My Favorite Mistake: Business Lessons from Failures and Success

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: How lessons from Nebraska football and martial arts shaped Trevor’s resilience What Lean Six Sigma taught him about efficiency, quality, and leadership Why he focused on psychological safety and belonging to keep his team intact How he used outsourcing and automation to scale without burnout The importance of setting trajectories instead of rigid goals in business and life 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: What’s your favorite mistake? How did joining a multi-level marketing company at 19 shape your growth, even if it wasn’t financially successful? Did you ever think about leaving earlier, and was staying too long its own mistake? What lessons did you take from Nebraska football and sports about resilience and bouncing back? How did you first get into Lean Six Sigma and continuous improvement work? In what ways did Lean and coding skills help you scale your real estate business? What did you learn about leadership from running a 26-agent team with zero turnover? How did you create a culture of psychological safety and belonging for your team? Why do you emphasize inspiring people instead of “beating them over the head with metrics”? What role have outsourcing and automation played in your business success? You’ve said you set trajectories instead of rigid goals — what does that mean in practice? Looking back, how do you connect these mistakes and lessons to your current focus on investing, advising, and teaching?

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: What’s your favorite mistake? Was the mistake choosing this builder, or not verifying inspections before closing? Why do you think you didn’t speak up more during the building process? How does this experience connect to psychological safety in healthcare? What have you learned about yourself from going through this? How do you put the house problems into perspective? Has the builder taken responsibility or apologized? What parallels do you see between this home-building experience and healthcare improvement? Why is it so hard for healthcare organizations to admit mistakes? What role does leadership play in creating safer systems? How do hobbies like glass fusing help you practice learning from mistakes? What do you mean by “the mistake you’re planning”? What gives you hope for improvement in healthcare, despite the challenges?

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: What’s your favorite mistake? How did your trip to Europe during your PhD studies change your career path? Did you consider moving to Europe to teach in that more relaxed environment? What countries did you visit on that trip? How did you go from teaching to starting a retail store and then leading a manufacturing company? Did yoga and meditation help you become a better leader? How did your personal stress experiences influence how you led the company? How have attitudes toward workplace stress changed since the 1990s? How do you make meditation and stress relief practical for corporate settings? How do companies usually find and bring you in for corporate sessions? What types of people attend your retreats, and what do they take away? How did you personally discover the benefits of a consistent yoga practice? How can yoga and meditation help with stress-related physical issues? What are the “five kleshas” in yoga philosophy? How do those concepts connect to ego, attachment, and fear? What is the “inner council” in your book, and how does it work? How did your interest in astrology begin? How can knowing your “council leader” help you in life and work? How did you balance the drive to finish your book with avoiding stress? What’s your advice for building habits like meditation or yoga into daily life?

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: What’s your favorite mistake? When did you realize that listening to others more than yourself had become a pattern? How did the loss of your first love influence your journey of self-awareness and healing? What led you to start writing again after being discouraged? What is creative nonfiction, and how does it differ from other forms of writing? Did working with an editor bring up old doubts, and how did you manage that feedback process? How does Buddhism shape your view on mistakes? Does that mindset help you approach writing mistakes differently? How do you balance detachment from mistakes with still caring about your work? What does “communicating like a Buddhist” mean in everyday life? Can you give examples where helpful vs. hurtful language is more subtle? What’s the difference between being nice and being kind? How does changing our communication style help reduce stress? What inspired your newest book, The Pause? What’s an example of a workplace situation where not pausing leads to regret? What should someone do if they need a pause but the other person won’t allow it? How can we calm ourselves in the moment to respond more intentionally? What does it mean to respond from an “empty place”? What breathing techniques do you recommend in tough conversations?

🎙️ 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 #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: What’s your favorite mistake? How did you go from playing baseball to becoming CEO of Learnit? What lessons did you take from your baseball career into business? Did you ever regret turning down the chance to play minor league baseball? Was anyone cautioning you against overexpanding Learnit? What did you learn from that experience as a young CEO? How did you apply those lessons during the 2008 recession? How has your leadership style evolved since then? What does “being a Learn It All” mean to you? What kind of people do you look to hire and why? How do you balance vulnerability and confidence as a leader? What did you learn about receiving feedback from your time in sports? How do you avoid letting one failure affect your next decision or meeting? What’s the difference between failure and a mistake? Can you share more about your Learn It All podcast and what you’ve gained from it?

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: Is branding more about how others see you—like a nickname—than what you say about yourself? What was your favorite mistake? How was hiding behind your logo hurting your business? How close were you to publishing your book under a pseudonym? Was your publisher encouraging you to publish under your real name? What do you now teach others about personal branding as a result of that mistake? Why do you think many women hesitate to talk about their accomplishments? How did red become such a key part of your brand? What are some early steps someone can take to build their personal brand if they’re nervous about putting themselves out there? What gave you more confidence to show up consistently? How did entering awards help you boost your visibility and credibility?

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: What’s your favorite mistake? What did you overlook from your Eagle Scout experience that later became valuable in business? What specific mistakes did you make in those early years of running the firm? How do you apply situational leadership in your law firm? Can you share an example of helping someone move through that “frustrated learner” phase? What lessons from Scouting translate to business leadership? Did you ever think growing the firm beyond a solo practice was a mistake? What do you mean by “preventing stupid”? Can you explain your framework for categorizing business vulnerabilities? How do you distinguish ignorance from stupidity in business? What are examples of ill-discipline you’ve seen in your firm? Have you created checklists to avoid repeating mistakes? What is the Strong Protected Business System? How does your business immune system tool work? What do you mean by circular systems in business? How do you think about culture as your firm grows? Have you managed to avoid hiring narcissistic or toxic attorneys? How often do you get to play with your band, Geriatric Steel? Are your original songs available on Spotify or anywhere online?

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: What’s your favorite mistake? Why do you see going to law school as a mistake? What was your career before law school? What inspired you to make law your second career? How did you come to the decision to leave your first law firm? What happened between your first and second law firms? Why did you choose to launch a virtual firm in 2011? How did others react to your decision to work virtually? What did you do differently the second time to avoid repeating mistakes? What does it mean to have a systems-driven law firm? How do you help lawyers stop being the bottleneck in their business? Can you share examples of systems you recommend, especially for marketing? How do you coach lawyers through the fear of hiring after a bad experience? What mindset shifts help women lawyers move past perfectionism and indecision? What led you to focus exclusively on coaching women law firm owners?