My Favorite Mistake — 188: Simon T. Bailey Was Too Honest with a Reporter While a Disney Executive

Keynote speaker, author, coach, and more

Episode page with video, transcript, and more

My guest for Episode #188 of the My Favorite Mistake podcast is Simon T. Bailey. He’s a keynote speaker, a success coach, an author, a television host, and philanthropist — he has worked with over 2,000 companies in 50 different countries.

SUCCESS magazine calls Simon one of the top 25 people who will help you reach your business and life goals.

He’s the author of books including Release Your Brilliance: The 4 Steps to Transforming Your Life and Revealing Your Genius to the World and his most recent book, Ignite the Power of Women in Your Life – A Guide For Men.

Before starting his company, he worked for the Walt Disney Company, including four years as the Sales Director for the Disney Institute. His degrees include a master’s from Faith Christian University and three honorary doctorate degrees.

His main website is and his book’s website is

In this episode, Simon tells his favorite mistake story from his time as a Disney executive. Why did he violate the rule of “never talk to the media unless authorized” — and why did his boss ask “what were you thinking?” Was that “career suicide” or did it “change the trajectory” of his future? What can we learn from his experience?

We also talk about questions and topics including:

  • Your career transition?
  • Tell us about your latest book, Ignite the Power of Women… what was the spark that led to it?
  • How much do men need to help vs. getting out of the way?
  • Why do you say this is now “the age of the woman”?
  • “Coaching is not telling, it’s asking”
  • You say gender equality benefits everyone… how does gender equality benefit men?
  • Intersectionality — Different support for a woman of color?
  • You wrote that it took 3 years to write the book — ten drafts, 3 title changes… tell us more about that journey and bringing it to the finish line?
  • Your next book?
  • Tell us a little bit about a non-profit that you support, Global Servants and what they do…

Find Simon on social media:

Support this podcast: