The growth paradox | Why leaders who avoid pain need it most | The Best Leadership Podcast For VPs and Managers
  • June 23, 2026

107. The growth paradox | Why leaders who avoid pain need it most

My dentist drilled into my tooth last week, looked me in the eyes, and said something that stuck with me longer than the Novocaine.

“You know, this probably wouldn’t hurt so much if you just stopped fighting it.”

I was annoyed. Then I realized she was right. About my tooth. About my leadership. About pretty much everything I’d been resisting for years.

That’s the growth paradox. Society engineers comfort into every corner of our lives. Memory foam, noise-canceling headphones, food at our door. And yet, the people who avoid discomfort the hardest are the ones who need it the most.

In this episode, I unpack why pain isn’t a bug in the human experience but a feature, the difficult employee who taught me more than any MBA, and the uncomfortable truth that the thing you’re most afraid of is probably the thing you most need to do.

🎧 Press play. Stop fighting the drill.

In this episode:

â–¶ My dentist’s accidental leadership lesson during a routine filling replacement
â–¶ Why society’s obsession with comfort is making us weaker, not better
â–¶ The growth paradox: people who avoid pain are the ones who need it most
â–¶ Dave: the difficult employee who taught me more than an MBA program ever could
â–¶ Why “Dave wasn’t the problem, my ego was” reframed everything
â–¶ Why being a good leader is easy when things go well, and impossible when they don’t
â–¶ The 3-part invitation to discomfort (and how to start tomorrow)

If you’ve been routing around the hard conversation for weeks now, this one’s for you.



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Referenced in this episode:


Show Notes

[00:00] Introduction
[00:47] My Dentist
[02:23] Engineering For Comfort
[03:19] Growth Doesn’t Happen Without Pain
[04:04] The Wisdom in the Discomfort
[05:35] The Growth Paradox
[06:32] Your Invitation to Discomfort


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