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.”

🎙️ 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:

🎧 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.”

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.

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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.

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.

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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.

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.

My guest for Episode #316 of the My Favorite Mistake podcast is Jim Schleckser, founder and CEO of The CEO Project.

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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.

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.

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.”

📕 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.

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My guest for Episode #314 of the My Favorite Mistake podcast is Mark Struczewski, also known as “Mister Productivity.” Mark is a Houston-based productivity coach, speaker, and host of The Mister Productivity Podcast, with over 1,300 episodes to his name. He helps overwhelmed professionals cut through distractions and focus on what truly matters.

Episode page with video, transcript, and more

But before becoming a go-to expert on focus and effectiveness, Mark made a classic entrepreneurial mistake: thinking that launching a website would instantly attract a stream of clients. Spoiler alert—it didn’t.

Mark’s favorite mistake was stepping into solopreneurship with unrealistic expectations. After being fired from his corporate job in 2005 and officially launching his business in 2011, he quickly found himself burning money on coaches, conferences, and tools he didn’t need—without any real plan or payoff. The financial pressure eventually forced a mindset shift: instead of trying to do everything, he began focusing on the right things at the right time. That turning point not only saved his business—it became the foundation for his productivity philosophy.

In our conversation, Mark shares hard-earned lessons about clarity, focus, and sustainable productivity. We explore how he helps clients move past the illusion of “busyness,” why joy is an essential ingredient for productivity, and why it’s okay to slow down or even stop when your body and brain need a break. Mark also offers insight into how he uses tools like ChatGPT to streamline content creation and why being intentional with time is more powerful than packing your schedule. Whether you're a solopreneur or leading a team, this episode will challenge how you define and pursue productivity.