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