For people who've spent decades succeeding at work, life comes with a scoreboard. There are goals to hit, problems to solve, and clear ways to know when you're succeeding.

Then comes a stage of life when those measurements don't work quite as well. My guest today is psychologist Brent Beam, who works with executives and men navigating major life transitions.

We talk about what happens when the focus shifts from achievement to experience, and why that can require a new way of measuring a good life.

You'll hear about:

• Why Brent encourages men to shift from external KPIs to internal ones
  
  
• How being willing to be bad at something can make life more expansive
  
  
• Why making friends may need to become your new "job"
  
  
• How retirement can put unexpected pressure on a marriage
  
  
• What to consider before assuming a board seat and more golf will be enough

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Resources:

Website: brentbeanphd.com

The How of Happiness by Sonja Lyubomirsky

We spend a lot of time thinking about the past or worrying about the future. What gets lost in between?

For Dr. Evan Fishman, that question became more personal after he was laid off from Facebook in 2023. The experience forced him to rethink how much of his identity was tied to work, achievement, and what came next.

Today, Evan helps others navigate similar questions around identity, uncertainty, and being present.

In this episode, we cover:

• How Evan's Facebook layoff changed the way he saw his life
  
  
• What we use to avoid uncomfortable feelings
  
  
• Why fear can create stories that feel true (even when they aren't)
  
  
• How to become more comfortable with uncertainty
  
  
• Why the present moment matters during times of change

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Resources

www.evanfishman.com

https://www.linkedin.com/in/evanfishman

https://www.instagram.com/dr.evanfishman

https://x.com/evan_fishman

https://belovedinstitute.substack.com

The first six months of retirement may be the easy part.

At first, there may be travel, projects, and long-awaited plans to fill the time. But once the dust settles, retirement can begin to feel very different.

Psychotherapist Austin Dowling joins me again on Chapter X to talk about what can surface after the initial transition. We explore loneliness, identity, self-reliance, and the challenge of adjusting habits that may have served us well throughout our careers.

We covered:

• Why loneliness often appears after the first few months of retirement
  
  
• How senior roles can make relationships feel increasingly transactional
  
  
• Why successful people may struggle to ask for help
  
  
• How over-scheduling can become another way to avoid discomfort
  
  
• How to adapt your career strengths instead of leaving them behind

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Resources

Website: www.insighstudiotherapy.com

Email: austindowlingpsychotherapy@gmail.com

Phone: 347-454-2799

We spend decades working toward the exit. But what happens once we actually get there?

Today I'm speaking with Jack Calhoun, who sold his wealth management firm in his fifties expecting to finally relax and write. Instead he found himself restless, then stuck running a company he didn't even like after a bootstrapped venture went sideways.

In this episode, Jack shares what that wrong turn taught him and how it led him to create Encore Career Lab, a program built to help high achievers figure out what comes next.

We cover:

• The moment selling his firm turned from a lottery win into "what have I done?"
  
  
• Why the freedom of retirement gave way to isolation
  
  
• What his coach's "autopsy" exercise taught him about walking away
  
  
• Why ego is the real enemy of reinvention
  
  
• Jack's case for treating your next chapter like a series of sprints (instead of one big bet)

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Resources

Website: encorecareerlab.com

Email: jack@encorecareerlab.com

LinkedIn: https://www.linkedin.com/in/jack-calhoun-encore

We tend to avoid anything we won't be instantly good at. Richard Sparks has spent forty years proving that instinct is wrong.

Richard is a writer who has spent 40 years bouncing between comedy sketches, TV scripts, opera translations, and now fantasy novels. He wrote for a young Rowan Atkinson before anyone knew his name, then somehow ended up translating operas with no background in the form.

In this episode, Richard shares why he never expects a first draft to work and how that same patience helped him build a fantasy series after decades of writing scripts.

We cover:

• The strange side job that taught Richard he could actually get paid to write
  
  
• What happened the first time he watched an actor perform a sketch he wrote
  
  
• The one thing Richard tells every young writer about a bad first draft
  
  
• Why he walked away from decades of scriptwriting for something he'd never done before
  
  
• A story structure mistake he says ruined the ending of a hit TV series
  
  
• The line from Mel Brooks that reframed how Richard thinks about comedy vs. tragedy

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Resources

Get free chapters at: https://richardsparks.com

Creativity isn't reserved for artists. It's something we use every day to solve problems, adapt to change, and discover new possibilities.

That becomes especially important in Chapter X. Retirement reimagines how we spend our time, where we find fulfillment, and what comes next.

Today I'm speaking with James Walters, photographer, podcaster, and author. He shares why curiosity is at the heart of creativity, why success and fulfillment aren't always the same thing, and how a shift in perspective can open the door to new possibilities.

We cover:

• Why James sees creativity as problem-solving in disguise
  
• Why imposter syndrome doesn't retire when you do
  
  
• What it means to rebel against inherited definitions of success
  
  
• Two brothers who waited until their 70s to hike the Appalachian Trail together
  
  
• 3 phases of retirement James has seen in the people he interviews

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Resources

A Joyful Rebellion

Retirement isn't just the end of a career. For many executives, it's the first time they've had to redefine who they are without the title they've spent decades earning.

So why do so many accomplished leaders struggle with this transition? And what can they do now to prepare for what's next?

My guest today is Dr. Kelly Ottman, executive coach, researcher, and founder of Leadership Portals. After interviewing executives before and after retirement, she uncovered surprising patterns about identity, relationships, and the skills people need to thrive in the next chapter.

In this episode, we covered:

• Why the word "retirement" makes executives flinch
  
  
• The surprising skills many leaders find out they're missing after leaving work
  
  
• Why "I'll just join a few boards" isn't as simple as it sounds
  
  
• Losing your prestige vs. losing your credibility (and why they're not the same thing)
  
  
• What Kelly encourages people to create instead of a bucket list
  
  
• What organizations overlook when preparing leaders for retirement

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Resources

Email: KellyOttman@LeadershipPortals.com

Website: LeadershipPortals.com

LinkedIn: linkedin.com/in/kellyottman