In this episode of My Favorite Mistake, Mark Graban talks with Jason Sherman, an entrepreneur, startup advisor, and educator, about the early startup mistakes that quietly shape everything that follows.

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Jason shares hard-earned lessons about choosing co-founders, distinguishing “smart money” from money alone, and why MVPs should accelerate learning rather than encourage overbuilding. The conversation explores judgment, incentives, and alignment through a Lean lens — showing how optimism, unchecked assumptions, and unclear decision rights can undermine even strong ideas.

This episode is especially relevant for founders, leaders, and anyone working under uncertainty who wants to turn mistakes into insight instead of regret.

Why do New Year’s resolutions fail so predictably—and what does that teach us about change at work? In this Mistake of the Week, Mark Graban explores why treating change as a test of willpower is a reliable setup for frustration, both personally and in organizations.

Drawing on behavioral psychology and leadership examples, the episode connects failed personal resolutions to common organizational mistakes: big announcements, ambitious targets, and too little attention to system design and psychological safety.

The takeaway is practical and actionable: instead of trying to boost motivation or eliminate human error, leaders should focus on making the right choices easier and the wrong ones harder—starting small, iterating, and learning forward instead of blaming backward.

Nick Saban calls it “the dumbest decision I ever made” — a fourth-and-one call from the 2001 SEC Championship Game that still sticks with him.

In this episode, Mark Graban breaks down why even the greatest coaches make mistakes, what Saban learned from the moment, and how leaders can turn high-pressure missteps into opportunities for trust and growth.

Perfect for listeners interested in leadership, football, coaching, and the psychology of mistakes.

Jingle Bells is one of the most recognizable Christmas songs ever written… except it wasn’t written for Christmas at all. In this week’s Mistake of the Week, we unpack one of America’s most enduring cultural misconceptions: the belief that Jingle Bells has anything to do with Christmas.

Originally titled One Horse Open Sleigh, the song debuted at a Thanksgiving church service in the 1850s and was inspired not by Santa or reindeer, but by noisy, fast sleigh races in Medford, Massachusetts. No Christmas trees. No North Pole. Just winter racing, youthful chaos, and a catchy melody.

Over the decades, repetition turned assumption into “truth,” and a Thanksgiving song quietly shifted into a holiday anthem. It’s a perfect example of how knowledge mistakes spread — harmless, familiar, and rarely examined.

In this 3–4 minute episode, Mark explains:

• Why Jingle Bells was never meant to be a Christmas song

• How repetition and cultural habit transformed it anyway

• What this teaches us about assumptions, organizational habits, and the stories we never question

• Why small knowledge mistakes can persist for generations

If you care about learning, improvement, and understanding how mistaken beliefs take root, this episode offers a fun seasonal reminder: even our most cherished “facts” deserve a second look.

In Episode #332 of My Favorite Mistake, Mark Graban talks with Dr. Josh McConkey — emergency physician, Air Force Reserve Commander, combat-deployed medevac leader, and Pulitzer Prize–nominated author. Known as the “MacGyver Doc,” Josh has spent his career solving problems in high-pressure environments where you rarely get a second chance.

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Josh shares the most painful mistake of his professional life: entering a business partnership without doing the proper due diligence. What followed was a cascade of red flags — Medicare violations, skimming, financial misconduct, and even a $3.4 million bribe offer he refused. The ordeal ultimately cost him nearly $5 million and forced him to rebuild his career and life with integrity front and center.

In our discussion, Josh explains how this experience reshaped his understanding of leadership, accountability, and courage — especially in systems where incentives can push good people toward dangerous choices. He also reflects on two decades in emergency medicine, including the structural failures that helped fuel the opioid crisis and the pressures physicians faced to prescribe narcotics.

Josh shares why he wrote Be the Weight Behind the Spear and his new children’s leadership book The Heart of a Leader, and why he believes character development must start far earlier than most of us realize. We close with his decision to run for Lieutenant Governor of North Carolina in 2028 — a move grounded in service, accountability, and a desire to strengthen public leadership.

This episode explores integrity, systemic failure, resilience, and the lessons we carry forward after a mistake that changes everything.

A 32-year-old woman in Switzerland underwent an unnecessary surgery after her lab sample was mixed up at Basel University Hospital. Doctors believed she had cervical cancer. She didn’t — but the procedure went ahead anyway, potentially affecting her ability to carry a pregnancy in the future.

In this Mistake of the Week, Mark Graban unpacks how such devastating but preventable errors happen — and why “being careful” isn’t a real safeguard. Drawing on past lab mix-ups he’s written about, Mark explores how system design, workload pressure, and weak error-proofing make these tragedies almost inevitable.

This isn’t about bad people or careless workers. It’s about fragile systems — and how hospitals can build processes that catch mistakes before they reach the patient. Because real safety starts with learning, not blaming.

My guest for Episode #331 of My Favorite Mistake is Andy Regal, a longtime media executive whose career has included leadership roles at The Wall Street Journal, MSNBC, Consumer Reports, Court TV, and CBS College Sports. He is also the author of the forthcoming book, “Surviving Bully Culture: A Career Spent Navigating Workplace Bullying and a Guide for Healing.”

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Andy shares a remarkable early-career mistake from his time producing NBC News war coverage with Lester Holt. A young staffer accidentally loaded last week’s script into the teleprompter, and Holt began reading it live on air. Andy, brand new to this type of broadcast, immediately assumed he’d face humiliation or even get fired. Instead, Holt responded with total calm, poise, and kindness—transforming what could have been a career-ending disaster into a lasting lesson on leadership.

That moment stands in sharp contrast to the bully bosses Andy encountered throughout his media career. We talk about how bullying shows up in subtle and overt ways, why high performers are often targeted, and how toxic leadership harms morale, performance, and even physical and mental health. Andy explains what recovery looks like and why his book is dedicated to helping people cope with, heal from, and navigate workplaces where bullying is tolerated or ignored.

• The wrong-script live TV moment with Lester Holt • Why calm leadership builds psychological safety • The emotional impact of bully bosses • Why bullying thrives in high-pressure environments • How bullying follows people home and affects well-being • What recovery looks like for targets of workplace bullying • Why Andy wrote Surviving Bully Culture

Andy Regal’s website & book pre-order: https://www.andyregal.com

In this Mistake of the Week, Mark Graban breaks down an incident involving an American Airlines A319 on final approach to Phoenix — captured on video with its landing gear still up. A cockpit alert sounded, the crew realized what was missing, and the pilots executed a safe go-around. Their explanation to air traffic control? A perfectly understated: “It wasn’t configured in the appropriate manner.”

Mark explores why these near-misses are less about individual oversight and more about systems built to detect — and correct — human error. From checklists to cockpit warnings to the decision to go around instead of pushing forward, this episode highlights why safety depends on catching mistakes early, not pretending they don't happen.