My Favorite Mistake: Learning Without Blame in Business and Leadership

Kate Lowry, author of Unbreakable, shares the early-career mistake of reporting workplace misconduct without the sophistication to make it land -- and got punished for it. A candid conversation on recognizing fear-based leadership and protecting your agency when you’re stuck under it.

Joe Hennes of Tough Pigs on the mistake of getting hired at his dream company, Sesame Workshop, and being laid off years later. A candid look at the cost of turning fandom into a career.

Jesse Jackson, contact center leader and host of Set Lusting Bruce, on the mistake of going gun-shy as a new leader when veterans push back with ”we tried that, it didn’t work.” A practical conversation about speaking up, psychological safety, and when to trust your own judgment.

Joel Steele built a healthy fast food chain before he was 25 and watched it collapse into roughly $800,000 of debt. He joins Mark Graban to share what founders miss when they chase growth instead of profit, and how he rebuilt from rock bottom into a successful financial services firm and a book with a $1 million charitable mission.

Andy Freed, CEO of Virtual Inc. and author of Lead Like the Boss, shares how a cross-cultural marketing blunder taught him that communication without audience awareness is just noise -- and what Bruce Springsteen’s set list, stage presence, and end-of-show ritual teach leaders about preparation, energy, and making people feel valued.

Mike Chaput’s favorite mistake was making ”have a sense of humor” a core company value at Endsight -- a choice that permitted blame-based behaviors, including a rubber chicken shaming ritual, until Deming’s principles taught him that humor must be subordinated to respect.

Patrick Engasser spent two years near the bottom of a 615-person sales organization before hiring a coach reversed everything. His lesson for leaders: trial and error is the most expensive education there is -- and you don’t have to pay that price.

MLB is rolling out the Automated Ball-Strike challenge system -- ABS -- for the 2025 regular season. The idea is to reduce bad calls by giving teams two challenges per game to contest ball-and-strike decisions. Get it right, you keep the challenge. Get it wrong, you lose it. It’s a smart design. It’s also a new source of mistakes that didn’t exist before the fix. In this Mistake of the Week, Mark looks at what happens when correcting human error depends on another human decision -- and what one anonymous coach predicted, vividly, about how the pressure of challenge management will play out before the season is over. Technology changes what kind of mistakes get made. It doesn’t eliminate them.

A forgotten water heater tap led to hours of unnoticed leaking — and by morning, a neighborhood street had turned into an accidental ice rink. In this episode of Mistake of the Week, we look at a story from northwest China and ask why the real problem wasn’t human forgetfulness, but a system that required perfect memory. With no alarm and no automatic shutoff, a small oversight spread into a shared community problem. It’s a reminder that learning doesn’t start with blame or shame. It starts by designing systems — at home, at work, and in our communities — that catch small problems early, before they freeze into something much bigger.

Olympic gold medalist Breezy Johnson celebrated her win — and her medal broke. In this Mistake of the Week, Mark Graban explores what happens when systems aren’t designed for real-world behavior — and why it’s better to fix the design than blame the user.

What happens when diesel fuel ends up where it shouldn’t? In this Mistake of the Week, Mark Graban examines a real-world systems failure that left hundreds of drivers stranded after diesel fuel was mistakenly introduced into the gasoline supply in Colorado. Rather than focusing on blame or punishment, regulators emphasized learning, root cause analysis, and prevention. This episode explores why that response matters—and what it teaches us about mistake-proofing, system design, and leadership. A practical reflection on why mistakes are predictable, why upstream errors overwhelm downstream safeguards, and how organizations can respond in ways that actually prevent the next problem.

Amy Rasdal shares her favorite mistake: undercharging for consulting work because of fear. In this episode, she and Mark Graban explore pricing confidence, why accomplished professionals often charge less than they’re worth, and how one “gateway mistake” led to better decisions and long-term growth.

What happens when a business deal looks solid on paper—but falls apart in real life? Episode page with video, links, and more My guest for Episode #335 of the My Favorite Mistake podcast is Kevin Hipes, an entrepreneur, author, and former city commissioner who’s been called the “New York Forrest Gump” because of the many lives he’s lived. Kevin shares the story of one of his biggest—and most unforgettable—business mistakes: buying an oil tanker in the Caribbean. What began as a seemingly foolproof investment with a strong pro forma turned into a cascade of unexpected challenges, including regulatory changes, ethical dilemmas, geopolitical risk, and international drama. In this episode, we talk about: Why smart people still make big business mistakes How external forces can derail even the best plans Learning from failure instead of hiding from it Resilience after financial and emotional setbacks The importance of mental health awareness for leaders and entrepreneurs Kevin’s story is funny, sobering, and deeply human—and a powerful reminder that mistakes don’t define us unless we refuse to learn from them.