A lot of people say they want to stay active or do work that still matters to them after they retire.

But then they rest, travel, or wait for the right opportunity to show up. Over time, that can turn into long stretches without structure or direction in life.

I'm really glad to welcome Lynn Friesth back to the show. He left corporate life in 2015 and has spent the last ten years helping others turn their experience into coaching, consulting, or project-based work in the next chapter.

We talk about:

• Why many people drift in retirement instead of designing what's next
• The idea of a "portfolio life" and moving beyond your job title
• Lynn's G.L.E.A.N. process for uncovering the value in your experience
• Why starting with identity matters more than starting with action
• The mindset shift from needing certainty to being willing to experiment
• How curiosity becomes an advantage as you move into something new
• Where AI fits in (and why experience still matters)

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Resources Podcast: "Creating Your Encore Life" - https://www.lynnfriesth.com/podcast Website: https://www.lynnfriesth.com LinkedIn: https://www.linkedin.com/in/lynnfriesth

Rusty Gardner realized he wasn't listening to his son during their phone calls. So he stopped what he was doing and went for a walk.

That new habit changed their conversations. Then it changed his mornings, and eventually it turned into something he couldn't ignore.

Rusty spends a lot of time reflecting on identity and the different "passages" we move through as we get older. Today, we explore what happens when you start paying attention to what actually feels different.

We discuss:

• How Rusty built a completely new career without a clear plan
• The moment he realized he wasn't fully present with his son
• How walking became a daily practice for connection and clarity
• What he's learned about identity through life's different decades
• His experience facing aging, mortality, and a major life "passage"
• Why following your energy can reveal what actually matters

Resources:

Just Walking: https://justwalking.com TikTok: www.tiktok.com/@justwalking.com Instagram: https://www.instagram.com/justwalkingwithrusty

Email:

[email protected]

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

For a lot of men, their social life is their job. So what happens when that job goes away?

In this conversation, Anthony Silard shares what he's learned studying loneliness and relationships—and why so many reach this stage of life without the connections they actually need.

He introduces the "four PRs" framework and how those roles shape identity for decades. The problem is, they leave very little room for friendships outside of work and family.

Once that structure disappears, many men find themselves starting from scratch.

You'll hear about:

-The moment a retired executive tried to go back to the office… and couldn't get in

-Why work relationships often don't carry over after retirement

-The "four PRs" that shape identity (and what they leave out)

-Why men often rely on their partner as their entire social network

-A striking stat on what happens to men vs. women after losing a spouse

-Why some of the loneliest people are surrounded by others

-What leaders do that builds real connection (and why it has nothing to do with confidence)

Resources

Download Anthony's free books: theartoflivingfree.org/freehappinessandfriendshipbooks

Available on Amazon: Love and Suffering: Break the Emotional Chains that Prevent You from Experiencing Love

Most people go looking for purpose when they feel lost. J.D. Pincus believes that's not where we should start.

JD is a social psychologist, researcher, and author of The Emotionally Agile Brain. He's spent decades studying what humans actually need and mapped it into a framework that helps explain why people can feel adrift, even after achieving everything they set out to do.

Today, he joins us to talk about those needs and why getting unstuck might start with feeling a little worse before you feel better.

You'll hear about:

-Why people can feel stuck even when life looks fine

-How loss of social connection impacts stability and direction

-Why this transition can be especially challenging for men

-JD's framework of 12 core emotional needs

-Why feeling stuck often comes from unmet needs

-Why purpose doesn't always come first

Resources:

Book: The Emotionally Agile Brain

LinkedIn: J. David Pincus

Website: AgileBrain

We're often told that declining health is just part of getting older. But what if that's not actually true?

In this episode, I'm speaking with Dr. Darren Clair, a physician with over 40 years of experience who has spent the last 25 years helping people take a more proactive approach to their health.

After seeing the limits of a system focused on diagnosing and prescribing, Darren chose a different path. His work centers on lifestyle, education, and helping people stay healthy in the first place.

We'll hear how his perspective evolved over time, what he's learned along the way, and why it's never too late to improve your health.

• Why Darren moved away from traditional medicine

• How the current system focuses on treating symptoms

• The role lifestyle plays in long-term health outcomes

• Why many people don't take action until later in life

• The difference between prevention and a proactive approach

• Why better health often feels like gaining something (not giving something up)

Resources:

Dr. Clair's Book: Creating a Life of Vibrance

Facebook: facebook.com/VibranceHealth

Instagram: instagram.com/vibrancehealth

Most of us spend the first half of life building. The second half, if we're paying attention, is when we start asking whether we built the right things.

Rand Selig is back on the show and a lot has changed since his first appearance two years ago. What started as a few early conversations has since grown into 100+ interviews and the continued success of his book Thriving, which he recently narrated as an audiobook.

Rand spent much of his career running his own investment banking firm. Now he's turned his attention to the questions that tend to matter most in life's later chapters: relationships, legacy, and what it looks like to truly live well.

You'll hear about:

• How a simple habit made him a better listener (and changed everything)

• The self-reflection practice he uses to actually measure his own growth

• What finally pushed him to start writing Thriving

• Why your purpose doesn't have to be big to be meaningful

• The real difference between success and thriving

• Why curiosity is one of the best predictors of a good later life

Resources

Website: www.randselig.com

LinkedIn: Connect with Rand

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