Leadership: Fit, Experimentation, and Incrementalism

Why does it feel like everything is falling apart, even as our lives get materially easier in so many ways? Michael Hyatt talks with author and cultural thinker Virginia Postrel about why progress becomes invisible, how nostalgia for the “good old days” distorts reality, and why modern change moves unevenly.

They explore why humans crave beauty and meaning (not just function) and how AI is reshaping the future of work. A clear theme emerges throughout the wide-ranging conversation: change is inevitable, and how we respond matters. Resilience, margin, and an entrepreneurial mindset make all the difference.

If you’ve felt powerless against “big systems,” this episode is a reminder that innovation is often personal, practical, and close to home: start where you are, solve what you can, and expect the unexpected.

Memorable Quotes

1. “The issues of character never go away. They are eternal human questions, and we forget because we have sort of nostalgic views of the past.”
2. “Even the smartest AI can’t figure out what people want—what people are dissatisfied with. And a lot of innovation comes from that. We tend to focus on big technologies. And even big technologies come from a lot of incremental improvements… A lot of improvements come from people saying, ‘I’m dissatisfied with this,’ or ‘Here’s something I figured out.’”
3. “Human beings don’t just value function. They value pleasure, and they value meaning, and pleasure and meaning are things that are very much conveyed through the look and feel of objects or places.”
4. “Agency is problem-solving. It’s you solving problems in your life, or whatever that might be—and it’s sort of reversed, too, which is that if you assume that it’s someone else’s job to solve your problem, you sort of give up your sense of agency.”
5.  “A lot of leadership is figuring out what gifts individuals have and getting them moving in the right direction… A big part of leadership as problem-solving is people problem-solving—getting people in the right roles and thinking about how those roles mesh.”
6. “Expect that you’re going to be in a world that changes, because that’s the world we live in. It’s the world we’ve been living in for hundreds of years. The other thing is: understand this didn’t start with you. Other people have gone through amazing and scary and terrifying changes, and our civilization has lived to tell the tale.”

Key Takeaways

1. Progress Becomes Invisible Quickly. We normalize improvements fast—and forget what life used to require in drudgery, time, and basic comforts.
2. Change Is Uneven: Bits vs. Atoms. Software accelerates rapidly, while physical-world progress (like housing) can be slowed by policy, cost, and complexity.
3. Dynamism vs. Stasis Shapes How We Face the Future. Some people see change as positive-sum opportunity; others experience it as zero-sum threat.
4. Agency Grows Through Problem-Solving. When we assume “someone else” must fix things, we trade away our sense of control and possibility.
5. Resilience Requires Margin. Financial cushion, emotional bandwidth, and community support help you absorb shocks and adapt.
6. Entrepreneurship Is Bigger Than Business. You can be “entrepreneurial” by starting groups, building community, or solving everyday problems—not just launching companies.

Resources

• vpostrel.com (Website)
• vpostrel.substack.com (Substack Newsletter)
• The Future and Its Enemies (Book)
• The Substance of Style (Book)
• The Power of Glamor (Book)
• The Fabric of Civilization (Book)

Watch on YouTube at:  https://youtu.be/yCMHIdYYS-A

This episode was produced by Sarah Vorhees Wendel of VW Sound