January 20, 2026 | Issue Archive
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You Can Live With Failure—But Not Regret
This week I saw a clip of an interview with George Clooney that stopped me in my tracks:
“As you get older, failure is something you can handle. Regret, you can't live with...”
Sit with that for a moment—not as a celebrity soundbite, but as a life principle.
Clooney didn’t say failure was painless.
He said it was bearable.
What’s unbearable is looking back and realizing you never even tried.
Failure tells a story of effort.
Regret tells a story of absence.
And that distinction matters more than we realize.
The Trap We Fall Into
Most of us don’t avoid action because we’re lazy.
We avoid it because we’re afraid.
So we ask:
What if I fail?
Instead of:
What if I never try?
We tighten our grip on what’s familiar.
We choose predictability over possibility.
We call it “being realistic,” when really, it’s self-protection.
But here’s the uncomfortable truth:
What feels safe today can quietly turn into a cage tomorrow.
Failure feels like a wound.
But wounds heal—and often become wisdom.
Regret lingers differently.
It hangs around like an unfinished story you never gave yourself permission to write.
This Ends Now
Here’s the ending that changes everything:
The belief that playing it safe will protect you.
It won’t.
It only delays the reckoning.
An ending is a threshold. It forces a choice:
Do I step into the unknown, even if I stumble?
Or do I stay here, in the half-realized version of myself?
That’s the real question behind failure versus regret.
Failure says:
I tried. I learned. I grew.
Regret whispers:
I didn’t try. I’ll never know.
If you’re honest, you already know which one costs more.
This Moment Matters
So let’s bring this down from philosophy to practice.
Ask yourself—today, not someday:
What risk am I avoiding?
A project. A conversation. A calling I’ve postponed.
What ending am I resisting?
An identity. A comfort zone. An old agreement with fear.
When I imagine my future self looking back…
Which version feels lighter?
Then take one step forward.
Not perfect. Not polished. Just honest movement.
Small actions rewrite big stories.
Here’s one question I’ll leave you with this week:
Would you rather live with fear—or freedom?
Because failure, with all its mess and wobble, still puts you in the arena.
Regret keeps you on the sidelines.
And when your story unfolds into what it was always meant to become, you won’t be grateful you played it safe...
You’ll be grateful you tried.
Up we go—