Latest / Company of One with Dale Callahan
Why Promotions Feel Like Progress But Aren’t #230
Promotions are often treated as the ultimate measure of career success.
More responsibility.
More income.
More stability.
Yet many high-performing professionals reach a point where promotions no longer feel like progress.
In this episode of Company of One, Dale Callahan challenges traditional career advice and explains why promotions frequently increase dependence rather than freedom. He breaks down how career advancement can narrow optionality, reduce leverage, and lead to a quiet career stall — even for capable, motivated professionals.
This episode covers:
Why promotions don’t always lead…
The skinny
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