Why Smart People Still Fail (The $75,000 Mistake Nobody Talks About)

Failure isn't one thing. It's basic, complex, or intelligent — and knowing which kind you're in changes how you recover from it. Most people never learn the difference, so every setback feels like the same verdict on who they are. In this episode, Tom and Michelle draw on 60+ years of combined executive experience to break down the research behind failure, then get personal — sharing the real, unfiltered stories behind their own biggest ones. Michelle opens up about a cross-country career move that collided with a family crisis and left her questioning everything. Tom walks through the $75,000 decision that nearly ended a company he built — and the moment a stranger's honesty forced him to face it. Along the way, they get into why ego keeps people from asking for help, the trait that separates leaders who rarely fail from everyone else, and why the companies that hide failure lose more than the ones that talk about it. If you've ever wondered whether a setback means you're falling behind, this conversation will change how you see it. 00:00 – Trailer 00:56 – Michelle Introduces the Episode 01:27 – The 3 Types of Failure: Basic, Complex, Intelligent 02:49 – Michelle's Story: The Move, the Stroke, the Breaking Point 07:20 – The Lesson: "Only Three Doors Open in Your Life" 09:56 – What Growth Actually Costs You 12:10 – The Stat: Why 50% of New Leaders Stall 12:56 – Roadblocks, Ego, and Why We Don't Ask for Help 14:26 – Tom's Story: The $75,000 Failure 17:37 – The Focus Group That Exposed the Truth 20:55 – Closing the Company and Learning to Grieve 22:36 – Why It's Okay to Get Emotional About Failure 26:57 – The #1 Trait of People Who Rarely Fail 28:17 – Emotional Stability, Self-Awareness, and Leadership 31:15 – Where Companies Still Get This Wrong 32:56 – Final Takeaway 🎙 New episodes every week. 🌐 Learn more: https://strategyrealtime.com 📱 Follow us: https://www.instagram.com/strategyrealtime/ 🎧 Listen on Spotify: https://open.spotify.com/show/2DfbciLHav3DpiaMQmn7WW 🎧 Listen on Apple Podcasts: https://podcasts.apple.com/ke/podcast/strategy-real-time/id1880223593