What happens when your lifelong dream shatters at 22—and you’ve got no Plan B? In this raw and real conversation, Matt sits down with Damon Lembi, former pro baseball player turned CEO of Learnit, to explore how identity, leadership, and imposter syndrome collide in high-stakes moments. Damon unpacks the four-step framework he built to overcome self-doubt—Label Your Fear, Work Hard, Practice Deliberately, Learn and Let Go—and shares how it’s helped him evolve from hitting home runs in the College World Series to upskilling over 2 million professionals globally. With vulnerability, grit, and a healthy dose of humility, Damon reveals how failing publicly, receiving tough feedback, and embracing setbacks have been the fuel behind his leadership journey. Whether you’re a CEO, entrepreneur, or ambitious professional, this episode is your playbook for turning adversity into mastery—and doing it with integrity.Chapters:<ul><li>00:00:00 - Kicking Off with Eternal Optimism</li><li>00:00:29 - Meet Damon Lembi: From Dugout to Boardroom</li><li>00:01:28 - Baseball Dreams, Big Setbacks</li><li>00:05:28 - When Self-Doubt Takes the Mound</li><li>00:10:04 - The 4 Steps That Saved My Confidence</li><li>00:16:03 - From Receptionist to CEO: Earning It the Hard Way</li><li>00:23:08 - The Diagnosis That Changed Everything</li><li>00:23:48 - Losing Vision, Gaining Clarity</li><li>00:24:37 - Brotherhood, Mentors, and Support That Stuck</li><li>00:25:01 - Leading with Humility (and Hair Gel)</li><li>00:28:06 - Why Podcasting and Connection Fuel Growth</li><li>00:32:02 - Must-Read Books for Real Leaders</li><li>00:39:31 - Music, Memories, and the People Who Shape Us</li><li>00:43:30 - Final Wisdom and a Hopeful Sendoff</li></ul> Links And Resources:<ul><li><a href="https://learnit.com" rel="noopener noreferrer" target="_blank">Website</a></li><li><a href="https://www.linkedin.com/in/damonlembi/" rel="noopener noreferrer" target="_blank">Damon Lembi on LinkedIn</a></li></ul> Thanks so much for joining us this week. Want to subscribe to Eternal Optimist? Have some feedback you’d like to share? Connect with us on <a href="https://podcasts.apple.com/us/podcast/the-eternal-optimist/id1623530310" rel="noopener noreferrer" target="_blank">iTunes</a> and leave us a review!

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