
250. Failure, Comparison, and The Bitter B Trap
From Hint of Hustle with Heather Sager by Heather Sager
May 12, 2026 · 40 min · Episode 250
About this episode
Heather Sager discusses the subtle feelings of failure and comparison that many entrepreneurs experience.
You're not failing. But I'd bet good money you walk around feeling like you are. I’m not talking about the obvious kind of failure… a flopped launch or a missed goal… today we’re talking about the quieter kind of failure: A low-grade hum of "I should be further along by now." The spiral that starts the second something doesn't go the way you planned. The way you measure your right-now self against the highlight reel of your past self AND the fantasy version of your future self, simultaneo...
People in this episode
Host: Heather Sager
Topics covered
- failure
- comparison
- self-improvement
- entrepreneurship
- mindset
Keywords
- failure
- comparison
- entrepreneurship
- mindset
- self-improvement
- goals
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