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June 2, 2025 43 mins

In this episode, we’re talking about how to know when it’s REALLY time to go. Not when your manager makes it unbearable, not when the reorg finally hits, but when YOU decide that staying is costing more than it’s worth.

We break down the three questions that have helped us walk away from “good” jobs and build a better life on the other side. We talk about what your job is teaching you (even when you’re not paying attention), how to tell if you have any say in your future there, and why asking “would I say yes to this job today?” might be the cleanest filter of all.

You’ll also hear:

  • The truth about paper-pushing, middle management, and the skill sets that aren’t really transferable
  • Why some jobs don’t just feel like relationships, they are emotional traps
  • How to rebuild self-trust before you make your next move
  • What it means to leave with your dignity intact and why that’s the real win

If you’re at a career crossroads or know someone who is, this one’s for you.


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