True Things I Cannot Prove (But You Know They're True Too)
If a private club doesn’t identify and empower its next generation of leadership — while the current leaders are still in the room —
that club will begin to drift within five years, and unravel within ten.
I can’t prove it. But I’ve seen it.
We’ve all seen it:
The club that lives off legacy until legacy becomes a liability.
The one that talks about “next-gen members” but makes every decision for last-gen comfort.
The club that finally decides to modernize… five years too late.
Here’s what I’ve learned from 30 years in the room:
The healthiest clubs are led by people who think in decades, not seasons.
They make decisions that may not be fully appreciated today, but will be vital tomorrow.
Their time horizon is long.
And that — more than budget, board makeup, or amenities — is what separates the thriving from the fading.
Average clubs think in fiscal years.
But the average member?
They think in lifecycles. In family chapters. In future memories.
And the clubs that earn their loyalty are the ones that plan for that future — not just the next two initiatives.
Years ago, I heard a radio interview about self-made millionaires. Theinterviewer asked:
Is it IQ? Education? Family money? Connections? Luck?
Answer: No. None of the above.
The common threads?
- They’ve failed — often publicly.
- They think there’s a better way.
- They keep going anyway.
- They think further ahead than most people do.
Time horizon predicts altitude.
The longer you’re willing to look ahead,
the higher you’re able to rise.
So what does this mean for club leaders?
It means stop asking:
“What will this do for us this year?”
Start asking:
“What are we building for five years from now?”
“Are we earning the reputation our next generation will inherit?”
And most importantly:
Don’t let a waitlist lull you into silence.
A waitlist is a snapshot — real, but temporary.
It tells you who’s interested now, not who will still care two years from now.
If you're not actively telling your story, someone else is.
Marketing is what keeps the story alive.
Even with a multi-year waitlist, you have to keep showing up.
Because the world changes. Economies shift. Priorities evolve.
And nothing erodes momentum faster than assuming you don’t need to earn it anymore.
Waitlists come and go.
Brands endure — but only if you keep feeding them.
Until next Monday,
