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)

We don't spend much time thinking about how we listen.

​But if you've ever felt misunderstood or struggled to connect with someone, you've probably felt its impact.

Today, I'm joined by David Joseph, MD, a psychiatrist and psychoanalyst with more than fifty years of experience listening to people at a very deep level. He's devoted his career to something most of us struggle with: actually understanding what someone is trying to say.

​And for many men, especially in retirement or approaching it, this becomes more important than ever. When the structure of work falls away and relationships shift, we're left with more space to connect, or feel disconnected.

We covered:

• Why listening is more than just hearing words
• What we miss when we focus only on what's being said
• Why most of us aren't as good at listening as we think
• How learning to listen to yourself changes everything
• What gets in the way of deeper conversations
• Why relationships can feel harder after leaving work
• What it means to really understand another person
  

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Resources:

Listening for a Life: The Artful Science of Psychotherapy

We like to think we're making choices about how we live. But most of the time, we're just repeating patterns we've been running for years.

In this episode, I'm joined by Marcy Axelrod, who shares why those patterns are so hard to break and what it actually takes to start showing up differently in this next chapter.

Marcy's work explores how we show up in the world. Today, she introduces a 3-part framework for understanding how we operate—and why most of us are only partially present in our lives.

In this episode, we covered:

-Why most people are operating on patterns they don't even realize

-How decades of routine shape the way we see ourselves

-The difference between "just showing up" and being fully present

-Why stress and fear keep us stuck in old ways of thinking

-The idea that we're always playing multiple roles (not just one identity)

-A simple exercise to rethink who you are beyond your career

Resources

Website: www.ChooseToShowUp.com
Instagram: @MarcyAxelrodArt
Instagram: @MarcyAxelrod