My Favorite Mistake: Business Lessons from Failures and Success

In this edition of Mistake of the Week, Mark Graban tells a story that didn’t appear in any safety report or headline — it happened on a pickleball court. Early in learning the sport, Mark found his old tennis instincts taking over, leading to a very incorrect serve and a moment of embarrassment. What followed was a small but meaningful lesson in feedback, psychological safety, and the challenge of unlearning deeply wired habits. Supportive coaching, timely correction, and a friendly playing environment turned an awkward mistake into a productive one. Mark reflects on why unlearning is often harder than learning, and how leaders can create conditions where people feel safe enough to improve.

In this week’s Mistake of the Week, Mark Graban tells the story of a Maine hospital system that accidentally mailed condolence letters to 531 very-much-alive patients. The cause? A computer glitch — and a few missing fail-safes. Mark explores what this bizarre mix-up reveals about system design, automation, and trust in healthcare. Beyond the absurd headline lies a familiar pattern: when we blame people instead of learning from process failures, we guarantee more mistakes. So what does “fully resolved” really mean? And what can leaders learn from a mistake that’s literally to die for? If you received this episode through your podcast app and not a séance, you’re doing fine.

We’re going back to Episode 30 from January 2021, featuring Katie Anderson — author of Learning to Lead, Leading to Learn — and Isao Yoshino, the longtime Toyota leader whose career and lessons inspired her book. Episode page with video, transcript, and more It was such a privilege to talk with them then, and even more meaningful now, because I recently got to spend time with Mr. Yoshino in Japan last October during Katie’s Learning to Lead, Leading to Learn experience. Seeing him there — humble, curious, and still passionate about developing others — really reinforced everything we talked about in that episode. Mr. Yoshino shared a story from early in his Toyota career, when a mistake on the shop floor could have led to punishment, but instead led to learning. His leaders didn’t blame him — they worked with him to fix the system. That experience shaped how he led and coached for decades. Katie shared her own favorite mistake — a story about feedback early in her career that helped her realize the power of listening, asking questions, and helping others find their own answers. Together, we explored what it means to create a culture where people feel safe to learn, improve, and grow — the kind of culture that turns mistakes into progress.

My guest for Episode #328 of the My Favorite Mistake podcast is Emily Aborn, a small business copywriter, speaker, and host of the Small Business Casual podcast. Episode page with video, transcript, and more Emily helps entrepreneurs bring clarity, creativity, and authenticity to their marketing. Before finding her true calling, she owned a brick-and-mortar organic mattress store—a business that looked great on paper but didn’t align with her passions or strengths. Emily shares how this “perfect-on-paper” business became her favorite mistake. Though the store was profitable, she found herself feeling trapped, unfulfilled, and disconnected from the work she truly loved. Through closing that chapter, Emily discovered what she actually enjoyed most—writing, connection, and storytelling—and turned those insights into a business built around her natural skills. Today, Emily works with entrepreneurs across industries to find their authentic voice and create meaningful marketing. In this episode, she and Mark explore lessons about self-awareness, alignment, and how mistakes can guide us toward a more fulfilling path. Emily also shares practical insights on copywriting, understanding your audience, and why genuine collaboration beats fear-based marketing every time. Questions and Topics:

My guest for Episode #327 of the My Favorite Mistake podcast is Dr. Maya Ackerman, AI pioneer, researcher, and CEO of WaveAI. She’s also an associate professor of Computer Science and Engineering at Santa Clara University and the author of the new book Creative Machines: AI, Art, and Us. EPISODE PAGE WITH VIDEO, TRANSCRIPT, AND MORE In this episode, Maya shares her favorite mistake — one that changed how she builds technology and thinks about creativity. Early in her journey as an entrepreneur, her team at WaveAI created an ambitious product called “Alicia,” designed to assist with every step of music creation. But in trying to help too much, they accidentally took freedom away from users. That experience inspired her concept of “humble AI” — systems that step back, listen, and support human creativity rather than take over. Maya describes how that lesson led to their breakthrough success with Lyric Studio, an AI songwriting tool that empowers millions of artists by helping them create while staying true to their own voices. She also shares insights from her research on human-centered design, the philosophy behind generative models, and why we should build AI that’s more collaborative than competitive. Together, we discuss why mistakes — whether made by people or machines — can spark innovation, and how being more forgiving toward imperfection can help both leaders and creators thrive. “If AI is meant to be human-centric, it must be humble. Its job is to elevate people, not replace them.” — Maya Ackerman “Who decided machines have to be perfect? It’s a ridiculous expectation — and a limiting one.” — Maya Ackerman Questions and Topics: Lyric Studio

My guest for Episode #326 of the My Favorite Mistake podcast is Dr. William Harvey, a manufacturing executive and university professor whose career is defined by developing people, strengthening systems, and driving organizational excellence. A proud U.S. Marine, William carries forward a deep tradition of service and leadership. He also serves as the chair for the 2026 AME International Conference in Milwaukee, hosted by the Association for Manufacturing Excellence (AME). EPISODE PAGE WITH VIDEO AND MORE William shares a powerful early-career story about a mistake that taught him lasting lessons about trust, humility, and psychological safety. When he accidentally derailed a customer order by taking home the wrong document, he feared the worst. Instead, his manager’s calm and compassionate response—and a customer’s extraordinary effort to make things right—changed how William thought about leadership forever. Over time, William applied those lessons to how he leads teams and builds culture. He believes that leaders go first—by admitting mistakes, showing vulnerability, and creating space for others to experiment, fail, and learn. Through daily coaching cycles and methods like Toyota Kata, he helps people develop confidence in problem solving and take ownership of improvement. His goal: to build a workplace culture rooted in trust, respect, and continuous learning, where every person feels safe enough to speak up and strong enough to lead. Key Lessons & Themes:

In this bonus re-release, we revisit an important and timely conversation with Sabrina Moon, Founder and CEO of The Problem Solving Institute and a certified Dare to Lead™ facilitator. Originally aired as Episode #35 of My Favorite Mistake, this conversation remains one of the most powerful and honest reflections on leadership, shame, and transformation. Episode page with transcript and more 🔍 What You’ll Hear: Sabrina’s “favorite mistake” — using shame as a leadership tool in high-stress environments The culture of command-and-control leadership she inherited (and how she broke the cycle) How Brené Brown’s work on vulnerability and shame helped her lead differently The personal toll of shame-based leadership — on her team and herself Why self-awareness is a skill—and how we can build it The role of grace, compassion, and curiosity in becoming a better leader “We use shame and the fear of shame to motivate, but I think in an unhealthy way. I would utilize shame because it was the last tool in my toolbox and I was desperate.” — Sabrina Moon 👤 About Sabrina Moon: Sabrina is a leadership coach and consultant who helps organizations move from reactive command-and-control cultures to psychologically safe environments where continuous improvement and innovation can thrive. Connect with her at ProblemSI.com or on LinkedIn. ✨ Why Re-Release This Episode? As more organizations reflect on how culture impacts performance, engagement, and well-being, this episode offers essential insights for leaders at every level. Whether you're managing a team or transforming a system, Sabrina's story reminds us that who we are as leaders matters just as much as what we do.

My guest for Episode #325 of the My Favorite Mistake podcast is Phillip Cantrell, EVP of Strategy at United Real Estate, founder of Benchmark Realty, and author of Failing My Way to Success: Lessons from 42 Years of Winning and Losing in Business. EPISODE PAGE WITH VIDEO, TRANSCRIPT, AND MORE Phillip reflects on more than four decades of entrepreneurial ups and downs across printing, real estate, and related ventures. He openly shares how devastating mistakes—including putting “all his eggs in one basket”—forced him to reinvent his approach. What looked like a catastrophe in 2007–2008 became the turning point that fueled Benchmark Realty’s rapid growth to nearly 2,000 agents. “Failure is going to happen. If you don’t make mistakes, you’re not doing anything.” In this conversation, Phillip and I talk about the difference between scaling vs. scrambling, the dangers of playing “not to lose” instead of “playing to win,” and why documenting processes is essential for growth. He also explains why your only real competitor is “the man in the mirror” and how daily reflection helps him learn from mistakes and avoid repeating them. This episode is packed with timeless lessons on leadership, resilience, and learning from failure—whether you’re in real estate or any other industry. “If you play not to lose in business, you’re already losing.” Questions and Topics:

In this very special solo episode of My Favorite Mistake, Mark Graban breaks down the gloriously ridiculous — and surprisingly instructive — mistakes made by the characters in his all-time favorite film, This Is Spinal Tap. With the long-awaited sequel, Spinal Tap II: The End Continues, now in theaters, Mark shares stories from attending the IMAX premiere in Los Angeles, including a post-film Q&A with Rob Reiner, Michael McKean, Christopher Guest, and Harry Shearer. Mark explores why Spinal Tap endures not just as a cult comedy classic, but as a brilliant satire of human behavior, team dysfunction, communication breakdowns, and leadership gone sideways. And yes — these mistakes still matter, even four decades later. From the Stonehenge measured in inches… To the foil-wrapped “courgette” in the pants… To the pod that wouldn’t open and the drummers who keep dying… …these moments are funny because they’re true. And they’re great reminders that how we respond to mistakes matters more than pretending they never happened. 🔑 Topics & Highlights: Why This Is Spinal Tap is more than just a comedy The iconic “Stonehenge” prop mistake and what it teaches us about communication How real-life rockstars refused to drum in the sequel (because of the “curse”) Why remembering the courgette as a cucumber is itself… a mistake The brilliance of “We don’t have time for that” and the backstage loop in Cleveland Why doing what you’re told isn’t the same as doing what’s right Mark’s personal story of seeing the film 100+ times — starting with a VHS in high school 🔗 Mentions & Links: 🎬 This Is Spinal Tap on IMDb 🎥 Spinal Tap II: The End Continues – Now in Theaters 📘 The Mistakes That Make Us by Mark Graban 💻 SpinalTarp.com – A curated list of character mistakes from the film 🎧 Subscribe & Follow: If you enjoyed this episode, make sure to subscribe, leave a review, and check out past episodes of My Favorite Mistake — where we talk to leaders, authors, entrepreneurs, and creatives about the mistakes that made them who they are. 🎙️ Listen on Apple Podcasts, Spotify, or wherever you get your shows.

My guest for Episode #324 of the My Favorite Mistake podcast is Trevor Schade. Episode page with video, transcript, and more Trevor began his career as a Lean Six Sigma Black Belt with a strong background in coding and process improvement. He consulted on business efficiency and outsourcing before shifting into real estate in 2008. After earning his license, he quickly built a top-performing team of 26 agents with zero turnover over five years. By leveraging a virtual admin team in the Philippines and innovative automation, Trevor’s group generated over a million dollars in commissions. In late 2023, Trevor stepped away from leading that large team to focus on investing, advising, and teaching. Today, he speaks on topics including negotiation, time freedom, and real estate strategy, and he has launched Life Wealth courses to help others pursue similar goals. In this episode, Trevor shares his favorite mistake: jumping into a multi-level marketing business at age 19. The venture wasn’t financially successful, but it transformed his mindset. For the first time, Trevor developed a daily reading habit that exposed him to classics like Dale Carnegie’s How to Win Friends and Influence People and Robert Kiyosaki’s Rich Dad, Poor Dad. Those books gave him a foundation in psychology, leadership, and long-term thinking that continues to influence his work. We also explore: Trevor’s story is a reminder that sometimes the most unprofitable ventures provide the richest education — if we’re willing to learn from them. Questions and Topics:

In this special episode of My Favorite Mistake, host Mark Graban celebrates the kickoff of football season with a unique perspective: five legendary kickers who know what it means to perform under pressure. Guests include former NFL kickers Jay Feely, Shane Graham, David Akers, Nick Lowry, and University of South Carolina’s all-time leading scorer Parker White. These athletes share their most memorable mistakes and high-pressure moments—from Jay Feely’s infamous game-losing kicks and Saturday Night Live parody, to Shane Graham’s insight that failure and success are inseparable, to Nick Lowry’s persistence after 11 rejections before making the NFL. David Akers reflects on striving for improvement over perfection, while Parker White explains how practice and faith helped him overcome nerves and pass lessons on to the next generation. Across their stories, a common theme emerges: mistakes don’t define you—they prepare you. By reframing failure, focusing on fundamentals, and staying mentally strong, these kickers transformed pressure into performance. Their lessons reach far beyond football, offering wisdom for leaders, teams, and anyone facing high-stakes challenges in business or life. If you’ve ever struggled with fear of failure, performance anxiety, or the pressure to succeed, this episode offers practical, inspiring insights from athletes who’ve been tested in front of millions.

My guest for Episode #323 of the My Favorite Mistake podcast is Grace Bourke, Consulting Director of the Performance Excellence Practice at Baker Tilly. With nearly 40 years of experience in healthcare quality improvement and industrial engineering, Grace has worked in clinical care, biotech, global public health, and senior leadership roles at organizations including Kaiser Permanente and Sutter Health.' Episode page Grace shares a very personal favorite mistake — the challenges of building a new home that turned into a nightmare of mold, leaks, and structural flaws. What began as a house problem quickly became a more profound lesson in trust, verification, and speaking up — themes that resonate far beyond construction and directly into the world of healthcare. “Trust and verify becomes trust and vigilant, educated verification.” – Grace Bourke She reflects on how her tendency to trust inspections and processes, while ignoring her own instincts, parallels what often happens in healthcare systems when leaders or staff don’t feel psychologically safe to raise concerns. Grace connects her experience to the importance of leadership accountability, patient safety, and continuous improvement, noting that healthcare still struggles to admit mistakes and act decisively to prevent harm. We also talk about the role of psychological safety, second opinions, and lifelong learning, both in our personal lives and in healthcare. Grace shares how hobbies like glass fusing remind her that safe spaces for experimentation and “planned mistakes” can strengthen resilience, creativity, and growth. “We can’t fix the whole world, but we can fix our small piece — and that makes a difference.” – Grace Bourke Questions and Topics:

My guest for Episode #322 of the My Favorite Mistake podcast is Rob Dorgan, a multi-talented professional whose career path has taken him from paralegal to college professor, retail store owner, manufacturing company president, and now licensed massage therapist, certified yoga educator, meditation teacher, and astrologer. Rob is also the author of Awakening the Mystic: A Novel of Cosmic Love and Healing. Episode page with video and more His favorite mistake? Taking what was meant to be a short trip to Europe while working on his PhD — a journey that led him to never return to that academic track. Instead, it opened his eyes to a different pace of life, sparked a reassessment of what success meant to him, and ultimately set him on a more balanced and meaningful career path. In our conversation, Rob shares how that decision — which family and friends initially questioned — allowed him to escape burnout and embrace a life and career that integrates his passions for teaching, creativity, and well-being. He reflects on lessons learned from his “type A” years in academia and business, the importance of slowing down, and how yoga, meditation, and practical stress relief can improve both personal health and workplace culture. We also discuss his experience bringing these tools into corporate environments, where employees not only benefit individually but also feel more supported by their organizations. “Stress comes on so slowly that it becomes your normal — and you forget what life without it feels like.” That realization, Rob says, is what helped him see the deeper value of meditation and mindful living. We also talk about his book’s concepts — from the “five kleshas” in yoga philosophy to the idea of an “inner council” — and how self-awareness can help us navigate life’s choices. Whether you’re navigating a career change, seeking better work-life balance, or simply curious about practical ways to reduce stress, Rob’s story offers valuable insights and inspiration. Questions and Topics:

My guest for Episode #321 of the My Favorite Mistake podcast is Cynthia Kane, founder and CEO of the Kane Intentional Communication Institute and author of several books, including How to Communicate Like a Buddhist and The Pause: How to Keep Your Cool in Tough Situations. Cynthia shares a pivotal mistake from early in her life: letting other people’s opinions matter more than her own—especially after a college professor told her she’d never be a good writer. That moment stung, but it also eventually propelled her toward a path of mindfulness, self-trust, and transformational communication. Cynthia explains how her journey through loss, meditation, and Buddhist principles helped her develop a more intentional way of communicating—not just with others, but with herself. We explore how mistakes, reactivity, and emotional attachment can all be reframed through mindfulness and self-awareness. Cynthia offers practical tools for staying calm during high-stakes conversations, including pausing, resetting the nervous system, and learning to speak from an “empty place”—a state of clarity without judgment or reactivity. “Every mistake leads us to something better.” Throughout the conversation, we also unpack the difference between being nice and being kind, how communication impacts stress levels, and why helpful language is honest, kind, and necessary. Cynthia’s insights are especially valuable for leaders, teams, and anyone who wants to communicate more effectively under pressure. As she says, “Every mistake leads us to something better.” Questions and Topics:

🎙️ In this bonus episode of My Favorite Mistake, Mark Graban welcomes back Dr. Jen Heemstra, Charles Allen Thomas Professor and Chair of Chemistry at Washington University in St. Louis. Jen joins us to talk about her new book, Lab Work to Leadership: A Concise Guide to Thriving in the Science Job You Weren’t Trained For. She shares how the book was inspired by her favorite mistake—realizing that a research career in science unexpectedly came with a leadership role she wasn’t trained for. What began as a personal challenge turned into a passion for mentorship and a practical guide to help others in the sciences (and beyond) succeed as “accidental leaders.” 👉 Learn how Jen approached this transition, what others in academia and technical fields can take away, and why leadership training is essential—even if it’s not part of your job description (yet). 🧪 “People are counting on you to get this leadership thing right.” – Jen Heemstra 🔁 Listen to Jen’s original episode (#262) where she shares her favorite mistake: http://markgraban.com/mistake262 🎧 Listen to all episodes at https://www.markgraban.com/mistake

My guest for Episode #319 of the My Favorite Mistake podcast is Sapna Pieroux, award-winning author of Let’s Get Visible!, a branding consultant, and the founder of Inner Visions ID. Episode page with video, transcript, and more With a background spanning 20 years in media and experience working with major brands like Toyota, Sony, and L’Oréal, Sapna shares the defining mistake that led her to a new level of impact: believing that her great work alone would speak for itself. Early in her entrepreneurial journey, she hid behind a company logo and resisted putting herself out there—fearing criticism, judgment, and even considering a pseudonym for her book. In this honest and inspiring conversation, Sapna shares how she overcame those fears and the societal pressures—especially those that affect women and people of color—to stay small or silent. Through her own evolution, she discovered the power of personal branding and visibility, not just for business growth but for personal confidence. She now helps leaders and teams align their business and personal brands so they can show up with clarity, confidence, and credibility in a noisy world. We also explore common branding mistakes—like trying to DIY logos without strategy—and how Sapna’s signature “Do-Say-See” model helps entrepreneurs and professionals build trust and influence. Whether you're just starting out or trying to get unstuck, Sapna’s insights on visibility, imposter syndrome, and brand alignment will give you practical tools and thoughtful encouragement. Questions and Topics:

My guest for Episode #318 of the My Favorite Mistake podcast is Matthew Neal Davis, an attorney, entrepreneur, and author of the provocative book The Art of Preventing Stupid. Episode page with video and more Matthew is the founder and managing partner of Davis Business Law, which has grown more than 1,000% in six years, earning a spot on the Inc. 5000 list. In addition to running a multi-office law firm across several states, he’s also the frontman of a heavy metal band called Geriatric Steel. In this episode, Matthew shares how not fully recognizing the leadership lessons from his Eagle Scout experience early in his legal career became a favorite mistake—and how it shaped the way he leads his firm today. Matthew reflects on the hiring and leadership missteps that stemmed from overlooking those early lessons—particularly how applying Ken Blanchard’s Situational Leadership framework helped him better support team members through growth phases. He explains how understanding where someone is on the spectrum from “excited beginner” to “self-reliant high achiever” has transformed how he mentors attorneys and minimizes costly turnover. These insights, combined with structured systems and data dashboards, now fuel a high-performance culture rooted in learning and ownership. ...we have rituals around this. Every Wednesday is WINSday—we celebrate successes. Every Friday, we have a firm huddle where we talk about what kicked our butts that week. We put it all on the table. That’s how we learn. That’s how we build trust and improvement into the culture. We also talk about the core idea behind Matthew’s book: that most business problems come from one of three vulnerabilities—catastrophes, ignorance, or ill-discipline—and how leaders can build a "business immune system" to prevent them. From mismanaged Google Ads campaigns to ill-advised partnerships, Matthew brings humor and clarity to how we can all learn faster, prepare better, and focus on growth. His story is a compelling reminder that being proactive beats being reactive—and that embracing mistakes is the best way to strengthen your systems and your culture. Questions and Topics: Strong Protected Business System

My guest for Episode #320 of the My Favorite Mistake podcast is Damon Lembi, CEO of Learnit, a live learning and development platform that has helped upskill over 2 million professionals. Episode page with video, transcript, and more A former college baseball player and now a two-time bestselling author, Damon shares the story of how youthful ambition and overconfidence led him to push Learnit into a rapid, unsustainable expansion during the dot-com boom. Despite his father’s cautious advice, Damon got his way—and then faced the harsh reality of a collapsing market and near bankruptcy. In our conversation, Damon reflects on the hard-earned lessons from that pivotal mistake, including the dangers of comparing yourself to others, the importance of thinking through worst-case scenarios (what he now calls “purposeful awfulizing”), and the humility required to be a “Learn It All” leader. His resilience and willingness to grow through adversity helped him guide Learnit not only through the early 2000s tech crash, but also through the 2008 recession and beyond. “If you’re always right, you’re not listening hard enough.” Damon shares how his background as a competitive athlete shaped his mindset around failure, feedback, and agility—traits that now inform how he builds his team and company culture. We also talk about his podcast, The Learn It All Podcast, where he continues learning from top authors, leaders, and changemakers. Damon’s story is a powerful reminder that mistakes can be an expensive—but invaluable—education. “Make new mistakes, learn from them, and move forward.” Questions and Topics:

My guest for Episode #316 of the My Favorite Mistake podcast is Davina Frederick, founder of Wealthy Woman Lawyer, host of the Wealthy Woman Lawyer Podcast, and a business coach who has helped women law firm owners scale their practices to seven figures and beyond. Episode page with video, transcript, and more In our conversation, Davina shares why going to law school—an unconventional move at age 38—turned out to be her favorite mistake. Despite building a successful litigation practice, she realized that the traditional lawyer lifestyle wasn’t aligned with her long-term goals or well-being. "I realized I didn’t want to spend the rest of my life sitting behind a desk or in a courtroom." After stepping away from her first firm, Davina leveraged both her marketing background and the painful lessons of burnout to build a second, more sustainable law practice. That experience—and the power of hiring business coaches—ultimately led her to launch her own coaching firm. Today, Davina specializes in helping women lawyers grow their firms with clarity, confidence, and systems that reduce overwhelm and create balance. We also dive into what it means to create a systems-driven law firm—and how that principle applies across professional services. From breaking the “grading papers” bottleneck to resisting perfectionism, Davina offers practical strategies for founders who are ready to scale without losing themselves in the process. Her journey is a powerful example of learning from mistakes, listening to your inner voice, and having the courage to change course. Questions and Topics:

My guest for Episode #316 of the My Favorite Mistake podcast is Jim Schleckser, founder and CEO of The CEO Project. Episode page with video, transcript, and more Jim is a seasoned business leader, bestselling author, and trusted advisor to CEOs around the world. With experience spanning 42 countries and multiple industries, Jim has spent decades helping leaders grow their companies and think more strategically. He’s also the author of Great CEOs Are Lazy and Professional Drinking, and he’s a certified sommelier—something we get to at the end of the episode! In our conversation, Jim shares a formative early-career mistake—being too optimistic as a leader. His enthusiasm led to overpromising revenue, under-delivering on results, and ultimately damaging his credibility to the point where he had to leave the organization. Jim reflects on how he’s since learned to balance positivity with realism, buffer commitments, and truly listen to skeptics on his team. His story is a powerful reminder that leadership isn’t just about vision—it’s also about judgment, humility, and learning from painful experiences. We also dive into what it means to be an effective CEO, including why Jim says great CEOs are lazy. He shares how high-performing executives focus their time on removing bottlenecks, not micromanaging, and why a trusted CEO peer group can be a game-changing support system. Plus, for fellow wine lovers, we cap off the episode with a fun bonus: wine mistakes, how to order like a pro, and Jim’s best tip for getting the most out of a wine list. Questions and Topics: