The First Months After Leaving Your Business

Stepping away from a career that has defined you for decades is rarely a clean break. For founders and professionals alike, retirement isn't just leaving the work behind. It means untangling identity, habits, and a sense of responsibility that doesn't simply turn off. My guest today is Dave Yeske, co-founder of Yeske Buie. After more than 35 years in financial planning, he and his wife made the intentional decision to step away from the firm they built together. As Dave shares, even a well-planned transition doesn't remove the emotional weight of letting go. We explore what it means to build something you can eventually leave—and what unfolds after you do. In this episode, we covered: What makes it so difficult for founders to step away The gap between knowing everything will be fine (and actually feeling it) Why retirement can bring unexpected emotions How identity is often tied to professional roles more than we realize Why meaningful moments in this stage of life don't have to be big to matter How joy can become a useful filter for deciding how to spend your time Resources: Retirement Plan (an Oscar nominated short film from The New Yorker)

You can listen to The First Months After Leaving Your Business online on Radio and Podcast. Open the player on this page to stream the available audio.

The First Months After Leaving Your Business is an episode from Chapter X with Michael Kay by Michael F Kay.

This episode is 47:27 long.

This episode was published on Apr 22, 2026.

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