May 6, 2026 | Issue Archive
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The Enemy of Long-Term Success
Two events. Two weeks. Two groups of people who reminded me why this work matters.
Last week I was with a tech company bringing together two separate teams after a merger—learning to become one. This week I was with an organization that’s been at it for over a hundred years, currently one of the top-performing companies in its market, and still hungry for what’s next.
I am honored to come alongside groups like these.
(And if you were in one of those groups, welcome to our community!)
Last night, on the plane ride home, I kept thinking about something one of the leaders said...
Here's the situation this second organization I spoke to faces:
Years ago, they went through a near-death experience. Survival demanded change. They had no choice but to adapt—and they did. Beautifully.
Today? Things are going well. Really well.
And now the challenge is harder.
Not because they’re struggling. Because they’re not.
That’s the real tension.
When something is broken, change feels obvious. When something is working, change feels optional.
And that’s exactly where people—and organizations—get stuck.
We wait for:
- the relationship to break down
- the business to decline
- burnout to become unbearable
- life to back us into a corner
Then we change.
But here’s the question Radical Adaptability asks:
What if you chose the ending before life forced it on you?
One of the leaders I spoke with put it this way: “In some ways, this change feels even bigger than the last one.” Not because the company is falling apart. Because they’re trying to evolve before failure requires it.
That’s leadership.
And if I’m honest? That’s also one of the hardest things a human being can do.
Because choosing your ending when survival isn’t demanding it requires something pain doesn’t—it requires vision.
Pain creates urgency. Vision has to manufacture it.
And the greatest threat to long-term success is often short-term success.
Success creates comfort. Comfort reduces urgency. Reduced urgency delays necessary endings. And delayed endings—eventually—create the very crisis we were trying to avoid.
The cycle is quiet. That’s what makes it dangerous.
This Ends Now
The story that says: “If it’s not broken, don’t fix it.”
That phrase has killed more momentum than failure ever has. Because it sounds wise. It sounds measured. It sounds like patience.
But sometimes it’s just comfort wearing a strategy hat.
End the story. Not recklessly. Thoughtfully.
This Moment Matters
Ask yourself—honestly—one question this week:
Is there something I’m keeping that I’d be ending right now… if I were being led by vision instead of comfort?
A process. A habit. A role you’ve outgrown. A way of leading that got you here but won’t get you there.
You don’t have to blow it up. You don’t have to act today.
But name it.
Because the organizations and people who thrive long-term are usually the ones willing to evolve while they still have the strength to do it.
Default is not destiny.
Choose your ending.
Up we go—
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