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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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In this empowering solo episode, Damon Lembi tackles imposter syndrome head-on, drawing inspiration from Oprah’s conversations with icons like Obama and Beyoncé, to moments of his own self-doubt on stage and in the boardroom. Damon unveils his proven four-step framework for overcoming the fear and uncertainty that plagues even the most accomplished professionals. Whether you’re a new manager, a seasoned leader, or someone ready to take your shot at something bigger, this episode delivers actionable advice, practical exercises, and a rallying call to step out of your comfort zone and into your next level.
From labeling your fear to harnessing the power of deliberate practice, this is your roadmap to building confidence, beating self-doubt, and leading with courage.
In this episode, you’ll learn:
- Why even the most successful people struggle with imposter syndrome (and why that’s normal)
- Damon's four-step framework to overcome self-doubt and step confidently into new opportunities
- The power of “purposeful awfulizing” to reframe your biggest fears
- Why action (not just planning) is the secret ingredient to building real confidence
- The role of deliberate practice in mastering new leadership skills
- How letting go and learning from every experience accelerates your growth
Timestamps:
00:00 – Imposter syndrome isn’t a weakness—it’s a human experience
00:40 – Damon’s story: Coaching baseball in his 20s with no experience
01:30 – Learning to lead when you feel unqualified
02:00 – Why confidence often comes after the reps, not before
02:40 – Brené Brown, Jamie Foxx, and others who’ve spoken up about this
03:20 – Reframing imposter syndrome as a signal—not a flaw
04:00 – Lesson #1: You don’t have to be the expert—just be in service
04:30 – Lesson #2: Get radically honest about your fears (then move anyway)
05:15 – Lesson #3: Curiosity beats confidence
06:00 – Lesson #4: Preparation quiets the noise
06:45 – Lesson #5: Talk to yourself the way you’d talk to a friend
07:30 – Damon’s go-to journaling prompt when imposter syndrome hits
08:15 – A challenge to leaders: Name where you're holding back
About Damon Lembi
Damon Lembi is a 3x bestselling author, the host of The Learn-It-All Podcast, and CEO of Learnit – a live learning platform that has upskilled over 2 million people. Drawing from his prior baseball career, Damon brings an athlete’s perspective to leadership. Through his journey, he has gained invaluable insights into what helps organizations grow, how great leaders learn, and why learn-it-all companies outpace their competitors every time.
Resources & Mentions:
- Damon Lembi LinkedIn
- Learnit
- Learn It All Leader (Book by Damon Lembi)
- The Learn-It-All Leader for Kids (Kids Bood by Damon Lembi
- Learnit 45-Day Free Trial for Teams: learnit.com/free
- Learnit Give and Receie Feedback Class
- Learnit Delegation class
- Learnit Listening class
Podcast Contact Information:
Website: www.learnit.com
Email: [email protected]
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