Learning From Mistakes: Norman Wolfe’s Guide To Building High-Performing Teams My Favorite Mistake: Business Lessons From Failures And Success podcast

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My guest for Episode #313 of the My Favorite Mistake podcast is Amber Gaige , a marketing strategist, international bestselling author, and founder of Far Beyond Marketing . With over 20 years of experience, Amber helps entrepreneurs simplify their marketing and drive real results. She’s also the author of The Far Beyond Marketing Guidebook: Stop Being Duped by Bad Marketing , and the creator of the Four Cs of Effective Marketing Framework. In this episode, Amber shares her favorite mistake—spending more than a decade working in a large, multi-division family business. While the experience taught her resilience, leadership, and business fundamentals, she reflects on how staying too long delayed her ability to find her own voice and build something truly independent. She opens up about the emotional complexity of leaving, the pressure of navigating work and family, and how that leap led her to grow—and eventually sell—a marketing business that launched her next chapter. We also discuss common mistakes businesses make when it comes to marketing, especially when selecting agencies or falling for one-size-fits-all tactics. Amber highlights the importance of clear messaging, knowing your ideal customer, and embracing AI wisely—without letting it replace human insight. Her story is one of tenacity, self-discovery, and servant leadership—a valuable listen for any entrepreneur or leader navigating growth, branding, or family dynamics. Questions and Topics: What’s your favorite mistake from your career? What kind of family business were you involved in? Did you choose to join the business, or was it more of an expectation? Was your initial role in the family business something you wanted? Did it feel like a mistake right away, or did that come later? Were you involved in marketing within the family business, or did you have to leave to pursue that? Were your parents both in leadership roles? And were you held to a higher standard? What was the process like for deciding to leave the family business? How did the opportunity to build and spin off your own marketing company come about? Was selling the business to private equity your exit strategy from the family business? How did you apply lessons from the family business to your new venture? What challenges come with hiring or firing family members in a business? How did you transition from operating under the family umbrella to running your own company? What does "Far Beyond Marketing" mean to you and your clients? What does servant leadership mean in the context of your work? Do you have any stories of helping clients recover from marketing mistakes? What are some common mistakes businesses make when hiring a marketing agency? What are some newer marketing mistakes you're seeing, especially related to technology? What’s a smart way to use AI in marketing—and what’s a mistake to avoid? Can businesses be penalized for publishing AI-generated content? How can business owners use a book as a strategic tool beyond just sales? What are your Four Cs of effective marketing? How do you define “brand” beyond just a logo? Is it possible for marketing firms to unintentionally mislead clients?…

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TAKE TWO: Ballet, Mistakes, and Masked Performances: Jared Redick’s Story of Grace Under Pressure 42:44

10 days ago42:44

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OOPS! Due to an editing mistake, I had to reupload the file. Again. My guest for Episode #312 of the My Favorite Mistake podcast is Jared Redick , a third-generation ballet dancer, choreographer, and award-winning educator. Episode page with links and more Jared is a full professor and Assistant Dean of Dance at the University of North Carolina School of the Arts. He has performed with renowned companies including the Boston Ballet and Miami City Ballet, and now shapes the next generation of dancers through his leadership, coaching, and innovation in arts education. In our conversation, Jared shares his favorite mistake—one that unfolded during the height of the COVID-19 pandemic while producing a filmed version of The Nutcracker . A critical planning misstep nearly derailed the production when sets weren’t ready for a pivotal weekend of shooting. Facing immense time pressure and logistical complexity, Jared and his team were able to regroup, adapt the schedule, and ultimately find a better way forward. The experience became a lesson in flexibility, communication, and leading with calm under pressure. Jared also reflects on his transition from performer to educator, how he defines effective leadership, and what it means to embrace vulnerability in pursuit of growth. We explore how his equity-focused curriculum changes are reshaping the world of ballet and how earning an MBA is helping him integrate business thinking into the arts. Throughout the episode, Jared’s humility, clarity, and passion for mentorship shine through. Questions and Topics: What’s your favorite mistake, and what happened during the COVID-era Nutcracker production? How did you lead your team through the anxiety of that situation and find a solution? Was the missed set deadline more of a communication issue or a planning breakdown? Were there lasting lessons from that project that apply to future productions? Was anyone blamed or punished for the mistake—or was it handled differently? What role does leadership play in preventing or responding to these types of issues? What stage of the pandemic were you in when filming The Nutcracker ? Were dancers masked? Can you tell us more about your personal path into dance and your early training? How does the transition from high school conservatory to professional ballet typically work? How did you navigate your own transition from performing to teaching and leadership? As a performer, how did you deal with the possibility—or reality—of making mistakes on stage? How do performers balance self-assessment with celebrating what went well? Did you regularly receive feedback or review recordings of your performances? How has your leadership style evolved as an assistant dean and teacher? What are “equity-focused curriculum updates,” and how are they changing ballet education? What are some challenges in making ballet more inclusive and accessible? How does bias in dance differ from other performing arts like music? What has been most eye-opening in your MBA program coming from an arts background? How do business tools like project management software support the arts? What does “embracing vulnerability” mean to you, and how does it relate to learning from mistakes?…

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How a Mistake in Confronting Workplace Discrimination Shaped a Leadership Career – Karin Hurt on Speaking Up the Right Way 40:51

17 days ago40:51

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My guest for Episode #311 of the My Favorite Mistake podcast is Karin Hurt , CEO of Let’s Grow Leaders , a global leadership development firm. Karin is a former Verizon Wireless executive and the award-winning author of five books, including her latest, Powerful Phrases for Dealing with Workplace Conflict . Episode page with video, transcript, and more In this episode, she shares a deeply personal and professionally pivotal story from her corporate days—an impassioned confrontation over a discriminatory hiring decision that, while well-intentioned, caused serious damage to her career. Karin unpacks how her emotional reaction—rooted in a strong sense of justice—ultimately undermined her goal. Despite advocating successfully for her team member, her public and heated delivery hurt her leadership reputation. She reflects on the importance of staying calm under pressure, choosing the right time and place to speak up, and communicating with both courage and strategy. These lessons became the foundation for the work she does today, helping leaders navigate difficult conversations with confidence and compassion. Throughout the episode, we also discuss her transition from corporate executive to keynote speaker, author, and entrepreneur. Karin explains how she and her co-author (and husband), David Dye, help teams build cultures of “productive conflict,” where differences lead to innovation rather than division. From real-world mistakes to powerful communication tools, this episode is full of insight for leaders who want to lead with heart—and get results. Questions and Topics: What’s your favorite mistake, and what did you learn from it? Do you think the hiring manager eventually saw the light, or was the outcome driven by HR? Did that incident influence your decision to leave the corporate world and start your own company? How did your background in HR and operations shape your leadership approach? When did you realize you had something valuable to share publicly through your blog? How did your speaking career take off, and what was the turning point? How do you stay calm in conflict now, compared to earlier in your career? What are the four dimensions of productive conflict? How often do leaders get in trouble for what they say versus staying silent? How do you advise someone to say “no” to their boss without hurting their reputation? What are the dynamics of working with your husband as a business partner? How can teams embrace conflict as a source of innovation, not dysfunction? What’s the danger of trying to fix systemic conflict at the interpersonal level? How do you handle conflict on hybrid or global teams where trust is harder to build? Is it easier to de-escalate conflict in person versus virtual or text-based communication? How do you balance encouraging courage with creating psychological safety?…

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What Nearly Killed Andrew Laws’ Business—and Why He’s Now Grateful for It 41:48

23 days ago41:48

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My guest for Episode #310 of the My Favorite Mistake podcast is Andrew Laws , Founder of the SEO agency Yeseo IO and host of The Business Amplifier Podcast . Andrew has been working in digital marketing for over 25 years and has seen just about every shift in the SEO landscape. But one of the biggest lessons of his career came not from Google’s algorithm, but from a catastrophic business event involving hackers, a two-year police investigation, and a decision that changed everything. Episode page Andrew shares the harrowing story of building a successful web hosting company—only to have it destroyed by cybercriminals just as he was preparing to sell it. The hackers didn’t just crash servers—they triggered legal threats, emotional exhaustion, and a complete shutdown of Andrew’s businesses at the time. But through that painful chapter, Andrew found clarity. He realized he had been doing too much alone and needed to build smarter, more resilient systems—and a team he could trust. In our conversation, Andrew talks candidly about burnout, delegation, and how the right mistake can become a turning point. He also shares practical insights into what SEO really is (and isn’t) in 2025, why many people misunderstand Google’s algorithms, and why "doing good stuff" consistently still beats gimmicks and shortcuts. Whether you're a business owner, marketer, or just someone who's ever felt overwhelmed, Andrew’s story offers a timely reminder: the hardest setbacks can lead to the most meaningful resets. Questions and Topics: What’s your favorite mistake ? How did the hackers get in, and what did the police uncover? Why did you shut down not just the hosting business but also your SEO company? Did the hackers have a clear motive—was it ransom, malice, or something else? What lessons did you learn about web hosting and digital security? How did that experience affect your approach to business and leadership? What did you do differently when launching Yeseo? How do you now decide what to delegate versus do yourself? What tools or systems help you delegate effectively? How did you get into SEO in the first place? What's the biggest mistake companies make when it comes to SEO? How has SEO evolved, especially with the rise of AI? Does Google penalize AI-generated content, or is quality still the priority? Why does “snake oil” SEO still persist? Tell us about your podcast, The Business Amplifier . Who is it for? Who do you think is the greatest band of all time—and why?…

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How Busy Teams Can Better Execute Growth Plans: Andrea Jones on 'Executagility' and Mistakes 14:20

28 days ago14:20

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In this special bonus episode of My Favorite Mistake , Mark Graban talks again with Andrea Jones, Principal at AJC and CEO of The Executagility Company . Andrea was previously featured in Episode 105 , and she returns to discuss the release of her new book: The Executagility Field Guide: How Busy Teams Can Execute Growth Plans. Andrea shares a new “favorite mistake” involving lost data from a Typeform survey—an honest example of learning the hard way how software design can trip up even experienced business leaders. The good news? She caught the mistake, learned from it, and adjusted her systems to avoid similar issues in the future. We also dive into the four pillars of the Executagility model: Alignment – Are we clear on the goals and priorities? Available Time – Do our people realistically have capacity to execute? Competence – Do we have the right skills in-house or need help? Structure – Do we have a repeatable process to keep projects on track? Andrea explains how she applied her own framework to the writing and launch of her book—and how it’s helping mid-sized businesses get growth initiatives done without burning out their teams. "You can’t execute growth if your team is already stretched thin trying to handle today’s work." "Just because someone’s capable in their current role doesn’t mean they can drive transformation alone. That’s why the glue person—the project leader—is essential."…

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Burnout to Breakthrough: How La Tonya Roberts Found Harmony by Leaving Corporate Consulting 29:39

4 weeks ago29:39

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My guest for Episode #309 of the My Favorite Mistake podcast is La Tonya Roberts, the founder and CEO of Harmony Consulting Group . La Tonya is a fractional COO, HR consultant, and executive coach who helps women entrepreneurs scale their service-based businesses from six to seven figures through systems, strategic planning, and operational excellence. Before launching her firm, she built her career at top consulting organizations like Deloitte and Booz Allen, where she developed deep expertise in organizational change and operational leadership. EPISODE PAGE WITH VIDEO, TRANSCRIPT , AND MORE In this episode, La Tonya shares her favorite mistake—staying too long in roles she had outgrown, taking on too much responsibility, and ultimately burning out. After experiencing both physical and emotional fatigue, including a dramatic moment that sent her to the hospital, she realized that her tendency to overfunction in high-demand environments was unsustainable. Those hard lessons eventually led her to rediscover joy in her work by launching her own business focused on operational harmony and intentional growth. La Tonya explains how she now helps founders—especially women—build scalable, process-driven businesses without sacrificing their well-being. She also shares how she uses tools like ChatGPT to automate repetitive tasks and increase efficiency, both in her business and her clients'. We also talk about the importance of aligning systems, people, and strategy, and how La Tonya’s clients benefit from her experience in both large enterprises and nimble startups. Listeners will hear practical advice on avoiding burnout, building systems that run without you, and why "work-life harmony" may be a better goal than elusive "balance."…

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Mistakes vs. 'Stupidity': C.J. Stewart Breaks Down Life Lessons from Baseball to Social Justice 48:35

5 weeks ago48:35

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My guest for Episode #308 of the My Favorite Mistake podcast is C.J. Stewart , co-founder and Chief Visionary Officer at the LEAD Center for Youth , an Atlanta-based nonprofit focused on empowering Black youth through sports-based development. Before dedicating his life to mentorship and advocacy, C.J. was drafted twice by the Chicago Cubs and built a successful career as a professional hitting instructor and co-owner of Diamond Directors . He’s also the author of Living to Lead: A Story of Passion, Purpose, and Grit . Episode page with video and more C.J.’s “favorite mistake”? Becoming an avid runner. What started as a tribute to the life of Ahmaud Arbery turned into a transformational habit—one that reshaped his health, mindset, and mission. In this powerful conversation, C.J. unpacks the difference between mistakes and stupidity , explores the struggles that shape significance, and reflects on the emotional toll and systemic barriers faced by Black athletes. He also shares how running has helped him connect across generations, communities, and cultures. Throughout the episode, C.J. offers a candid and thought-provoking look at racism, leadership, and the need for real advocacy—not just good coaching. He shares insights from his own life as a player, coach, and nonprofit leader, challenging listeners to consider how we name and respond to problems, and why protecting others is at the heart of leadership. This is a conversation about growth, conviction, and using our platforms to make a difference. Questions and Topics: What’s your favorite mistake, and what did you learn from it? In what way was becoming a runner a mistake? How do you define the difference between a mistake and stupidity? How has running changed you—physically, emotionally, and socially? Did pursuing a career in professional baseball feel like a mistake in hindsight? What does LEAD stand for, and what is its mission? Why is advocacy more important than just good coaching? Why do you think there are so few Black players in certain positions, like catcher or pitcher? What needs to change in baseball to address racism and systemic barriers? What do you mean when you say you became “openly Black” in 2015? How does racism take an emotional toll on Black athletes, even those who succeed? Are MLB diversity programs effective, or are they falling short? What else needs to happen to create real change and equity in baseball?…

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How the NFL Is Reducing Head Injuries Without Losing the Kickoff: A Conversation with Dr. Thom Mayer 12:55

6 weeks ago12:55

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In this bonus episode of My Favorite Mistake , host Mark Graban welcomes back Dr. Thom Mayer , the longtime Medical Director for the NFL Players Association. Thom previously joined us in catch up on his original episode here 🌐 Learn more about Dr. Mayer and his work with the NFLPA 💡 Subscribe at MarkGraban.com/mistake…

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Selling Books Isn’t the Publisher’s Job: Terry Whalin What Authors Must Learn Early On 49:10

6 weeks ago49:10

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My guest for Episode #307 of the My Favorite Mistake podcast is Terry Whalin , an accomplished editor and author of more than 60 books, several of which have sold over 100,000 copies. Terry is the owner of Whalin and Associates , a communications firm, and he serves as an acquisitions editor for Morgan James Publishing . Drawing from decades of experience in both writing and publishing, Terry shares a favorite mistake that changed the course of his career—offering valuable insights for first-time authors and seasoned professionals alike. Episode page with video and more His most recent book is 10 Publishing Myths: Insights Every Author Needs to Succeed . Terry’s favorite mistake took place in 2007, when a high-profile publishing event jolted him into realizing just how little he was doing to promote his own books. Despite having secured multiple six-figure advances and a long list of published titles, Terry was receiving negative royalty statements—his books weren’t earning out. That wake-up call led him to take what he calls 100% responsibility for his own success, adopting a daily commitment to book promotion, content creation, and building an online presence. From that turning point, he launched a blog (now with over 1,700 posts), grew a substantial social media following, and became a consistent voice in the author education space. In the conversation, Terry and Mark explore the myths and realities of book publishing—especially the misconception that a publisher will handle marketing. Terry outlines how today’s authors must become active promoters, the importance of building an email list you control, and why giving away ebooks can actually drive print book sales. He also shares hard-earned lessons about evaluating publishers, avoiding scams, and understanding how traditional and independent publishing models differ. Whether you’re writing your first book or navigating your next launch, Terry’s insights are a masterclass in professional ownership and long-term thinking. Questions and Topics: What’s your favorite mistake? Was it just a bad assumption to think publishers would promote your book, or do they sometimes mislead authors? Is the idea that a publisher will handle marketing one of the common myths in publishing? What specific actions did you start taking after realizing you needed to take full responsibility for your book’s success? Are you actively guesting on podcasts and using social media today to promote your work? Do social media efforts actually help sell books—or is it more about visibility and exposure? What’s your take on claims like “#1 Amazon bestseller”—do those really help authors sell books? Can you explain how the Morgan James model differs from traditional publishing? Why do you ask authors to commit to buying 2,000 copies of their own book? What role does giving away ebooks play in driving print sales? What should authors consider when deciding between traditional, hybrid, or independent publishing? How can aspiring authors avoid getting scammed by predatory publishing companies? What’s the role of an acquisitions editor, and how do you evaluate submissions? Do pre-orders really matter for bookstore placement? Why should authors consider writing for magazines or newspapers to build their platform? Do you think authors give up too early on marketing their books? Is building an email list still essential for authors, even in the age of social media? Should authors be cautious about relying too much on platforms like Facebook or LinkedIn?…

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Losing Her Best Employee Was the Wake-Up Call Betsy Pepine Needed to Reinvent Her Real Estate Company 44:44

7 weeks ago44:44

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My guest for Episode #306 of the My Favorite Mistake podcast is Betsy Pepine , a serial entrepreneur in real estate and the founder of Pepine Realty. Betsy leads a top-producing real estate team consistently recognized by The Wall Street Journal and has built a family of companies that includes a property management firm, title company, real estate school, and a nonprofit. EPISODE PAGE WITH VIDEO, TRANSCRIPT, AND MORE She’s also the author of the 2024 book Breaking Boxes: Dismantling the Metaphorical Boxes That Bind Us , which explores the limiting labels and roles we assign ourselves—and how to break free from them. Betsy’s favorite mistake was starting her brokerage with no clear plan. What began as a solo effort out of her home unexpectedly turned into a team, and eventually a company—but without intentional structure or culture. That all came to a head when her trusted assistant resigned right before a long-overdue family vacation. Her assistant’s honest feedback—about the lack of family, growth, and purpose—was a painful but pivotal wake-up call. Betsy responded not by retreating, but by reading leadership books on her cruise, hiring a coach, and reinventing her company with clear values and a defined mission. In our conversation, Betsy shares how she rebuilt Pepine Realty around core values like family , impact , and growth . She talks about initiatives like creating a nonprofit to address housing affordability and designing career paths that include a rare salaried-agent model in real estate. We also discuss the power of learning from mistakes—including how her team shares “learnings” each week in a psychologically safe environment that accelerates growth and prevents repeated errors. Betsy’s story is about far more than real estate—it’s about leadership, self-awareness, and responding to failure with action. Her perspective will resonate with anyone building a team or culture where people feel seen, supported, and inspired to improve. Questions and Topics: What’s your favorite mistake? What did your assistant say when she resigned—and how did that become a turning point for you? How did you respond to that feedback, and what changes did you make in your business? What were the first steps you took to start shaping your company culture? Did you create your mission and core values on your own at first? How did you define and build a “sense of family” inside your business? What inspired you to create a nonprofit—and how does it fit into your overall mission? What’s the purpose behind your unique salaried agent role? How do you help team members shift roles if they’re not in the right seat? What’s the weekly “learnings” segment in your team meeting—and how does it support growth? How do you balance encouraging learning from mistakes without being careless? Do you use checklists or systems to help prevent mistakes? What prompted you to write Breaking Boxes , and what’s the core message of the book? How do we recognize when we’re stuck in a metaphorical box—and how do we step out of it? What are the main fears that keep people in those boxes? Can you share how fear of failure has influenced your thinking over time? What does it take to build resilience to change? What’s your approach to managing fear of loss—especially status or social connections? How did your connection with Barbara Corcoran come about? What lessons have you learned from Barbara as a mentor? What advice would you give someone thinking of starting a business without a clear plan? What do you think are the best reasons for someone to get into real estate? How do you view the role of a real estate agent during high-stress life transitions? How do you create consistency in values across your family of companies? How do you support women reentering society after incarceration—and what’s the deeper “why” behind that work?…

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How a ‘Happy Mistake’ Led to a Leadership Journey in ADHD Education — John Willson of SOAR 41:31

9 weeks ago41:31

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My guest for Episode #305 of the My Favorite Mistake podcast is John Willson , Executive Director of SOAR , the world’s premier outdoor adventure program serving youth with ADHD and learning disabilities. Episode page with video and more With over 30 years of experience, John is a passionate advocate for experiential education and life skills development through structured, strengths-based environments. SOAR, which stands for Success Oriented Achievements Realized , supports young people ages 8 to 25 through summer camps, boarding schools, and gap year programs focused on building confidence and resilience. John’s favorite mistake took place on Mount Katahdin, the northern end of the Appalachian Trail, where he unknowingly summited a false peak in poor weather conditions. Faced with a difficult decision—turn back through a dangerous route he already knew or forge ahead into unknown terrain—he pressed on despite worsening conditions. Although it was arguably the “wrong” decision in the moment, it led to a powerful sense of accomplishment and a safer descent than expected. John describes this as a “happy mistake” that taught him about risk, perseverance, and the sometimes unexpected rewards of pressing forward. In our conversation, John shares how this philosophy of “failing forward” underpins SOAR’s mission. He explains how their structured programs help kids with ADHD and learning differences build critical life skills, develop self-awareness, and form friendships—often for the first time. We also explore the importance of creating environments where neurodiverse individuals are supported, understood, and encouraged to take safe risks, with a strong network behind them. John and I also discuss the evolving understanding of ADHD, the challenges of diagnosis, and how labels matter less than building strategies that work. He shares practical advice for parents and adults alike, emphasizing the role of support systems, coaching, and compassion. Whether you’re a parent, educator, or someone navigating your own neurodiversity, this episode offers insights into how mistakes—when supported by reflection and community—can lead to breakthroughs. Questions and Topics: What’s your favorite mistake? Is it true that one of your most common mistakes is people misspelling your last name? Did you go back and climb Mount Katahdin again on a clearer day? What do you mean by “summit fever”? If that decision had led to a bad outcome, would it change how you reflect on it? What lessons did you take away from that pattern of decision-making? What are some ways the SOAR summer camp is tailored for kids with ADHD or learning disabilities? How much of the benefit comes from being with other kids who share similar strengths and challenges? How does being in that kind of environment help kids feel more accepted? How does SOAR help kids who struggle to make friends build relationships? When were you diagnosed with ADHD? How did that diagnosis shape your connection to SOAR and the work you do? How many SOAR staff members also have ADHD, versus being trained to support it? What kind of person tends to thrive on your staff? What’s your take on people wondering if they have ADHD or if it’s anxiety or something else? What matters more—getting a diagnosis or developing the right coping strategies? What advice would you give someone recently diagnosed with ADHD—or who suspects they might have it? Can you talk about the role of support systems in success for neurodiverse individuals? What’s your view on younger people being more open about neurodiversity in the workplace? Can you share some practical first steps after receiving an ADHD diagnosis? Why is identifying your support network such a crucial part of success?…

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Why Staying Silent Was Her Favorite Mistake: Dr. Tia Warrick on Career Growth and Speaking Up 43:11

9 weeks ago43:11

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My guest for Episode #304 of the My Favorite Mistake podcast is Dr. Tia Warrick , a clinical research leader, epidemiologist, author, and entrepreneur who has spent nearly a decade working in the pharmaceutical and biotech industries. Episode page with video, transcript, and more She’s the founder of Lesous Consulting , a firm dedicated to supporting clinical research professionals and organizations through education, business analytics, and strategic consulting. With a strong academic background—including a doctorate in health science and clinical health education—Dr. Warrick is committed to empowering the next generation of researchers and bringing more awareness to the vast career opportunities within clinical research. In this episode, Dr. Warrick shares her "favorite mistake"—not speaking up for herself early in her career. She candidly reflects on a time when she took on significantly more responsibilities than her job description called for but hesitated to advocate for a promotion or raise. Her story highlights how staying silent led to missed opportunities and feelings of frustration. But more importantly, she explains how learning to take accountability and find her voice ultimately fueled her confidence, career progression, and entrepreneurial path. We also explore the broader challenges and opportunities within the clinical research industry, especially for early-career professionals who may not realize the variety of roles available. Dr. Warrick discusses the importance of mentorship, the need for greater visibility into clinical research career paths, and her motivation for writing Burst the Bubble , a book designed to inform and inspire future talent in the pharmaceutical world. She also touches on how she now teaches others to confidently advocate for themselves—whether during salary negotiations or while shaping their career direction. Questions and Topics: What’s your favorite mistake, and what did you learn from it? Was your early role as a clinical research coordinator before or after your advanced degrees? When did you realize you should have spoken up for yourself sooner? Was there a mentor or moment that helped you come to that realization? After receiving a small raise, did you try to advocate for more or take another path? Do you share this lesson with students or early-career professionals you mentor? How do you coach others on negotiating compensation and advocating for themselves? Why is it especially important to speak up early in your career? What are some misconceptions people have about roles in clinical research? How do you raise awareness about the breadth of opportunities in the field? How strong is the job outlook in clinical research, and how might AI impact it? What was the inspiration behind founding Lesous Consulting? What leadership lessons have you learned so far as a new entrepreneur? How do you create a culture where people feel safe to speak up and share feedback? What does psychological safety look like in your company and classroom? Can you tell us about the AI platform you’re developing and how it supports clinical research?…

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Why the Corporate Ladder Was My Biggest Mistake – Kason Morris on Redefining Work and Purpose 44:03

10 weeks ago44:03

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My guest for Episode #303 of the My Favorite Mistake podcast is Kason Morris , a corporate executive, speaker, coach, and self-described life-work revolutionary . With a career that spans consulting, financial services, and global learning and development leadership, Kason has spent years helping organizations and individuals prepare for the rapidly evolving world of work. He’s also the author of LifeWork Revolution: How to Unplug from the System, Find Your Purpose, and Thrive Beyond the 9 to 5 . Episode page with video, transcript, and more Kason’s “favorite mistake” was what he calls the relentless climb—his belief that success was defined by job titles, constant hustle, and chasing the next promotion. While his resume showed success, his health, relationships, and sense of fulfillment told a different story. A powerful turning point came when his young daughter mimicked his busy, distracted behavior at home—forcing him to ask: Is this the version of myself I want to model? From that moment, Kason began a process of reflection and reinvention, applying design thinking to life and work. Mark and Kason explore topics like life-work synergy vs. work-life balance, how AI is reshaping the future of work, and why psychological safety and transparency are foundational for sustainable innovation. Whether you're a burned-out professional, a leader trying to engage your team, or someone curious about navigating change, this conversation offers inspiring lessons about slowing down, designing better systems, and living more intentionally. Questions and Topics: What is your “favorite mistake,” and why does it stand out to you? When did you first realize that your definition of success might be off track? What roles or promotions were part of that “relentless climb” in your career? Did you receive feedback from your family, or was your shift more self-reflective? What was the moment with your daughter that became a wake-up call? How did you start making changes after that realization? What does the phrase “designing a better life” mean to you in practice? How did your professional experiences in product and organizational design influence your life design approach? What is “life-work synergy,” and how is it different from work-life balance or integration? How did your new perspective influence your transition into your current role? How do you define the “future of work,” and what are the key capabilities people need to thrive in it? What are your thoughts on AI—especially how individuals can partner with it effectively? What are some common mistakes people or companies make when approaching AI and new technologies? What’s your take on the return-to-office debate and how it fits into the future of work? Why is employee experience becoming such a critical focus for organizations? What advice do you have for individuals trying to future-proof their careers? What do organizations need to do culturally to foster innovation and engagement? In your coaching practice, who typically reaches out to you—and how can they learn more?…

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Fired by a Tech Bro: How Getting Sacked from Postmates Launched Author Tash Doherty's True Career 41:42

11 weeks ago41:42

41:42

My guest for Episode #302 of the My Favorite Mistake podcast is Tash Doherty , a British-Irish-American author, blogger, and podcaster currently based in Mexico City. A graduate of the Wharton School at the University of Pennsylvania, Tash previously worked in analytics for Postmates and Vox Media. Episode page with video, transcript, and more Today, she is the creator of Miss Educated —a popular blog and podcast covering business, pleasure, and women's health. Tash is also the author of the coming-of-age young adult novel These Perfectly Careless Things , self-published in 2023. She gained viral attention on TikTok by openly sharing her experiences with birth control. Fresh out of Wharton at age 23, Tash joined Postmates in San Francisco, working in analytics. When offered a team change, Tash ignored her gut instinct and reluctantly joined a team run by a manager whose working style clashed sharply with her own. Within months, their professional relationship deteriorated, leading to Tash's unexpected firing just two weeks before the company conducted widespread layoffs. Initially painful, this mistake forced Tash to reassess her career direction, ultimately opening the door to writing, entrepreneurship, and creative independence—turning a devastating setback into her favorite mistake. In this episode, we also discuss Tash’s insightful critique of technology companies and their unintended contributions to economic inequality, her process of transforming a teenage passion project into a published novel, and practical advice on balancing creativity with financial sustainability. Questions and Topics: What’s your favorite mistake? Were there early signs of trouble with your boss, Sumit, or did problems develop later? How did you choose Postmates as your first job after graduating from Wharton? Did your poor relationship with Sumit impact your job performance? Was it hard to trust another company or manager after that experience? Did you ever consider starting your own company again after leaving Postmates? Do entrepreneurs have a responsibility to reduce economic inequality, or is that up to policymakers? What specific mistakes do you see tech companies making right now? What led you to write your article, "How Tech Is Ruining the World"? Can you elaborate on how tech companies like Postmates worsen inequality? What did you mean when you described tech workers as being "incurious about the machine"? Is the tech industry truly improving society or causing greater harm? How should entrepreneurs or policymakers handle technologies that cause harm when scaled? Tell us about writing your book, These Perfectly Careless Things —how did it evolve over time? How do you decide when your writing is finished and ready to publish?…

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Overcoming Setbacks: Jonathan Small on the Career Mistake That Sparked His Success 45:22

12 weeks ago45:22