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

After decades of work, Don Akchin found himself with too much time and very little structure.

That moment marked the beginning of a new kind of work for Don: paying attention to what happens when careers end and the familiar routines of life fall away.

Don Akchin is a writer and researcher who retired at 66 and began reflecting on his own experience alongside conversations with others navigating life after work.

Over time, those observations became the foundation for his book The AfterWork, which explores how people find meaning, connection, and direction beyond their careers.

We cover:

Why the loss of structure can be one of retirement's biggest surprises

How identity shifts once work is no longer central

What Don learned from listening to others' retirement stories

Why resilience matters more than having a perfect plan

How Don rebuilt structure after leaving work

Resources:

Visit Don's website

Follow Don on LinkedIn

The AfterWork on Amazon

Read The EndGame on Substack

Some people move through life by following a plan. Others move forward by paying attention to what holds their interest.

Today's guest, David Litt, spent more than three decades in the U.S. Foreign Service, working and living around the world. Along the way, he built a life shaped by language, learning, and a deep interest in how people and cultures function.

After retiring from government service, David didn't step away from engagement. Instead, he found new ways to teach, mentor, and share what he's learned, proving that purpose doesn't end when a career does.

In this episode, we covered:

What first drew David toward languages and life abroad

How curiosity shaped his path into the Foreign Service

The realities of representing the U.S. in unfamiliar places

One early experience that changed how he viewed diplomacy

Why teaching became a natural next chapter after retirement

David's advice for staying intellectually engaged later in life

Doug Fleener woke up on an airplane with no idea how he got there. That was the moment his life began to change.

Today, Doug shares the story of hitting bottom and rebuilding his life one decision at a time. He reflects on addiction, recovery, and the importance of learning how to pause before reacting.

Today, Doug is an author and speaker whose work centers on a simple but powerful question: What if? We talk about how that question creates space for perspective and action, especially during major life transitions.

We discuss:

The moment Doug realized his life needed to change

Why hitting bottom didn't immediately lead to transformation

How asking one simple question interrupts old patterns

The role of identity and routine during life after career

Why action matters more than insight alone

Resources

Get a free book excerpt at StartWithWhatIf.com

Visit DougFleener.com

As we move into the later chapters of life, many of us begin to think differently about health. Not just how long we'll live, but how well we'll live. What if the symptoms we accept as "normal aging" are actually signals pointing to something deeper?

In this episode, I'm joined by Reed Davis, a double board-certified holistic health practitioner and founder of Functional Diagnostic Nutrition. Reed helps people understand what's really happening inside their bodies by looking beyond standard lab work and surface-level symptoms.

In this episode, we discuss:

Why standard blood work often misses early warning signs

The difference between treating symptoms and addressing root causes

How stress, diet, and lifestyle quietly shape long-term health

What aging well really requires beyond diet and exercise

Why having purpose may be one of the most overlooked health factors

Learn more and access Reed's free workshop at: fdntraining.com/kay

Visit Reed's website

Follow Reed on Instagram

Watch on Youtube

Follow on LinkedIn

Why is it often easier to know what we don't want than to ask for what we do?

In this episode, I'm joined by Paul Quinn, author of The Big Ask: Unlock the Possibilities in Your Work Life and Dreams with Courageous Requests. Paul began his career as an actor before moving into corporate training and writing, where he became fascinated by the moments that spark real change.

Today, we explore how identity, fear, and unspoken rules shape the choices we make. Paul also shares stories that show how a single, well-timed question can open doors we didn't know were there.

You'll hear about:

How asking the right questions can help you reconnect with what you actually want

Why redefining identity after work can feel so disorienting

The trap of focusing on what we don't want (instead of naming what we do)

How fear and perfectionism can limit what you're willing to try

A simple question that can shift how we imagine what comes next

Mentioned

Visit Paul's Website

The Big Ask: Unlock the Possibilities in Your Work Life and Dreams with Courageous Requests

Follow Paul on Facebook