Larry Kesslin spent much of his life chasing success. After leaving corporate America at 29, he built a successful career as an entrepreneur advising business owners across the country.

By most standards, he had freedom, financial stability, and the life he once thought he wanted. Yet something was still missing. In this episode, Larry shares the moments that changed how he sees success.

A volunteer trip in Aspen and a later time in rural Uganda made him question the life he had built. Over time, he realized that chasing success was different from living with purpose.

In this episode:

How financial insecurity in childhood shaped his drive to succeed

The moment at GE that led him to leave corporate life

What he learned about happiness while traveling in Africa

The difference between success and significance

How our belief systems are formed and why they can be unlearned

Why aging gives us the chance to question identity

Resources:

Larry on LinkedIn
5-Dots
Joy Molecule

At 25, Guru Yogishivan was surrounded by luxury in the Middle East. He had trained as a martial artist and become a boxing champion. By most standards, he had success.

But as he spent time around people who had money and influence, he noticed that no one seemed free from fear. Whether it was fear of loss, fear of death, or fear of not having enough.

So he began asking the people around him if they were truly happy. That question sent him on a very different path. In this episode, we explore his journey from athlete to monk... and what his search for truth might mean for men entering their next chapter of life.

We discuss:

What happens when success no longer feels like enough

Why your identity is constantly changing

Whether losing your career is actually losing yourself

What 24 minutes a day of inward focus might change

A disciplined daily practice for reconnecting with yourself

Resources:

Book an Ask Yogi Session

YouTube: Indimasi Healing Village

Facebook: Indimas Healing Village

Instagram: Indimasi Healing Village

Whatsapp: +91 62386 00274

Howard Rosenberg had done what many of us were taught to do. He got an education, built a career, and provided for his family. From the outside, it checked every box.

But in his early fifties, a diagnosis of advanced heart disease and emergency quintuple bypass surgery forced him to slow down and take a hard look at the life he had built.

That wake-up call led Howard to begin asking deeper questions about identity, purpose, creativity… and what really sustains us in the second half of life.

We talked about:

How a health wake-up call led to a complete identity shift

Why the way we finish the sentence "I am…" matters

The difference between external success and internal fulfillment

How creativity extends far beyond art

What it really means to consciously create your next chapter

Resources
Howard Rosenberg's Life Coaching

Howard on LinkedIn

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

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

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

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