There’s a moment in an interview between Jerry Seinfeld and Howard Stern where Seinfeld offers a line that has been rattling around in my head ever since author Dan Pink mentioned it in a recent MEA workshop:
“The blessing in life is when you find the torture you’re comfortable with.”
It’s funny. It’s uncomfortable. And it’s strangely liberating.
Because embedded in that line is a truth we don’t often admit: there is no life without friction. Every path—every calling, every relationship, every meaningful pursuit—comes with its own form of strain.
What’s fascinating is the word torture itself. It comes from the Latin tortura, rooted in torquere, meaning “to twist.” Not just pain, but a kind of pressure that bends, contorts, reshapes.
That hits differently.
Because the right kind of “torture” doesn’t just hurt—it transforms.
Leading MEA has always been that kind of chosen twist for me. The privilege of helping people navigate midlife and meaning is real. But so is the weight of it—the responsibility, the constant evolution, the emotional labor of staying present to other people’s turning points.
And now, layered on top of that, is cancer. Three months ago, I wrote this post on Tending My Calling While Treating the Cancer. That’s what I’m doing starting this Thursday when I start targeted radiation again for my stage-3 prostate cancer that has spread to the lymphs around my abdomen, while also starting Orgovyx again, a form of pharmaceutical castration that suppresses my testosterone and gives me many of the side effects of menopause.
If I’m honest, this is not a torture I would have consciously chosen. But it is one I am now being asked to be in relationship with. And like any deep twist, it is reshaping me—my pace, my priorities, my sense of what matters.
Here’s what I’m learning:
The blessing isn’t in avoiding life’s twists.
It’s in recognizing which ones feel…aligned.
Even now, I wouldn’t trade this life for a more comfortable, less meaningful one. I wouldn’t trade purpose for ease. I wouldn’t trade connection for detachment.
Because the alternative to “comfortable torture” isn’t peace.
It’s numbness.
So maybe the real question isn’t:
“How do I eliminate the hard things in my life?”
But:
“Which tensions are worthy of me?”
Somewhere between purpose and pain—between the stretch and the strain—is where a life begins to feel not just endured, but chosen. I am doomed to be stewarding hope…and that’s just fine.
How might you organize your life with a view to your heavenly legacy?
-Chip