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?