Rethink Retirement with Jeannette Hobson

Rethink Retirement with Jeannette Hobson

From On the Brink with Andi Simon by Andi Simon

April 27, 2026 · 34 min · Season 7 · Episode 473

About this episode

This episode explores the evolving meaning of retirement and the importance of having a life plan beyond financial considerations.

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 journey of career pivots, lifelong curiosity, and leadership—and how those same qualities are essential for navigating life beyond work. We explore why retirement isn't an ending, but a transition—one that requires more than a financial plan. It requires a life plan. If you are thinking about retirement—or already there—this conversation will help you rethink what comes next. In This Episode: Why curiosity is the key to lifelong reinvention The hidden risks of retiring without a life plan How to prepare before you leave your role The importance of purpose, structure, and community Why "age is irrelevant" in designing your next chapter Connect with Andi Learn more about Dr. Andi Simon's work, books, and upcoming workshops: www.andisimon.com

People in this episode

Host: Andi Simon

Guest: Jeannette Hobson

Topics covered

  • retirement
  • career pivots
  • lifelong curiosity
  • life planning
  • purpose
  • community

Keywords

  • retirement
  • life plan
  • career transitions
  • curiosity
  • purpose
  • community
  • preparation

Mentioned in this episode

Organizations: Vistage

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