I sat down with Kelly Leonard, the legendary creative executive behind Second City, the theater that launched Tina Fey, Steve Carell, and Stephen Colbert.

We dig into the real origins of "Yes And," tracing it back from a social worker teaching immigrant kids in Chicago all the way to boardrooms and FBI hostage negotiators. Kelly breaks down why our default setting as humans is to say no, and why that instinct is quietly killing our creativity, our careers, and our relationships.

We talk about the Keith Jarrett Köln Concert story, the science of why introverts feel better acting like extroverts, and why the biggest barrier to innovation isn't failure, it's success.

What's one "no" you regret saying?

For a long time, staying busy made me feel like I had control. Five podcasts in a day, constant projects, always working, it felt like I was moving forward.

Then I slowed down and realized something uncomfortable: being busy and making progress are not the same thing. And when the work stopped, some of the anxiety I had been outrunning came right back.

I’m still figuring this out. For now, the goal is simple: control the things I can control and learn to let go of the rest.

I’ve always believed that some of the best leadership lessons come from places you wouldn’t expect, and in this conversation, I got to explore that idea with retired deputy fire chief and author Frank Viscuso. We talked about what firefighters can teach us about fear, pressure, teamwork, and leadership and why staying calm in a crisis isn’t simply something you’re born with. Frank explains how training, preparation, urgency, and what he calls “ruthless repetitions” can help us make better decisions when everything starts falling apart.

We also dug into trust and empathy, why great leaders inspire people instead of demanding loyalty, and how spending real time with your team can build stronger relationships. We talked about conflict, workplace drama, unresolved tension, and why teams can fall apart even when talented people are involved. One lesson that really stuck with me was Frank’s advice to “stop expecting you from other people.” Different people respond differently, and great leadership starts with understanding that.

What happens when you stop avoiding the hard things and start moving toward them?