We’re going back to Episode 30 from January 2021, featuring Katie Anderson — author of Learning to Lead, Leading to Learn — and Isao Yoshino, the longtime Toyota leader whose career and lessons inspired her book.

Episode page with video, transcript, and more

It was such a privilege to talk with them then, and even more meaningful now, because I recently got to spend time with Mr. Yoshino in Japan last October during Katie’s Learning to Lead, Leading to Learn experience. Seeing him there — humble, curious, and still passionate about developing others — really reinforced everything we talked about in that episode.

Mr. Yoshino shared a story from early in his Toyota career, when a mistake on the shop floor could have led to punishment, but instead led to learning. His leaders didn’t blame him — they worked with him to fix the system. That experience shaped how he led and coached for decades.

Katie shared her own favorite mistake — a story about feedback early in her career that helped her realize the power of listening, asking questions, and helping others find their own answers.

Together, we explored what it means to create a culture where people feel safe to learn, improve, and grow — the kind of culture that turns mistakes into progress.

My guest for Episode #328 of the My Favorite Mistake podcast is Emily Aborn, a small business copywriter, speaker, and host of the Small Business Casual podcast.

Episode page with video, transcript, and more

Emily helps entrepreneurs bring clarity, creativity, and authenticity to their marketing. Before finding her true calling, she owned a brick-and-mortar organic mattress store—a business that looked great on paper but didn’t align with her passions or strengths.

Emily shares how this “perfect-on-paper” business became her favorite mistake. Though the store was profitable, she found herself feeling trapped, unfulfilled, and disconnected from the work she truly loved. Through closing that chapter, Emily discovered what she actually enjoyed most—writing, connection, and storytelling—and turned those insights into a business built around her natural skills.

Today, Emily works with entrepreneurs across industries to find their authentic voice and create meaningful marketing. In this episode, she and Mark explore lessons about self-awareness, alignment, and how mistakes can guide us toward a more fulfilling path. Emily also shares practical insights on copywriting, understanding your audience, and why genuine collaboration beats fear-based marketing every time.

• What was your favorite mistake, and what did you learn from it?
• Why did that business seem like such a good idea on paper?
• What made you realize it wasn’t the right fit?
• How did running that store help you discover your passion for copywriting?
• What were some of the marketing lessons you learned from that experience?
• What are the most common copywriting or branding mistakes you see small businesses make?
• How can business owners find and express their authentic voice in their marketing?
• What are “problem-aware,” “solution-aware,” and “symptom-aware” customers—and why does that matter?
• How do you approach repurposing content the right way instead of just copying and pasting?
• What has hosting your own podcast taught you about communication and creativity?
• Have you ever made a memorable mistake as a podcaster yourself?

My guest for Episode #327 of the My Favorite Mistake podcast is Dr. Maya Ackerman, AI pioneer, researcher, and CEO of WaveAI. She’s also an associate professor of Computer Science and Engineering at Santa Clara University and the author of the new book Creative Machines: AI, Art, and Us.

EPISODE PAGE WITH VIDEO, TRANSCRIPT, AND MORE

In this episode, Maya shares her favorite mistake — one that changed how she builds technology and thinks about creativity. Early in her journey as an entrepreneur, her team at WaveAI created an ambitious product called “Alicia,” designed to assist with every step of music creation. But in trying to help too much, they accidentally took freedom away from users. That experience inspired her concept of “humble AI” — systems that step back, listen, and support human creativity rather than take over.

Maya describes how that lesson led to their breakthrough success with Lyric Studio, an AI songwriting tool that empowers millions of artists by helping them create while staying true to their own voices. She also shares insights from her research on human-centered design, the philosophy behind generative models, and why we should build AI that’s more collaborative than competitive.

Together, we discuss why mistakes — whether made by people or machines — can spark innovation, and how being more forgiving toward imperfection can help both leaders and creators thrive.

“If AI is meant to be human-centric, it must be humble. Its job is to elevate people, not replace them.” — Maya Ackerman

“Who decided machines have to be perfect? It’s a ridiculous expectation — and a limiting one.” — Maya Ackerman

• What was your favorite mistake — and what did you learn from it?
• What went wrong with your second product, “ALYSIA,” and how did that shape your later success?
• How did you discover the concept of “humble creative machines”?
• What makes Lyric Studio different from general AI tools like ChatGPT?
• How do you design AI that supports — rather than replaces — human creativity?
• What’s the real difference between AI and a traditional algorithm?
• How do you think about ethical concerns, like AI imitating living artists?
• What do you mean by human-centered AI — and how can we build it?
• Why do AI systems “hallucinate,” and can those mistakes actually be useful?
• How can embracing mistakes — human or machine — lead to more creativity and innovation?
• What are your thoughts on AI’s future — should we be hopeful or concerned?

My guest for Episode #326 of the My Favorite Mistake podcast is Dr. William Harvey, a manufacturing executive and university professor whose career is defined by developing people, strengthening systems, and driving organizational excellence. A proud U.S. Marine, William carries forward a deep tradition of service and leadership. He also serves as the chair for the 2026 AME International Conference in Milwaukee, hosted by the Association for Manufacturing Excellence (AME).

EPISODE PAGE WITH VIDEO AND MORE

William shares a powerful early-career story about a mistake that taught him lasting lessons about trust, humility, and psychological safety. When he accidentally derailed a customer order by taking home the wrong document, he feared the worst. Instead, his manager’s calm and compassionate response—and a customer’s extraordinary effort to make things right—changed how William thought about leadership forever.

Over time, William applied those lessons to how he leads teams and builds culture. He believes that leaders go first—by admitting mistakes, showing vulnerability, and creating space for others to experiment, fail, and learn. Through daily coaching cycles and methods like Toyota Kata, he helps people develop confidence in problem solving and take ownership of improvement. His goal: to build a workplace culture rooted in trust, respect, and continuous learning, where every person feels safe enough to speak up and strong enough to lead.

• Why trusting your team is critical to avoiding unnecessary errors
• How supportive leadership responses turn mistakes into growth moments
• The connection between psychological safety, continuous improvement, and Toyota Kata
• How to “go first” as a leader—admitting your own mistakes to build trust
• The link between physical safety and psychological safety in world-class organizations
• What leaders can learn from Paul O’Neill and his “zero incidents” mindset at Alcoa

In this bonus re-release, we revisit an important and timely conversation with Sabrina Moon, Founder and CEO of The Problem Solving Institute and a certified Dare to Lead™ facilitator.

Originally aired as Episode #35 of My Favorite Mistake, this conversation remains one of the most powerful and honest reflections on leadership, shame, and transformation.

Episode page with transcript and more

• Sabrina’s “favorite mistake” — using shame as a leadership tool in high-stress environments

• The culture of command-and-control leadership she inherited (and how she broke the cycle)

• How Brené Brown’s work on vulnerability and shame helped her lead differently

• The personal toll of shame-based leadership — on her team and herself

• Why self-awareness is a skill—and how we can build it

• The role of grace, compassion, and curiosity in becoming a better leader

“We use shame and the fear of shame to motivate, but I think in an unhealthy way. I would utilize shame because it was the last tool in my toolbox and I was desperate.” — Sabrina Moon

Sabrina is a leadership coach and consultant who helps organizations move from reactive command-and-control cultures to psychologically safe environments where continuous improvement and innovation can thrive.

Connect with her at ProblemSI.com or on LinkedIn.

As more organizations reflect on how culture impacts performance, engagement, and well-being, this episode offers essential insights for leaders at every level. Whether you're managing a team or transforming a system, Sabrina's story reminds us that who we are as leaders matters just as much as what we do.

My guest for Episode #325 of the My Favorite Mistake podcast is Phillip Cantrell, EVP of Strategy at United Real Estate, founder of Benchmark Realty, and author of Failing My Way to Success: Lessons from 42 Years of Winning and Losing in Business.

EPISODE PAGE WITH VIDEO, TRANSCRIPT, AND MORE

Phillip reflects on more than four decades of entrepreneurial ups and downs across printing, real estate, and related ventures. He openly shares how devastating mistakes—including putting “all his eggs in one basket”—forced him to reinvent his approach. What looked like a catastrophe in 2007–2008 became the turning point that fueled Benchmark Realty’s rapid growth to nearly 2,000 agents.

“Failure is going to happen. If you don’t make mistakes, you’re not doing anything.”

In this conversation, Phillip and I talk about the difference between scaling vs. scrambling, the dangers of playing “not to lose” instead of “playing to win,” and why documenting processes is essential for growth. He also explains why your only real competitor is “the man in the mirror” and how daily reflection helps him learn from mistakes and avoid repeating them.

This episode is packed with timeless lessons on leadership, resilience, and learning from failure—whether you’re in real estate or any other industry.

“If you play not to lose in business, you’re already losing.”

• What’s your “favorite mistake” from your career?
• How did putting “all your eggs in one basket” impact Benchmark Realty?
• What did you learn from losing agents and clients during the mortgage crisis?
• How did you develop the flat-fee brokerage model, and what risks did you see at the time?
• Did you ever doubt whether that new model would work?
• How did you rebuild Benchmark from five agents to nearly 2,000?
• Why is it important to look outside your own industry for best practices?
• What do you mean by the difference between scaling and scrambling?
• How does documenting processes create better outcomes?
• Why do you say your only real competitor is “the man in the mirror”?
• What role has reflection and journaling played in your leadership growth?
• What advice would you give younger entrepreneurs about learning from mistakes?

In this very special solo episode of My Favorite Mistake, Mark Graban breaks down the gloriously ridiculous — and surprisingly instructive — mistakes made by the characters in his all-time favorite film, This Is Spinal Tap.

With the long-awaited sequel, Spinal Tap II: The End Continues, now in theaters, Mark explores why Spinal Tap endures not just as a cult comedy classic, but as a brilliant satire of human behavior, team dysfunction, communication breakdowns, and leadership gone sideways.

And yes — these mistakes still matter, even four decades later.

From the Stonehenge measured in inches… To the foil-wrapped “courgette” in the pants… To the pod that wouldn’t open and the drummers who keep dying…

…these moments are funny because they’re true. And they’re great reminders that how we respond to mistakes matters more than pretending they never happened.

• Why This Is Spinal Tap is more than just a comedy

• The iconic “Stonehenge” prop mistake and what it teaches us about communication

• How real-life rockstars refused to drum in the sequel (because of the “curse”)

• Why remembering the courgette as a cucumber is itself… a mistake

• The brilliance of “We don’t have time for that” and the backstage loop in Cleveland

• Why doing what you’re told isn’t the same as doing what’s right

• Mark’s personal story of seeing the film 100+ times — starting with a VHS in high school

• 🎬 This Is Spinal Tap on IMDb

• 🎥 Spinal Tap II: The End Continues – Now in Theaters

• 📘 The Mistakes That Make Us by Mark Graban

• 💻 SpinalTarp.com – A curated list of character mistakes from the film

If you enjoyed this episode, make sure to subscribe, leave a review, and check out past episodes of My Favorite Mistake — where we talk to leaders, authors, entrepreneurs, and creatives about the mistakes that made them who they are.

🎙️ Listen on Apple Podcasts, Spotify, or wherever you get your shows.

My guest for Episode #324 of the My Favorite Mistake podcast is Trevor Schade.

Episode page with video, transcript, and more

Trevor began his career as a Lean Six Sigma Black Belt with a strong background in coding and process improvement. He consulted on business efficiency and outsourcing before shifting into real estate in 2008. After earning his license, he quickly built a top-performing team of 26 agents with zero turnover over five years. By leveraging a virtual admin team in the Philippines and innovative automation, Trevor’s group generated over a million dollars in commissions.

In late 2023, Trevor stepped away from leading that large team to focus on investing, advising, and teaching. Today, he speaks on topics including negotiation, time freedom, and real estate strategy, and he has launched Life Wealth courses to help others pursue similar goals.

In this episode, Trevor shares his favorite mistake: jumping into a multi-level marketing business at age 19. The venture wasn’t financially successful, but it transformed his mindset. For the first time, Trevor developed a daily reading habit that exposed him to classics like Dale Carnegie’s How to Win Friends and Influence People and Robert Kiyosaki’s Rich Dad, Poor Dad. Those books gave him a foundation in psychology, leadership, and long-term thinking that continues to influence his work.

We also explore:

• How lessons from Nebraska football and martial arts shaped Trevor’s resilience
• What Lean Six Sigma taught him about efficiency, quality, and leadership
• Why he focused on psychological safety and belonging to keep his team intact
• How he used outsourcing and automation to scale without burnout
• The importance of setting trajectories instead of rigid goals in business and life

Trevor’s story is a reminder that sometimes the most unprofitable ventures provide the richest education — if we’re willing to learn from them.

• What’s your favorite mistake?
• How did joining a multi-level marketing company at 19 shape your growth, even if it wasn’t financially successful?
• Did you ever think about leaving earlier, and was staying too long its own mistake?
• What lessons did you take from Nebraska football and sports about resilience and bouncing back?
• How did you first get into Lean Six Sigma and continuous improvement work?
• In what ways did Lean and coding skills help you scale your real estate business?
• What did you learn about leadership from running a 26-agent team with zero turnover?
• How did you create a culture of psychological safety and belonging for your team?
• Why do you emphasize inspiring people instead of “beating them over the head with metrics”?
• What role have outsourcing and automation played in your business success?
• You’ve said you set trajectories instead of rigid goals — what does that mean in practice?
• Looking back, how do you connect these mistakes and lessons to your current focus on investing, advising, and teaching?