My Favorite Mistake: Business Lessons from Failures and Success

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

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.
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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?

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

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.
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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?

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

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?

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

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?

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

My guest for Episode #301 of the My Favorite Mistake podcast is Jonathan Small, an award-winning journalist, editor, podcast host, and producer based in Los Angeles.
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As president of Strike Fire Productions, he has built a diverse career that spans magazine editing at top publications—from Child Magazine to Maxim—and pioneering roles in digital media and podcasting. Known for his candid storytelling and willingness to embrace risk, Jon has transformed professional setbacks into defining career moments, including leaving a cushy executive role to reinvent himself in a rapidly changing media landscape.
He's also the podcast of a podcast called "Write About Now." Jon's also the author of a book with the same title.
In this episode, Jon recounts his bold decision to leave a high-flying magazine career in New York for a risky, low-paying production role in Los Angeles—a move that, despite its initial challenges (like parting with his beloved cat and facing financial uncertainty), ultimately redefined his career. He shares insights into the evolution of the publishing industry, the shift from print to digital media, and how even seemingly disastrous mistakes can pave the way for reinvention, new opportunities, and personal growth.
Jon also delves into his extensive experience as a writer and interviewer, offering practical advice on common pitfalls in writing and the art of “show, don’t tell.” He emphasizes the importance of embracing imperfect first drafts, the necessity of reading widely to hone one’s craft, and the value of authentic conversation in podcasting—whether as a host or a guest.
Throughout the episode, listeners are treated to vivid anecdotes from his career, tips for leveraging AI in writing, and reflections on how vulnerability and genuine curiosity fuel both compelling storytelling and effective interviews.

Questions and Topics:
What is your favorite mistake?
What prompted you to leave magazine editing for a role in film production?
Did you consider returning to New York after the move?
What was your role at the movie production company?
What are the most common mistakes rookie writers make?
Can you provide an example that illustrates the difference between showing and telling in writing?
What tips do you have for becoming a more effective interviewer?
Based on your experience, what advice would you offer to guests on a podcast?

Marketing Over Bourbon with Sheila Butler: Data-Driven Strategies & Bold Moves

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My guest for Episode #300 of the My Favorite Mistake podcast is Sheila Butler, a Chief Marketing Officer with over 25 years of experience shaping integrated marketing strategies, building global loyalty programs, and driving customer engagement across both B2C and B2B sectors. 
She's the founder of Butler Marketing Group. Her track record includes leadership roles at Disney, JPMorgan Chase, Choice Hotels, and Axiom Bank.
She has a Bachelor of Science in Music and Business/Arts Administration from Indiana University and an MBA from UNC’s Kenan-Flagler Business School.
Today, Sheila shares her unique journey from a childhood passion for music and a stint at Disney, where she learned valuable lessons about the trade-offs between passion and pay. Despite a career start marked by lower-than-expected salaries and tough financial realities, she found that the relationships and experiences she built were invaluable. Her candid storytelling reveals how her early experiences taught her the importance of seizing opportunities—even when they seem like mistakes in the short term—to build a network that ultimately became a cornerstone for her current success.
Now, as the founder of Butler Marketing Group and host of her new podcast, "Marketing Over Bourbon," Sheila focuses on leveraging data-driven strategies to guide marketing decisions. She emphasizes creating safe spaces for experimentation, the power of testing and learning, and the need to balance strategic objectives with creative expression. Interwoven with her passion for bourbon, Sheila’s insights on marketing resonate with listeners who appreciate both practical advice and a genuine, relatable approach to career growth.

Questions and Topics:
What's your favorite mistake?
What are you drinking?
Do you prefer a bourbon Manhattan or a rye Manhattan?
Have you worked with any small distillers or distilling companies?
What drove you to launch your company?
How do you handle it when data contradicts expectations?
What trends are you seeing with companies becoming more data-driven in marketing?
Is half of your ad spend wasted, or is that changing with improved data insights?

Transforming Brilliant Jerks into Leaders: Luis Velasquez’s Coaching Strategies and Resilience

My guest for Episode #299 of the My Favorite Mistake podcast is Luis Velasquez, an executive coach in Silicon Valley and a Stanford Graduate School of Business facilitator. He's also the founder of Velas Consulting.
Episode page with video, transcript, and more
Once a university professor and research scientist, Luis helps mid-level managers to C-suite executives around the world learn, adapt, grow, and thrive by helping them how to reframe their challenges and take the most beneficial next step. 
His new book, available now, is Ordinary Resilience: Rethinking How Effective Leaders Adapt And Thrive.
Luis is a contributor to Harvard Business Review and Fast Company, and was featured in best-selling author Dorie Clark’s book, The Long Game. An avid endurance athlete, he runs marathons, ultra marathons, and ironman triathlons. 
In today's episode, Luis shares his journey from being a university professor and research scientist to becoming a trusted leadership coach in Silicon Valley and a facilitator for the Stanford Graduate School of Business. Luis discusses his new book, Ordinary Resilience: Rethinking How Effective Leaders Adapt and Thrive, and outlines his unique resilience formula—commitment plus persistence multiplied by optimism. He explains that resilience isn't about bouncing back but about unlocking the inherent ability to adapt and thrive by continuously reframing challenges and learning from experiences.
Luis also opens up about a significant mistake in his coaching career. He recounts a time when he delivered 360-degree feedback in a way that was too direct and decontextualized, which led a client to become defensive and ultimately resulted in his contract being terminated. This experience taught him the importance of providing feedback within the context of an individual’s aspirations and personal growth, rather than simply relaying raw perceptions.
The conversation further explores his approach to transforming challenging personalities—like the so-called “brilliant jerks”—into effective leaders, and how embracing and learning from mistakes is key to unlocking resilience and driving both personal and professional growth.

Questions and Topics:
How long is an ultramarathon compared to a standard 26.1-mile marathon?
Given your diverse career, what is your favorite mistake—and what did you learn from it?
Should we express our degree of certainty when stating facts?
How do you define resilience in leadership?
How do you identify and connect with high-value, challenging employees—is it via referrals or direct outreach?
How often do you coach not only the “brilliant jerk” but also intervene with their teams?
What role does fear play as a catalyst for growth—is it simply about reframing it?
Have you observed leaders effectively fostering optimism among their teams?
What does “embrace the suck” mean to you, and why is it a pivotal concept in your book?

General Hospital Actor and QVC Host Andy Paige Turned a Bold Misstep into a Beauty Revolution

My guest for Episode #298 of the My Favorite Mistake podcast is Andy Paige. She's a soap opera actress, podcast host, QVC guest host, and national beauty/image/lifestyle expert. As Pearl on ABC's General Hospital, she brings real-life QVC flair to captivating audiences with innovative advertising.
Episode page with transcript, video, and more
She hosts “The Dating Lab with the Hillbilly Yenta,” where she explores modern dating challenges with humor and diverse guests. Her international bestseller, Style on a Shoestring, earned her the title “Budget Bombshell” and inspired frugal style makeovers on TV worldwide.
With standout appearances on NBC’s Celebrity Apprentice, Starting Over, and TLC’s Ten Years Younger, Andy is the go-to expert for red-carpet style and practical image advice. She also delights radio audiences nationwide with playful style tips and has launched successful product lines including her patented GirlyGoGarter® and related accessories.
In this episode, Andy shares the dramatic story of how a miscalculated cliff jump not only resulted in a severe injury but also sparked a journey of innovation that led her to create the revolutionary Girly Go Garter. She reflects on the lessons learned from this life-altering mistake and discusses how it transformed her approach to both her career and personal growth.
She offers insights into the creative process behind her products, the challenges and triumphs of working in fast-paced television environments, and how embracing mistakes can lead to unexpected opportunities. Tune in for an inspiring conversation on resilience, reinvention, and the art of turning errors into stepping stones for success.

Questions and Topics:
What’s your favorite mistake?
Did you hit the edge of the rock when you jumped?
Was your foot catastrophically injured during the fall?
Did you expect a long rehab period and time away from the camera?
How many design iterations did the Girly Go Garter require—and is it still evolving based on feedback?
Did you try pitching your product on Shark Tank?
Did the Girly Go Garter play a role in landing your QVC gigs?
Is QVC always broadcast live?
How far in advance are soap opera episodes completed?
How did your role on General Hospital come about?
As a mother, how do you help your kids learn from mistakes?
Do you allow your natural accent to shine through on set?

Aviation Safety Explained: MIT’s Arnold Barnett on Why Flying Remains Incredibly Safe

In this special bonus episode of "My Favorite Mistake," host Mark Graban welcomes back Arnold Barnett, a renowned expert in aviation safety, to discuss public perception of air travel safety in light of recent air incidents. They explore common misconceptions about aviation risks, temporal fluctuations in safety data, and the factors contributing to the continuing improvement in aviation safety. Professor Barnett reassures listeners with data-driven insights and addresses the psychological biases influencing our perception of risk.
Episode page with video, transcript, and more
 
Key Discussion Points:
 
Public Perceptions vs. Reality: Arnie Barnett sheds light on why recent air travel incidents have caused public apprehension but insists that aviation remains incredibly safe.
 
Understanding Spasms of Events: Discussion on how statistical anomalies can lead to clusters of negative events but don't necessarily indicate a trend.
 
The Role of Probability: Barnett explains probability through coin toss analogies, emphasizing that rare clusters of events are expected even when the underlying system is safe.
 
Historic Comparisons and Data Trends: Insights into how aviation safety has followed a trajectory similar to Moore's Law, with risks decreasing significantly over decades.
 
Risks in Aviation: Highlighting the contrasts between accidental risks and potential threats from deliberate actions, such as terrorism.
 
Psychological Aspects of Risk: Exploration of how psychological biases, like availability bias, affect public perception of aviation risk.
 
Guest Bio:
 
Arnie Barnett
 
Arnie Barnett is the George Eastman Professor of Management Science at MIT Sloan School of Management and a pre-eminent expert in aviation safety. He has been recognized with the 2002 President Citation from the Flight Safety Foundation for outstanding contributions to safety and has received multiple teaching honors from MIT Sloan students. Barnett holds a BA in mathematics from Columbia University and a PhD in mathematics from MIT.
 
Previous Appearance: Arnie Barnett's favorite mistake story in Episode 169: https://www.youtube.com/watch?v=-ffe6bNtxlg
 
MIT Article: Explore the article on the MIT website detailing aviation safety trends and Moore's Law analogy, as discussed in the episode: https://news.mit.edu/2024/study-flying-keeps-getting-safer-0807
 
Memorable Quotes:
 
"If you see a little kid at an American airport, then that kid...is five times as likely to grow up to be president as to perish in the forthcoming flight." — Arnie Barnett
 
"Fears are deep, and when I respect them, I know many people who are afraid to fly, but I believe this is something we shouldn't be afraid of." — Arnie Barnett
 
Actionable Takeaways from the Podcast Episode
 
Stay Informed, Not Anxious:
 
Guidance: Understand that aviation safety is statistically very high, even amidst rare bursts of incidents. Arnie Barnett explained that the risk levels are closer to zero than perceived, as discussed with the "availability bias" and the statistical explanation regarding recent safety events.
 
Implementation: Arm yourself with reliable safety data and trends when feeling anxious about flying. Remind yourself that the perception of risk is often inflated by isolated incidents, which are outweighed by the overwhelming safety record of aviation.
 
Leverage Sound Arguments:
 
Guidance: Use metaphorical insights, such as Barnett's coin analogy, to effectively communicate the nature of rare events. This helps in understanding that a sudden occurrence of incidents does not necessarily indicate a systematic issue.
 
Implementation: When discussing risks, employ similar analogies to articulate to others that rare sequences of events do happen without indicating a broader change in safety. This approach can not only assure others but also help you internalize and remain calm about flying.
 
Focus on Broader Safety Trends:
 
Guidance: Be aware that deliberate attacks are an area of potential concern, but reassurances on trends are clear from Barnett, who discussed continuous improvements and the extraordinary safety levels in countries like the US, UK, and Canada.
 
Implementation: When planning air travel, focus on the historical safety record of airlines and recognize that current safety measures are stringent and continuously improving. For example, choosing airlines with exemplary safety records can further mitigate rare and unanticipated risks, providing peace of mind during air travel.

Learning from Mistakes: Norman Wolfe’s Guide to Building High-Performing Teams

My guest for Episode #297 of the My Favorite Mistake podcast is Norman Wolfe, the Founder and CEO of Quantum Leaders.
EPISODE PAGE with video, transcript, and more
Norman's journey as both a successful executive and a trusted coach to countless leaders has been driven by one central question: How can we improve our ability to achieve the results we want? His pursuit of this answer led him to master a wide range of business disciplines—from leadership and strategy to operations and finance—while also deeply exploring human potential, personal growth, and even spirituality.
Norman's mission now is to help others transform their thinking and approach to more effectively achieve their deepest desires.
In this episode, I chat with Norman about how mistakes can spark profound growth and innovation in leadership. Norman shares his favorite mistake story—from his early days as a first-time manager, where a harsh performance review challenged him, to the lessons that fueled his journey toward becoming a top leader at Hewlett-Packard. He explains Wolfe's Law, his formula that highlights the exponential impact of relationships and context on achieving outcomes.
We also dive into the principles of quantum leadership, discussing how a holistic, people-centered approach—blending practical leadership with a touch of spirituality and systems thinking—can transform organizations into dynamic learning ecosystems.

Questions and Topics:
What is your favorite mistake?
Did the negative review or your mentors provide specific, actionable feedback for improvement?
Is the formula you mentioned what you call “Wolfe’s Law”?
Could you state Wolfe’s Law for us?
Does your formula imply that relationships are exponentially more important than activity and context?
How does spirituality fit into your framework—does it fall under context or serve another role?
How do you assess whether individuals (or teams) are mature enough for increased responsibility?
What should be eliminated versus managed when dealing with ambiguity and risk?
From your experience, why is it essential to reframe mistakes as positive learning opportunities?
Do you believe that making mistakes fosters adaptation and growth?