Not everyone feels finished when their career ends, especially people who are wired to build.

This week, I'm joined by Randy Gage, an entrepreneur, author, and speaker who retired at 40 and realized he wasn't done creating. Stepping away from work didn't bring the sense of completion he expected, so he returned to building businesses, writing, and teaching. Not because he had to, but because he wasn't done.

That instinct to question what comes next started much earlier. At 15, Randy was sitting in a jail cell, facing the consequences of a life that had gone off track. That moment forced him to rethink his direction, and he's been asking those same questions about what comes next ever since.

We talked about:

How a stint in jail at 15 forced Randy to rethink his life

Why early beliefs shape how we think about money, relationships, and health

What Randy learned after retiring at 40 (and why he went back to work)

The difference between a finite game and a life built around purpose

How Randy defines prosperity beyond money

What it means to age with intention and resilience

Resources:

https://www.randygage.com

Breakthrough U

Randy on X

Randy on LinkedIn

For many men, leaving behind a career also means leaving behind a sense of identity. And much of our response to that change is shaped long before retirement ever enters the picture.

My guest today is Brian DesRoches, PhD. He's a psychotherapist, coach, and author whose work focuses on how the brain responds to change. With more than 30 years of experience, Brian helps people understand why self-doubt and disorientation often show up during major transitions.

We look at how long-standing emotional patterns can surface after work ends. Brian offers a way to see these reactions not as personal failures, but as learned responses that can finally be brought into the open.

In this episode, we covered:

Why identity loss can feel more unsettling than we expect

How early emotional learning shapes our response to change

What anxiety is often trying to protect us from

Why so many men struggle without the structure of a professional role

The emotional barriers to forming new connections

How awareness can create room for something new

Resources

www.briandesroches.com

Living a Trigger-free Life

What does it really take to age well—and why do so many people struggle with this transition after work?

Today's guest is Ken Stern, author of Healthy to 100 and a researcher focused on aging, longevity, and social connection. Ken has spent years studying why some people remain healthy and engaged later in life, while others face isolation and decline.

Ken explains why Americans struggle with aging and retirement more than people in other countries… and what we get wrong about life after work.

In this episode, we discuss:

Why aging in America often leads to isolation after work

What other cultures get right about belonging later in life

The surprising benefits of continuing some form of work

Why staying busy isn't the same as living well

What longevity research overlooks about human connection

Resources:

Healthy to 100 by Ken Stern

The Longevity Project