My Favorite Mistake: Business Lessons from Failures and Success

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?

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: What’s your favorite mistake, and what did you learn from it? Can you share specific examples of how your optimism led to overcommitment or missed expectations? How did that mistake affect your credibility and position in the company? How have you learned to balance optimism with realism in leadership? What’s your approach to setting stretch goals versus achievable targets? How can unrealistic goals create dysfunction or unethical behavior in organizations? What’s the best way to avoid data manipulation and maintain integrity in performance reporting? What is The CEO Project, and how does a CEO peer group provide value to its members? You say “great CEOs are lazy”—what does that really mean, and how does it work in practice? How can CEOs identify the biggest constraint or bottleneck in their business? Why do some CEOs struggle to admit mistakes, and how does that affect their leadership credibility? How do peer groups foster psychological safety for leaders? What inspired you to become a certified sommelier? What are some common mistakes people make when ordering wine? What’s your best tip for confidently ordering wine at a restaurant? If someone only drinks Napa Cabernets, what’s a good way to branch out? Have you observed gender bias in how sommeliers treat guests at the table?

My guest for Episode #315 of the My Favorite Mistake podcast is Kat Halushka, a business and visibility strategist for coaches, consultants, and speakers. She’s the founder of Profitable Impact Academy, where she helps entrepreneurs grow their audience, automate marketing, and land clients through speaking and streamlined funnels. EPISODE PAGE Kat’s favorite mistake? She followed the classic advice to “go to networking events and have coffee meetings” to get clients—so she did, hundreds of times. But after exhausting herself with back-to-back coffee chats every Friday, she realized the ROI just wasn’t there. Kat had a breakthrough when she nervously gave a short talk at a networking event—and walked away with two new clients that day. That lightbulb moment launched her on a mission to get in front of the room instead of meeting people one-on-one. Over time, she built her credibility by hosting her own events, attracting hundreds of attendees and growing a thriving business community. This shift helped her discover that strategic speaking, not endless small talk, was the true key to visibility and client conversion. Today, Kat teaches entrepreneurs to stop chasing every opportunity and instead focus on clarity, messaging, and scalable systems. She shares powerful lessons on why most new speakers fail to connect—and how you can avoid those pitfalls by making offers that speak to your audience’s present-day pain points. Whether you’re brand-new to business or looking to scale with less hustle, Kat’s insights on visibility, messaging, and mistake-making will help light the way forward. Questions and Topics: What’s your favorite mistake? How did those endless coffee meetings affect you and your business? What changed after that first speaking engagement? How did you start landing more speaking opportunities after that breakthrough? What was the origin story behind Profitable Impact Academy? What are some of the most common mistakes entrepreneurs make when trying to grow through speaking? How can business owners get clearer on what their audience really needs? Why is it a mistake to create too many offers or talks? How do you help clients identify and refine the one talk that drives results? What are the differences between speaking as a business vs. speaking to grow a business? When offered a speaking fee, how do you decide whether to accept or negotiate for something else? Can you explain what you mean by making an “offer from the stage”? How do you structure a win-win-win when working with event organizers? What’s one way speakers can make a compelling call-to-action without sounding salesy? Can you give an example of a “gift” that actually gets audience engagement? What’s your final advice for new entrepreneurs or aspiring speakers?

In this special bonus episode of My Favorite Mistake, host Mark Graban welcomes back Josh Cunningham, founder and CEO of Rokrbox and guest from Episode 244. Josh returns to share insights from his brand-new book, Culture Is the Key: How to Unlock Massive Profits and Freedom. We dive into: How Josh built a culture-first company that’s thriving—even in a tough real estate market Why cutting costs doesn’t have to mean cutting people or quality The inspiration and process behind writing his book What it means to create a Five-Star Company Culture Josh also reflects on what he’s learned since his last visit, including the power of simplification, scaling with intention, and how purpose has driven Rockerbox's explosive growth. “Culture isn’t just a vibe—it’s the engine behind every result.” “We asked: What’s the least amount of work a person has to do to move the needle—and how can we reward them more for it?” 📕 Grab the book: Culture Is the Key is available now on Amazon and Barnes & Noble 🎧 Listen to Josh’s first episode: My Favorite Mistake #244 Subscribe for more stories about leadership, culture, learning from mistakes, and growth. 🔔 Don’t forget to like, comment, and share if this resonated with you! #CompanyCulture #Leadership #Entrepreneurship #SmallBusinessGrowth #JoshCunningham #Rockerbox #CultureIsTheKey #BusinessBooks #MarkGraban #MyFavoriteMistake #StartUpLife #FiveStarCulture #WorkplaceCulture #BusinessLeadership