How To Overcome the Fear of Failure & Feeling Stuck | CEO Wynne Leon episode artwork

EPISODE · Mar 3, 2026 · 36 MIN

How To Overcome the Fear of Failure & Feeling Stuck | CEO Wynne Leon

from What Do You Know To Be True? · host Roger Kastner

What if you could stop waiting for the “perfect plan” and start building your next chapter one smart experiment at a time?For a lot of proven leaders, coaches, and consultants, that constant need to “get it right” turns into overthinking and the feeling of being stuck. This conversation offers a practical way to move from overthinking to intentional trying without blowing up the life you’ve already built.I’m joined by Wynne Leon, whose superpower is being a very good trier. She shares how changing your mindset from creating big perfect plans to testing small experiments can be the fast track for personal development.As the CEO of her own consulting company, an amateur mountain climber, and the host of the “How to Share” podcast, Wynne demonstrates the courage it takes to boldly try new things. You’ll hear how Wynne…➡️ uses structured trying, that is one change at a time, ➡️ documenting what happens, and ➡️ “undoing” when it doesn’t work…to turn big, scary changes into a series of small, reversible moves. We talk about the difference between reckless risk and calculated experiments, how to know when to turn back (her mountain “turnaround time” principle), and why you don’t actually need certainty to move forward.If you’re ready to trade the pressure of having it all figured out for the energy and courage of learning as you go, this conversation is your invitation. You don’t have to blow everything up to become more of your true self. You can try, reflect, learn, adjust, repeat.In this episode, Wynne answers the following questions:➡️ How to create small experiments for personal growth?➡️ How to create a personal development plan?➡️How to create a safe growth plan?➡️How do you figure out your next step in life?Resources mentioned in the episode: ➡️Wynne’s LinkedIn: https://www.linkedin.com/in/wynneleon/➡️How to Share podcast: https://open.spotify.com/show/0qInZdzg1Xn3Xac1IMh2z0?si=5e910a4419784495Music in this episode by Ian Kastner."What Do You Know To Be True?" is an invitation to be inspired to become more of your possible self by discovering your superpower, unlocking your potential, and creating your impact in the world. This podcast is for leaders, coaches, org development practitioners, and anyone who works with people who want to be inspired to discover their superpower, unlock their possibilities, and make meaningful impact in the world. For more info about the podcast or to check out more episodes, go to: https://whatdoyouknowtobetrue.com/"What Do You Know To Be True?" is hosted by Roger Kastner, is a production of Three Blue Pens, and is recorded on the ancestral lands of the Duwamish and Suquamish people. To discover the ancestral lands of the indigenous people whose land you may be on, go to: https://native-land.ca/Keywords#burnout #perfectionism #overthinking #FearofFailure #mindset #personaldevelopment

What if you could stop waiting for the “perfect plan” and start building your next chapter one smart experiment at a time? For a lot of proven leaders, coaches, and consultants, that constant need to “get it right” turns into overthinking and the feeling of being stuck. This conversation offers a practical way to move from overthinking to intentional trying without blowing up the life you’ve already built. I’m joined by Wynne Leon, whose superpower is being a very good trier. She shares h...

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How To Overcome the Fear of Failure & Feeling Stuck | CEO Wynne Leon

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This episode was published on March 3, 2026.

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What if you could stop waiting for the “perfect plan” and start building your next chapter one smart experiment at a time?For a lot of proven leaders, coaches, and consultants, that constant need to “get it right” turns into overthinking and the...

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