Leadership Love

Monday, September 14 - Tuesday, September 15, 2026

Online

LEADERSHIP LOVE AGENDA

Welcome & Opening Remarks
On grief, reinvention, and the leadership lessons nobody teaches you
This past year, I lost my father. I lost my mother-in-law. I stepped away from the company I co-founded and led for twenty-three years. I watched my city get militarized. I sent my kid into the world while the world was actively on fire. And somewhere in the middle of all of it, I was still expected to lead.
Nobody teaches you this part.
Read More
We’ve all been through a lot. The pandemic, the social unrest, the political chaos, the economic whiplash, AI. And it’s not over. For many of us, the cumulative weight of it all quietly narrowed our lives. We stopped planning far out. We stopped dreaming big. We got careful. We insulated ourselves from all the things.
Read More
Item description

Most of us have a highlight reel of moments we chalk up to being in the right place at the right time. Humble, sure. But that story has a cost. If luck got you here, it can take you out just as easily — and that’s the perfect breeding ground for imposter syndrome.
Read More
For a long time, I got really good at being a functional human inside systems that rewarded functioning. Creative leadership. Tech. Strategy. Performance. Achievement. From the outside, much of my life looked successful. Internally, though, there was a growing sense that I had become disconnected from something essential in myself. In the middle of shifting from design leadership into psychotherapy, while also rebuilding my own life in real time, I became increasingly interested in the possibility that burnout is not just depletion, but direction. Less about failure and more about feedback.
Read More
Life doesn’t schedule itself around your agency. A health scare, family crisis, burnout—or a sudden opportunity—can take an owner out of the day-to-day with zero notice.
Karl shares a simple “Be Prepared” approach to keep the agency steady before an emergency happens—and to act fast when it does. You’ll learn how to stabilize what must keep moving, assign backups and decision rights, de-risk what’s trapped in your head, and run a quick “succession drill” so the plan is real before you need it.
Read More

After three layoffs, Stephen Gates sat down to interview for his next big role and realized he hadn’t created work he was proud of in over five years.
He had become a politician, organizational therapist, interventionist, and executive hysteria coordinator. Not a creative. Not the kind of leader he’d set out to be. The salary was there, but the work and creativity had gone lost along the way.
Read More
Telling people about a life-altering diagnosis is terrifying. Unfortunately, it’s something most of us will have to do. In the United States, 66% to 75% of Americans suffer from one or more chronic illnesses: heart disease, cancer, diabetes, long COVID, or other illnesses.
Read More
Item description

Interviewed by Carl Smith

Most leadership stories end at the hard thing. The loss. The moment everything changed. But what happens after that? What does it actually look like to stop waiting to return to who you were and start figuring out who you're becoming
Read More