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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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Ever wonder why you stall right when things start working?
You might not be afraid of failing — you might actually be afraid of succeeding.
In this episode, Jen Laffin unpacks one of the most overlooked mindset blocks in entrepreneurship: the fear of success. She explains how your primal brain — the part that’s wired to keep you safe, alive, and lazy — often mistakes success for danger because it means change, visibility, and responsibility.
When your brain equates growth with risk, it quietly steers you back to what feels familiar — what Jen calls your Comfort Cave.
This conversation will help you spot how fear of success hides behind perfectionism, procrastination, and over-preparing — and show you how to rebuild the self-trust needed to confidently expand into your next level.
💡 What You’ll Learn in This Episode
- What the fear of success really is — and why your brain sees it as a threat
- How it shows up in your business disguised as productivity or “getting ready”
- The identity shift success requires and why that can feel uncomfortable
- Four reflection questions to help you recognize if fear of success is keeping you stuck
- How to build capacity for success instead of trying to eliminate fear
- Why self-trust is the bridge between who you are now and who you’re becoming
Fear of success keeps capable entrepreneurs looping in maintenance mode — refining, preparing, and perfecting — instead of expanding.
When you understand that your hesitation isn’t laziness but protection, you can lead yourself through it instead of letting it lead you.
Thank you for listening!
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Want more?
- Identify the exact activities that generate revenue in your business and make time for them. Download your free Productivity Playbook here.
- Looking for accountability support to get your hard things done? Learn about the Goal Getters Club here.
- Visit Jen's website by clicking here.
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