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

My Favorite Mistake: Business Lessons from Failures and Success

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?