TB9, S13, E14: Author Cal Callahan — When Success Isn't Enough episode artwork

EPISODE · Jul 14, 2026 · 48 MIN

TB9, S13, E14: Author Cal Callahan — When Success Isn't Enough

from The Back 9 - Midlife, Best Life.

Cal Callahan had everything he'd spent years chasing: a successful career, a beautiful family, and all the outward signs that he'd made it. The problem was...he still wasn't himself. In one of the most vulnerable conversations we've ever had on The Back 9, Cal shares the deeply personal journey behind his new book, UNLEARN—and, for the first time, why he's bringing his 6½-year podcast, The Great Unlearn, to a close. This is the only podcast appearance he's making to talk about the book. Together, we explore what happens when we stop trying to become more and start letting go of the stories, expectations, and identities that no longer fit. Along the way, Cal opens up about the moment his wife saw something in him he couldn't yet see in himself—and why that changed everything. If you've ever reached a point where success still left you searching, this conversation may help you discover what you've really been looking for...on the Back 9.

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TB9, S13, E14: Author Cal Callahan — When Success Isn't Enough

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