Chapter X with Michael Kay

Transitions are a reality check. There’s never a better time to step back and examine what we really want out of life than during a period of massive change. But you don’t have to wait for a crisis to take stock of your life.

Recently, I came across A Field Guide to a Happy Life: 53 Brief Lessons for Living. It’s an inspiring guide that looks at how we think and what it takes to live our best lives. On today’s episode, I’m joined by the writer of the book. Massimo Pigliucci is an author, blogger, podcaster, as well as the K.D. Irani Professor of Philosophy at the City College of New York. 

His academic work is in evolutionary biology, philosophy of science, the nature of pseudoscience, and practical philosophy. In this episode, he shares why happiness is a process, not an endpoint.

We discussed:

• The journey of Massimo’s midlife career jump from scientist to philosopher
  
  
• Debunking common myths and misconceptions about stoicism 
  
  
• Why everyone has a philosophy of life (even if they don’t know it yet)
  
  
• The concept of training yourself to accept the reality of loss 
  
  
• How to train your brain to stop focusing on what you can’t control

Philosophy as a Way of Life

A Field Guide to a Happy Life: 53 Brief Lessons for Living 

Think Like a Stoic

A Handbook for New Stoics: How to Thrive in a World Out of Your Control

How to Be a Stoic: Using Ancient Philosophy to Live a Modern Life

No matter how much you’ve achieved in the past, entering uncharted territory frightens us all. Coping with change is no simple feat. But what if you could start embracing change by leaning on those around you?

That’s what we explore in today’s episode. Darrell Williams embarked on a path that wasn’t paved with gold or privilege. He forged ahead with an unshakeable outlook of hope, determination, hard work—and the unconditional support of mentors who came before him. 

Today he’s a keynote speaker and master certified life coach. In this episode, Darrell shares his message of getting through change by turning our passions into a new purpose.

• The impact of growing up in a neighborhood plagued by violence 
• Why life-changing mentorship starts with transparency and humility
• How Darrell turned a potentially miserable job into a fun experience
• Taking the risk to surround yourself with leaders who are smarter than you
• The power of collaboration and building an environment of collective success
• Seeing the opportunity of your next chapter to become better than the last

Alliance Seminars Coaching

Today’s guest decided to reinvent himself in the workforce at age 50. After serving as the Chief Financial Officer for a large hedge fund for 25 years, Josh Nadell officially retired in 2019. 

According to Josh, transitioning into his second act started with identifying the most rewarding moments from his previous career. Today he’s a certified leadership coach and the founder of SAGE Leadership Coaching and Development. 

While he’s a little shy of the Chapter X age group, Josh is an excellent role model for growth and developing self-awareness. In this episode, he shares more about the unexpected challenges of transitioning away from traditional employment in the midst of a pandemic. 

We discussed: 

• The key human skills Joshua picked up from working at Goldman Sachs
• Why the journey of learning how to manage people was surprisingly rewarding 
• What the beginning stages of rethinking his career at age 50 looked like
• The struggles of moving on from a career that is your identity and routine
• Pushing the boundaries of your own success (and adopting a new mindset)

http://www.sagelcd.com/

Something that often stops people in their tracks is that feeling that it’s “too late.” Fear tells us that it’s too late to start over; too late to change. As you transition away from work, you might find yourself wondering how to start fresh again.

If that’s the case, I think you’re going to be blown away by today’s guest. It’s an honor to have Gregory David Roberts join us on Chapter X. He’s authored three incredible books (and a new album) that have touched me deeply over the years, including the bestseller Shantaram. 

He is a former drug addict and convicted bank robber who escaped from prison in 1980, spending the next ten years on the run. Once caught, he began serving out a six-year prison sentence, and facing the consequence of his actions became a defining moment. His story is one of growth—trying to separate from one's mistakes to evolve into something bigger, better and more meaningful.

We discussed: 

• How a year imprisoned in solitary confinement led to a journey in self-discovery
  
  
• The unconventional teacher who was the catalyst to jumpstart GDR’s spiritual path
  
  
• Why the destruction of social contracts has created a collective sense of identity loss
  
  
• The significance of finding ways to continue to give after employment ends
  
  
• Two key steps to discovering fulfillment and purpose in Chapter X
  
  
• Why spending time in nature boosts our energy (and reconnects us spiritually)
  
  
• What it means to have an “innocent mind” — and why it matters for inner peace

www.gregorydavidroberts.com

We never know how much time we have left on this earth. Why not do everything we can to make the most of it? That’s how today’s guest approaches each day. 

Norman Sherman worked his way up through the corporate world of advertising to achieve great success. Today he’s semi-retired, not only running his own consulting firm, but also mentoring at SCORE, the nation’s largest network of volunteer business mentors to small businesses.

He is a shining example of generativity, with a willingness to freely share his hard-won wisdom with others in business and life. If you’re feeling hesitant to retire because you’re worried about how to keep your brain engaged, this episode is for you. 

In this interview, we discussed:

• Why a difference in perspective helped him climb the ladder of success
• How Norm’s son helped him rethink the idea of work-life balance
• The unexpected joy of reconnecting with old friends in retirement
• What makes a SCORE mentoring relationship successful
• How learning from younger generations helps him stay curious
• Why travel changed his mind about the strengths of different cultures  

Norman Sherman on LinkedIn

Throughout our careers, we find meaning and external affirmation in the work we do. We’re contained in a reliable groove for the majority of our adult lives, that is until we hit retirement. Today’s guest explains why you might find yourself knocked off your center when that groove falls away.

Jeremy Sherman Ph.D. is a cradle-to-grave researcher – from the chemical origins of life to our grave situation and in between. Not only has he authored over 1,000 articles for Psychology Today, but he has also published two books exploring eight meaty questions about what makes us tick.

As a psycho-protologist, one of the biggest questions Jeremy poses is how we can stop and prevent buttheads without becoming one in the process. Today he shares how he goes back to the origins of life to explain a-holery — and how his unconventional early transition into Chapter X led him to study human behavior.

We discussed: 

• Jeremy’s real-life story of reaching financial security at 16 years old
• How he developed an internal sense of self through self-employment
• A midlife crisis that led Jeremy to discover evolutionary theory
• How to spot assholes—and stop them—without becoming one
• Engaging your curiosity and sense of self in Chapter X
• Jeremy’s advice of designing the constraints in your life

JeremySherman.com

For some men, retirement feels like erasing part of their identity. It causes us to face the big question: who am I, if I am not my job?

Today’s guest shares why retirement isn’t about a loss of self, but a chance to break free from the “autopilot mode” of our midlife and enrich another part of ourselves. As an applied developmental psychologist, Deborah Heiser, Ph.D. has dedicated her life studying human growth and development. 

Not only does she examine the ways we interact with each other, but she also looks at how we adapt to the different seasons of life — from birth until the end. In this episode, Deborah shares with us the power of seeing retirement as an opportunity. 

We covered:

• Why building a social life outside of marriage is essential for older men
  
  
• The commonly overlooked stage of life that motivates us to give back
  
  
• How to practice giving yourself more credit (and why it matters)
  
  
• The reason why retirement makes some people feel a loss of power
  
  
• Reframing the idea that leaving work means erasing a part of yourself
  
  
• 3 surprising things we have to look forward to about growing older 

The Mentor Project

Lee Simonson spent the first 30 years of his career in the radio business and the next 17 as a management consultant. When he realized it was almost time to move on from his career, Lee turned to his wife to figure out their next steps together.

In these conversations, the duo kept circling back to the idea of staying engaged, both mentally and physically, in the next chapter of their lives. That’s when Lee discovered the path of SCORE mentorship.

Today Lee is a full-time volunteer. In today’s episode, he shares his journey of finding meaning in retirement as a certified business mentor. Listen as he explains the types of volunteer opportunities you can find through SCORE — and what he’s discovered along the way.

• How the influence of digital technology changed Lee’s retirement plans
  
  
• The major issues to tackle in retirement conversations with your spouse
  
  
• What SCORE small business mentorship looks like (and who it’s right for)
  
  
• How Lee translates difficult career experiences into teaching moments
  
  
• The biggest challenge that comes with mentoring small business owners
  
  
• Why openness to new experiences can change your life

SCORE

In the past, our success was defined by ambition, taking action, and being high achievers. Shifting from a “work” mindset into retirement isn’t easy. But what if the key to individual growth starts with slowing down and figuring out what matters most?

Joe Jacobi accomplished the rare and spectacular feat of winning an Olympic gold medal, yet he’s achieved even greater heights in the way he helps people live their values. In this episode, he explains the process of acknowledging the obstacles on our journey as a guiding companion. 

We’ll hear thought-provoking lessons from Joe on seeking discomfort, being present, and creating the room to thrive at any stage of life.

Today, we discussed:

• The surprising reward we gain from feeling uncomfortable
• Why participating in a non-Olympics sport benefited Joe’s performance
• The “slower, simple, and less” concept that helps us reflect on life
• Experiencing life transitions and reframing your identity 
• Why Joe chooses to help people through his lived experiences
• His #1 piece of advice for transitioning to new stages of our lives

Joe Jacobi | Performance Coaching

This week on the Chapter X podcast, Richard Eisenberg catches us up on the latest resources and stories from Next Avenue. He will be sharing highlights from recent pieces, in addition to recommending some great book titles for your reading pile.

Next Avenue is the nation’s first and only public media website that serves people in their 50s and 60s to help navigate the second half of their lives. From stories on health to tackling finances and your purpose, you’ll find stories that explore issues big and small. 

In this episode, we take a glimpse into current money matters, timely conversations, and new considerations to make for the next stage.

• The financial experience of Americans 65+ during COVID-19
• 4 key estate planning mistakes entrepreneurs should avoid
• Things to consider when deciding where to live in retirement
• Why you should hold back the urge to over plan your finances

Older Americans Are Getting Slammed Financially During COVID-19 Times

What the Bob Ross Estate Fight Can Teach Business Owners

The Villages Is a Success Story, But Many of Us Want Something Different in a Place to Live as We Get Older

Right Place, Right Time by Ryan Frederick

Health Your Self by Janice Horowitz