The Biggest Career Mistake Successful People Make

Podcast Archives - Dale Callahan · Jul 23, 2026

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Episode 255 | Watch on YouTube | Listen on Buzzsprout

It’s 9:40 on a Tuesday night, and David is sitting in his truck in his own driveway. Engine off. He’s not ready to go inside yet. He just got off a call with his fourth boss in three years, explaining a reorg that folds his team into someone else’s org chart — no new title, no new pay, just another person to prove himself to.

Twenty-two years of experience. A team that hits its numbers every quarter. And he still feels like he has to earn his spot in the room every few months…