#274 Turning Rejection Into Redirection w/ Simon Bailey

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This week on the Wealthy Wellthy Podcast, I am thrilled to introduce internationally-recognized speaker, author, and expert on human potential, Simon Bailey. 

In this candid conversation, Simon shares how he overcame incredible challenges to transform his life…several times. He talks openly about overcoming adversity AND suicidal thoughts in his youth. You’ll learn about the impact that one of his teachers had on him, propelling to beat all odds to become senior class president! 

Now an internationally-recognized speaker, author, and expert on human potential, Simon sat down with me to share his powerful journey and wisdom.

We discuss the huge risks he took by quitting multiple corporate jobs in his 30s to completely reinvent himself. Though it felt like “career suicide” at the time, Simon knew he needed to make significant changes in his life to find himself and pursue his true passion. He bet on himself – even without a safety net – and that bet paid off!

Takeaways I Got From This Episode Were:

  1. Believing in others, especially youth, can change the trajectory of their lives. A little encouragement goes a long way.
  2. It’s never too late to reinvent yourself and transform your life. You can pivot at any age.
  3. Surround yourself with mentors who see more potential in you than you see in yourself. Their belief can pull you higher.
  4. Come from a place of service. It’s about lifting others up, not getting something from them.
  5. You always have a choice in how you respond to adversity. You can choose to thrive.

Here Are Five of My Favorite Quotes:

  1. “You have to embrace unqualified readiness. And I said what’s unqualified readiness? He said if you want to grow, you take the micro step in front of you. And then the next step will reveal itself and then the next step will reveal itself.”
  2. “When I come from a place of abundance, I talk less and I listen more, because it’s in listening that I begin to discover the avenues of opportunity that are opening up right before my very eyes.”
  3. “When you come from a place of being hopeful. What you realize is that a helpless person is a hopeless person, but a hopeful person is a helpful person.”
  4. “Until you reach a woman’s mind you’ll never touch her heart.”
  5. “The light No, it’s real. Yes. George Floyd happen. Yes, Michael Brown happened. Yes, Briana Taylor happened. And yes, it’s out there. But how do I show up in my little patch of the corner of where I’m at, and be the best human being that I can be even if the forces of darkness are working against me?”

Time Stamps:

  • [01:07] Simon Bailey shares his inspiring personal journey of overcoming adversity and finding his purpose in motivational speaking and coaching.
  • [10:00] He discusses the pivotal moment when a teacher believed in him and how that changed his trajectory.
  • [25:38] Simon talks about committing “career suicide” at Disney and reinventing himself as an entrepreneur.
  • [31:01] He explains his approach of serving others and how that positive energy impacts people.
  • [37:02] Simon discusses the importance of coaches and mentors for success and fulfillment.
  • [42:49] He shares insights from his book “Ignite the Power of Women” on being an empowering partner.
  • [56:49] Simon busts the myth “that as a black man, you cannot make it in America.” Through his own success, he proves everyday choices and positive mindset allow you to overcome challenges and discrimination.

Simon’s Myth Buster

One of the big myths or norms that Sam wants to dispel is the idea that people often express of just trying to “get through the days.” She heard someone say this at the store recently, and it really bothered her because she believes that every single day counts. In her work, Sam aims to inspire people to think that each day is meaningful and to approach each day with gratitude, not just trying to get through it. Her message is that we shouldn’t let our days drift by without noticing them or appreciating them. Thinking of just getting through the days means our days may “cry” because we don’t acknowledge them or the opportunities within them. Sam’s view is that we should see value in each day and make the most of each one.

Links For Simon :

Simon’s Book “Ignite the Power of WOMEN In Your Life”

Simon’s Website

Connect with him on his socials.



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