What if the things you loved most as a kid still hold clues about the life you actually want now?

I still remember Yankees games crackling through a transistor radio tucked under my pillow long past bedtime. For Ben Orlando, it was realizing those moments were never really about baseball at all.

I'm talking with psychotherapist, writer, and Midnight Library of Baseball host Ben Orlando about masculinity, nostalgia, and what happens when men lose the thread back to themselves.

We explore why the hobbies we dismiss as "not serious" often point to something much deeper, and why reconnecting with joy and authenticity matters even more as we get older.

You'll hear about:

• Why certain childhood memories stay with us for life
  
  
• How men lose themselves in careers and responsibilities
  
  
• The importance of reconnecting with joy and nostalgia
  
  
• Why hobbies and passions matter more than we think
  
  
• The emotional power of shared memories
  
  
• What older men regret most at the end of life
  
  
• Why it's never too late to reconnect with yourself

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Resources

• Podcast: Midnight Library of Baseball
  
  
• Website: midnightlibraryofbaseball.com
  
  
• Instagram: @midnightlibraryofbaseball
  
  
• Therapy: benorlando.com

Many fathers spent their lives learning how to provide for their families. But emotional connection often became much harder to pass down.

My guest today is Marc Azoulay, therapist and founder of Men's Therapy Online. Marc works with men navigating relationships, identity, purpose, and emotional health across different stages of life.

In this episode, Marc shares his own journey through addiction, recovery, and self-discovery. We look at the emotional disconnect many men experience with themselves, their children, and each other.

You'll hear about:

• Why Marc believes many men were never taught emotional connection
  
  
• The frightening turning point that forced him to reevaluate his life
  
  
• How different generations of men struggle with identity, work, and purpose
  
  
• The reason why emotional openness between men still feels uncomfortable
  
  
• How curiosity can help parents strengthen relationships with adult children

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Resources:

Mens Therapy Online

What happens when life forces you into a chapter you never planned for?

After decades building a successful career in technology, writing books, and growing a business, Jeffrey Ton suddenly found himself stepping away from work to become a full-time caregiver for his wife following a devastating diagnosis.

In this episode, Jeff shares how revisiting memories of traveling the Lewis and Clark Trail with his wife helped him process grief, rediscover meaning, and reconnect with the person she has always been beyond her illness.

Their journey became the foundation for his newest book, Uncharted Moments: Love, Legacy, and the Lewis & Clark Trail.

In this episode, we covered:

• Why becoming a caregiver forced Jeff to let go of a business and identity he loved
  
  
• What anticipatory grief taught him about navigating uncertainty and change
  
  
• The remarkable story behind retracing the Lewis and Clark Trail together
  
  
• How slowing down changed the way Jeff and his wife experienced life
  
  
• The powerful lesson Jeff learned about pausing during chaos
  
  
• How one simple phrase became a philosophy for navigating difficult seasons of life

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Resources

Website: www.JeffreySTon.com


Amazon: Uncharted Moments: Love, Legacy, and the Lewis & Clark Trail by Jeffrey Ton


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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:

rusty@justwalking.com

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