289 - Why Fear Stops Us From Winning (A True Story)
Fri Feb 06 2026
In this inspiring episode, Monica shares a powerful story from her son’s middle school basketball game that mirrors a truth many entrepreneurs overlook: regret hits harder than failure. Through a deeply personal lens, she explores how fear of judgment, not failure, holds us back from our greatest opportunities...in business and in life. Whether you’re sitting on a bold idea, hesitating to launch a product, or unsure how to take the next step, this episode will push you to move forward, even if you’re not sure what the result will be. Because progress doesn't come from perfection, it comes from action.
Episode Quote: I've missed more than 9,000 shots in my career. I’ve lost almost 300 games. I’ve failed over and over and over again in my life. And that is why I succeed. ~ Michael Jordan
What You Will Learn in This Episode:
How to overcome fear of judgment that keeps you stuck
How to use missed opportunities as learning tools
How to build real confidence without waiting for validation
How to reframe rejection and missed chances in business
How to encourage yourself (and others) to keep showing up
Sign up for the Level Up Living Newsletter
KICKSTART YOUR BUSINESS PROGRAM
Monica FREE ebook
Get your Become Your Own Boss Planner
Ways to reach Monica:
Instagram: @becomeyourownbosspodcast
Email: monica@monicaallen.com
Listen now to find the courage to take your shot.📱 Don’t forget to subscribe and leave a review on Apple or Spotify—your support means everything.
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In this inspiring episode, Monica shares a powerful story from her son’s middle school basketball game that mirrors a truth many entrepreneurs overlook: regret hits harder than failure. Through a deeply personal lens, she explores how fear of judgment, not failure, holds us back from our greatest opportunities...in business and in life. Whether you’re sitting on a bold idea, hesitating to launch a product, or unsure how to take the next step, this episode will push you to move forward, even if you’re not sure what the result will be. Because progress doesn't come from perfection, it comes from action. Episode Quote: I've missed more than 9,000 shots in my career. I’ve lost almost 300 games. I’ve failed over and over and over again in my life. And that is why I succeed. ~ Michael Jordan What You Will Learn in This Episode: How to overcome fear of judgment that keeps you stuck How to use missed opportunities as learning tools How to build real confidence without waiting for validation How to reframe rejection and missed chances in business How to encourage yourself (and others) to keep showing up Sign up for the Level Up Living Newsletter KICKSTART YOUR BUSINESS PROGRAM Monica FREE ebook Get your Become Your Own Boss Planner Ways to reach Monica: Instagram: @becomeyourownbosspodcast Email: monica@monicaallen.com Listen now to find the courage to take your shot.📱 Don’t forget to subscribe and leave a review on Apple or Spotify—your support means everything.