May 12, 2026
In this episode of On the Brink with Andi Simon, Andi speaks with Tonya Thomas, founder of Team Delegate, about how entrepreneurs and business leaders can delegate more effectively, scale their businesses, and stop becoming the bottleneck. They explore the difference between reactive and proactive executive assistants,...
May 3, 2026
Rethinking Retirement: Why It’s Never Too Late to Reinvent Yourself
Featuring Louise Olson
What happens when you step away from the role that once defined you? Why is this thing called "retirement" such a challenge?
For many, retirement feels like an ending. But in this episode of On the Brink with Andi Simon, my...
Apr 27, 2026
What happens when successful professionals retire—and realize they’re not ready to stop?
In this episode of On the Brink with Andi Simon, I speak with Vistage Chair Jeannette Hobson about the evolving meaning of retirement—and why so many people are unprepared for what comes next.
Jeannette shares her remarkable...
Apr 20, 2026
In this episode of On the Brink with Andi Simon, Lisa Woodruff, founder of Organize 365, shares a powerful reframe of what it means to be organized. Moving beyond clutter and to-do lists, she explores how organization is a learnable skill that can reduce "overwhelm", improve time management, and create space for purpose...
Apr 14, 2026
Summary
Retirement is often framed as a personal milestone—a moment when we step away from work and into freedom. But what if retirement isn’t just about leaving a job? What if it’s about navigating the deep relationships, identity shifts, and responsibilities we carry with us into what comes next?
In this...