Nov 16 • The Human Side
Lessons From The Trail
"Winning"
Coming off my cabin retreat, I wrote a letter to myself about slowing down, staying aware, and taking life one step at a time. That clarity didn’t stay on the mountain. It followed me home. And one idea keeps looping in my mind:
I’ve spent much of my life trying to “win” at things that were never meant to be won.
I can’t “win” at fitness or wellness.
There’s no perfect number, no finish line.
If I push too hard or not enough, the system breaks.
I'll never complete all the challenges, run all the races, so enjoy the ones you do commit to.
Balance is what keeps me alive and in the game.
I can’t “win” a marriage.
If someone thinks they did, that’s… unfortunate.
And business? Leadership? Parenting?
Same thing.
There is no “done.”
There’s only whether I’m still playing — and how well, how consistently.
What game am I actually playing... And why?
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What the Trails Taught Me
Sure, there are destinations and markers and summits.
But the real objective is simple:
Take the next step. That’s it.
Extended hikes made this painfully obvious.
I noticed how fast things can slip when my mind goes anywhere else —looking out over the cliff, thinking about how far I’ve gone,
thinking about how far is left,
or getting distracted by wet leaves or loose stones.
It only takes a microsecond of not being present to stumble.
Trail hard?
Trail easy?
Doesn’t matter.
The focus doesn’t change:
one step — keep moving forward.
When the view is great, take a breath and enjoy it.
But then it’s time for the next step.
That's the only objective.
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Staying in the Game
I also had to listen to my body.
Eat before I’m starving.
Drink before I’m depleted.
Have a plan so I don’t crash.
Because if the tank goes empty, the steps stop.
And physical exhaustion drags the mind with it
just as fast as mental exhaustion drags the body.
If I slip, the only question is:
Will I get back up?
Can I get back up?
And when pain shows up — because it always does — ask:
Is this temporary?
Is pushing through worth the cost?
What growth is on the other side of this?
What pain am I avoiding?
I keep coming back to one line:
Pain is the price of freedom.
Not to be dramatic — in a real way.
Because sometimes pain comes from letting go of a dream, idea, or opportunity...
If I want to stay in the game, I have to accept the toll.
So this is where I’m at
I’m not trying to win anymore.
I’m trying to stay balanced — and stay "alive" in the game I actually care about.
Because being ALIVE is a FEELING.
Pain is a good reminder to not just be one among the living.
One step at a time.
One moment at a time.
Adelante.
If you’re here reading this, I’ll leave you with the same question I’m sitting with:
What game are you playing? And why?
What does winning look like to you?
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Lessons From The Trail
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