Essay: The Poetry of the Long Game

Is there any more compelling expression of the human experience than creating something that endures while simultaneously acknowledging our own impermanence?

That’s poetry.

And Randy Leavitt has been writing verse after verse his whole life.

He’s not loud about it. He never has been. But listen closely, and you’ll hear it in the way he bolts a line he knows he’ll never climb. In the way he built a thousand-square-foot climbing gym in his garage, years before anyone knew what “training culture” even was. In the way he mapped foreclosure listings with the same attention he used to study unclimbed rock.

Randy has always played the long game.

And the long game isn’t glamorous. It’s built on deferred gratification, repeated effort, and quiet preparation. It’s made of maps pinned to walls, trips driven in silence, bolts drilled in solitude. It requires belief, not just in your own potential, but in the possibility that someone else will come along and finish what you started.

In 1994, Randy bolted a route on the upper tier of Clark Mountain. He could climb parts of it. He could envision the line. But he knew the whole thing was beyond him. He bolted it anyway.

Fourteen years later, Chris Sharma sent that route and named it Jumbo Love. It became the most difficult rock climb in North America. A milestone, yes. But more importantly, a moment that revealed Randy’s real gift: not athleticism, not entrepreneurship, but vision.

That kind of vision doesn’t come from ego. It comes from something else, something slower and more enduring. A kind of patience. A kind of humility. A kind of faith in the unfolding of time.

Randy’s real estate career followed the same rhythm. While others chased quick flips, Randy played the long arc. He studied tax records and shadow patterns. He built recurring income instead of fleeting highs. And then he funneled that freedom right back into his climbing. Into first ascents. Into new areas. Into lines he might never finish, but someone would.

That’s the thread that runs through his life. And I would argue, through all lives that matter.

Because the long game isn’t about winning, it’s about building something solid enough to hand forward. Something rooted in process. Something shaped by integrity. Something that might still be standing long after you’re gone.

And it’s not just about routes or buildings. It’s about how we parent. How we lead. How we train. It’s about doing the hard work now so someone else’s path is smoother. It’s about leaving signposts behind you and trusting someone will follow them, even if they never know your name.

There’s a quiet beauty in that.

And a radical honesty, too.

In a world addicted to speed, Randy’s life is a reminder that some things are only revealed over time. That legacy isn’t built in loud moments, but in the slow accumulation of years. And that the deepest kind of fulfillment might just come from finishing the work no one else even sees.

That’s the poetry of the long game.

And it’s a poem worth writing.