosophy of building a life from which you don’t want to retire — winning by playing, not grinding now to play later. It means integrating enjoyment into the process, not deferring it until someday.
How does play impact business success?
Play creates space for insights, reduces stress, and keeps you connected to why you started. The best ideas don’t come from grinding harder — they come from stepping back, having fun, and letting your brain breathe.



3 thoughts on “Are You Creating Time to Play?”
Garrett – I read this blog post a while back and thoroughly related to the hunting story due to being a hunter in Alaska. Well I just returned from a deer hunt and had a very similar experience where we had a golden opportunity on a Sitka black tail deer ON THE SHORE yet I sadly missed my one opportunity. The excitement and surprise was quickly met with disappointment and anger at myself for missing. It has since replayed in my head over and over, producing feelings of grief and even self loathing. Hunting is unique in that way – months of build up, preparation, logistics that sometimes culminate into one opportunity to capitalize. The reward can be great but the miss can be devastating. I wanted to share this recent story as a way to connect and process my feelings that still sting now that I’m back home (without any deer meat). I appreciate you
Dylan. Yeah. So much in a moment. All truth. You get it or don’t.
Glad to see you are reading these. Hope all is well.
This article beautifully captures the essence of finding joy, connection, and self-discovery through play and purpose. Garrett’s storytelling inspires reflection on cherishing meaningful experiences with loved ones, embracing life’s lessons, and prioritizing what truly matters. A heartfelt reminder to create space for both growth and gratitude in our busy lives.