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September 16, 2025 13 mins

Welcome to a solo episode on the fear of starting over.


I talk to people for a living, here on the pod but also in my coaching and speaking career.  And in virtually every conversation, I talk to people that want to do something new.


And it’s scary as hell.


But in these conversations, something new emerges.  It’s this fear of judgment that so many guests have talked about here on the podcast.  So is it really your fear of starting over that’s holding you back, or is it the fear of people seeing you start over?


This topic has been a lightning bolt to the chest for me.  So let’s talk about what it really is that’s holding us back, and I’ve come up with 3 specific habits we can build to move through it, and live the bigger life we deserve.


Key Takeaways


  • Most of us aren’t afraid of starting over—we’re afraid of people seeing us start over.
  • What feels like a huge leap to you might look like a natural next step to everyone else.
  • Stories from past guests like Sensi Graves, Karl-Allen Muncy, PrettyLynne, and Greg Boyd remind us that reinvention is possible—and powerful.
  • Confidence doesn’t come before action—it comes from action. The second time is always easier than the first.
  • Try the Alyx Parks exercise: ask people how they’d describe you to someone else. It’s a humbling, inspiring way to see what others already believe about you.
  • Judgment—especially self-judgment—is often the thing holding us back. As Sylvia Baffour says, start by writing for yourself and acting before you feel ready.
  • The world sees more in you than you probably see in yourself. Let that build your conviction. Confidence will follow.


Connect with Bob Mathers

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Recommended Episodes

She’s Like the Wind with Sensi Graves

It’s Not Too Late to Create a Career You Love with Alyx Parks

Curiosity, Creativity & Connection with Sylvia Baffour

Throttle Therapy with Karl Allen-Muncey

What the Fxck are You Waiting For? With Greg Boyd

PrettyLynne: Soft Porn, Courage, Judgment and Finding Yourself




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