SEEING THE FIELD
What Makes Sammy Run?
Ambition is a powerful engine.
It can pull you out of dark places.
It builds careers, wealth, and can make us better people.
But once you’ve pulled yourself out of that burning basement, that ambition engine which once saved us, can start to become a liability.
There comes a point when a man realizes he’s been running for a long time.
The job got bigger.
The house got nicer.
The achievements piled up.
And somewhere along the way, he forgot to enjoy it. There was always a better place to work towards. The present sacrificed to get that better place.
Then, beneath the surface, quiet questions creep in:
When have you arrived? When can you stop sacrificing your present enjoyment of the moment you built? Is the juice still worth the squeeze?
But for high achieving men, that engine can be hard to simply turn off.
And once you see what makes that ambition engine run on overdrive. Once you peel back the layers, you see it’s fueled by:
Scarcity. Shame. A place they can never return to; a home that never was, love they never received.
So for those who had to fight their way out. Once you’re safe and have “made it,” there’s a harder question: is it even possible to shut this off before it tarnishes the things that matter most?
Because if winning is the only way you know how to live, there’s no such thing as enough.
We see the story everywhere.
Sammy Glick claws through Hollywood in What Makes Sammy Run?
Don Draper builds a life he can’t feel. A Self, and the love of others, he can’t accept.
The lone skier in Downhill Racer, chasing gold at the cost of everything human.
Men who achieved what they thought would save them.
And still found the emptiness waiting on the other side.
This Week Inside The Magnolia League
The Archives — Don Draper, trauma, and when ambition becomes armor instead of freedom.
The Next Frontier — “The Three Games of Life,” all of which are here to help us grow, evolve and get closer to accepting our own death.
The Clubhouse — This golf visionary, you’ve likely never heard of, and the empire he’s building on the edge of the world.
The Lodge — A poem about the moment ambition stops fitting — and life asks you to move differently as the seasons change.
The Joint — Old Hollywood & The California Sound — the dream, the glow, and the darkness that exists beneath the glamorous facade.
The Pro Shop —Three classic books on Hollywood ambition, reinvention, and the machinery of success.
People. History. Timeless Classics.
THE ARCHIVES
The Real Lessons From Mad Men
Most casual viewers think Don Draper is the man.
The swashbuckling ad man confidence. The money. The women.
But Mad Men isn’t an aspirational story.
It’s a cautionary one.
Don didn’t reinvent himself to become successful.
He reinvented himself to escape shame.
Even after he builds a beautiful life, he can’t feel it.
He’s running from:
Being exposed
Abandonment
The fear that he’s unlovable
Sex and booze become a mediator. A way to temporarily quench the desperate thirst for human intimacy without the fear of abandonment. Meanwhile he’s pushed away anyone who’s ever truly loved him.
Mad Men showed us the conditions under which trauma and shame are born and, if you view the show’s ending from a “glass half-full” lens, what is needed for healing.
At Eslen, the therapeutic community beside the Pacific Ocean, a spark of life ignites in Don while listening to Leonard—a sad man in the therapy circle, describing the pain of his loneliness and inability to accept love. Don knelt down next to Leonard and they embraced while sobbing. Don’s despair, finally witnessed by himself and others, lifts and liberates his soul.
Don, like all of us, needed to feel safe and accepted by at least one other person in order to heal. I’d like to envision Don beginning a new life. Landing the Coke account and creating one of history’s greatest ad campaigns. The road will continue to be rocky. But this time, he ain’t alone. We exist in connection and cease to exist without it.
Two moments worth revisiting:
The Hershey Pitch — Don finally reveals his truth, and the room finally sees the damaged boy behind the mask.
Leonard (therapy circle) — the moment Don recognizes the loneliness he’s been outrunning his entire life, and the love he couldn’t receive because he couldn’t recognize it in the first place.
Philosophy. Improvement. Growth.
THE NEXT FRONTIER
The Three Games of Life
Most of us spend our early years playing the first two games.
Game One: The Game of Survival
Security. Stability. Finding your next meal.
Game Two: The Game of More
Achievement. Status. Accumulation.
But there’s a third game most high performers eventually run into — usually after they’ve won the first two.
Game Three: The Game of Meaning
Contribution. Alignment. Legacy. Spiritual Health.
Not just winning — but asking whether the game you’re playing is still worth playing.
Sporting. Golf. Outdoors.
THE CLUBHOUSE
Building a Golf Empire on the Edge of the World
Most golf development follows the same formula: prime land, templated luxury homes, predictable returns.
Ben Cowan-Dewar took a different path. And he’s perhaps the most influential person in golf you’ve never heard of.
Ben has been quietly executing a very interesting strategy - he finds strips of land in remote corners of the world and turns them into incredible golf courses.
Remote coastlines. Harsh terrain. Places no developer wanted.
Inspired by Bandon Dunes’ template - applied to Cabot Cliffs, Norway, and beyond – his philosophy was simple:
Build something great, even if it’s inconvenient.
Trust that people will come for the experience.
It’s a reminder that the best work often happens when you stop optimizing for scale and returns.
Ben Cowan-Dewar is playing for meaning.
Travel. Culture. Connection.
THE LODGE
A Man Out of Season (A Poem)
There comes a season when the pace that once defined you no longer fits.
The urgency fades.
The noise quiets.
And what once felt like momentum begins to feel like motion without direction.
This short poem captures the quiet tension many driven men experience — the strange feeling of being successful, capable… and somehow out of sync with the life they’ve built.
It’s not burnout.
It’s transition. Just like the seasons.
And sometimes the most important work of a life isn’t pushing harder — it’s learning how to move differently.
Music. Storytelling. After Hours.
THE JOINT
Playlist: Mid-Century Hollywood & The California Sound
California has always sold a dream — sunshine, reinvention, freedom.
Light up your swinging mid-century modern pool party in the hills with songs that brought the idea of California to the world.
From old Hollywood glamour, to Beach Boys surf riders, and the rock ‘n roll of Topanga Canyons counter-culture revolution and the Sunset Strip.
Products. Brands. Craftsmanship.
THE PRO SHOP
The Best Books on Hollywood: The Machine of Ambition
The original story of ruthless ambition. Sammy Glick claws his way through Hollywood with talent, speed, and zero loyalty — a portrait of success achieved at the cost of your the soul (and what’s driving it all).
A legendary producer’s rise, fall, and improbable comeback. Part memoir, part Hollywood myth, Robert Evans captures the intoxicating highs of power, fame, and reinvention — and the fragility behind it all.
The inside story of Creative Artists Agency (CAA), the firm that reshaped modern entertainment. A fascinating look at how influence, relationships, and strategic power — not just talent — became Hollywood’s real currency.
A Final Note
THE LAST WORD
“For what does it profit a man to gain the whole world, and forfeit his soul?”
Written from the American South.
