Greg Scheinman: An Ode to the Midlife Male

As you reached the second half of your life, you underwent a radical reimagination. The way you describe it is that you went from fat to fit, broke to wealthy, unhappy to fulfilled. What were the triggers that led you to a completely new place in your life?

A lot of people think that I reinvented myself. The reality is, that I didn’t reinvent myself; I released myself.  I think reimagined is also a perfect word. I like that, Michael.

This is always who I was and who I’ve been, and I just didn’t let this out for many years.             

As for the triggers that got me here—and I’m glad you used the plural because I don’t think it’s one thing—I think it’s a series of things that I experienced and learned throughout my 20s, 30s, and 40s that led me to where I am now in my 50s. My father died when I was in my teens, and I spent two years of my 20s as Harvey Weinstein’s assistant, 30 years before the Me Too era. Despite challenges, I went on to produce a couple of moderately successful films. This took me into my 30s when I started a company called Team Baby Entertainment, which I ultimately sold to former Disney CEO Michael Eisner.  During all of this, my brother went to prison. I had a lot of anger and resentment which I masked with a lot of unhealthy behavior. I ended up, in my 40s, going into the insurance business and becoming a partner in a firm, which became my most significant financial success but deepest personal challenge.

One of those significant triggers for change came when I turned 47, the age at which my father passed away. It became a pivotal moment for me, a reminder that life is finite and that I wanted to make the most of the years ahead.

I had spent years chasing all the traditional metrics for success, namely money and entrepreneurship, ego-driven stuff, which left me extremely conflicted. I could never quite figure out where the intersection of personal passion and professional expertise was.  And at the same time, I was trying to be a good husband and father.

I found myself in the parking lot of my office building on my ten-year anniversary at my firm having a breakdown, questioning if the path I was on was truly fulfilling. I had the external markers of success—a partnership in a large firm, entrepreneurial successes, a beautiful family—but when I looked in the mirror, I didn’t like what I saw. It was conformity, complacency, redundancy. I realized I had to make some changes. I didn’t want to repeat the cycle of dysfunction I had seen in my father’s life.  

Another trigger was when my friend’s daughter drew a bottle of Patron on my birthday card. It was a symbol that I was drinking too much, and it was a wake-up call. I had seen the consequences of neglecting one’s health, and I didn’t want history to repeat itself.

You wrote a book called The Midlife Male. What is it about the male experience at 40+ that inspired you to become an author on this topic?

The book The Midlife Male is a culmination of my journey and the lessons I’ve learned along the way. I didn’t initially intend to become an author, but I felt compelled to share my story to help others maximize their lives in middle age. You asked about manifestation and it’s been just that. My breakdown led to me exploring how to change the things in my life that were not working. As I took accountability for my actions and choices, my life got better. We sold our firm which enabled me to start the podcast and ask other men the questions that led me to better conclusions about how I could live and operate better.  The podcast led to my newsletter which helped me to expand my learnings, applying and trying these lessons, which led to a publisher friend of mine saying, “Hey, there’s a book here!” And then it became an Amazon bestseller, which led to more men reaching out and asking if I’d coach them and organizations asking if I’d come out and speak with them.  

The book is all about reframing and redefining success for yourself in midlife, diving deep into the core principles that guided me from dissatisfaction to happiness, health, wealth, and fulfillment in my middle years.         

I emphasize that the middle years are not a decline but a sweet spot, an opportunity to take all that we’ve learned and apply it to lead a better life. I share the five rules I’ve created and live by and my six Fs—family, fitness, finance, food, fashion, and fun—that have become the foundation of success in my own life. The book is a guide for men (and all people, really) who want to make the most of their middle age, challenge conventional notions of aging, and live with purpose. I wanted to write a book that anyone could open at any time to any page and get something of value. It doesn’t have to be read cover to cover.  

The book led to a podcast, speaking engagements, and what you call a High-Performance Lifestyle Coaching Plan. The plan promises to transform an individual or team from mediocre to maximized in business and life. Tell us more about your coaching program.

My coaching program is about helping individuals transform from feeling mediocre to feeling maximized in various aspects of their lives. What I’ve found with most men, including the most successful men, is that there’s always something “missing.” I draw from my experiences and the wisdom I’ve gathered interviewing over 240 high-performing middle-aged men to provide guidance and support. 

We work together to define and design a personalized Midlife Action Plan. It’s a MAP for their life.             

I emphasize the importance of having a plan for life, just as you would for business or other areas. It’s about setting clear goals, being accountable, and following a plan that aligns with your values and priorities. I help men understand that “mediocrity happens by default, maximization happens by design.”

In your coaching program, how do you define success for an individual who works with you?

I don’t impose my definition of success on individuals who work with me. My six Fs don’t have to be yours. Success is a deeply personal concept, and I believe it should be defined by each person. In my coaching program, I guide individuals in discovering what success means to them.

This involves helping them identify their values, passions, and priorities. I emphasize that success should be measurable, quantifiable, and, most importantly, true to the individual’s authentic self. We work together to create a plan that aligns with their unique vision of success, whether it’s in their family life, fitness journey, financial goals, or any other aspect of their life.  Sometimes, guys just want to dress a little better or walk a little taller, and I help them with everything from finding a dentist, trainer, botox, nutritionist, stylist, or therapist. It’s lonely at the top, and men want and need a sounding board, a trusted resource, and a confidante, someone relatable, credible, and even aspirational. 

Now that you are on a journey that views aging as aspirational, how will you continue to manifest that in your everyday life into your 50s, 60s, and beyond? 

My view of aging as aspirational is deeply rooted in my own experiences and the stories of the remarkable men I’ve interviewed. Middle age is a unique opportunity to live longer and better than ever before. It’s not the end; it’s the middle, and it’s where the sweet spot of life truly resides. Despite having to grow up fast in New York, I’m a slow learner and late bloomer.

To continue manifesting this aspirational view of aging in my everyday life into my 50s, 60s, and beyond, I will keep learning and growing. I’ll continue interviewing exceptional men and sharing their stories, inspiring others to embrace the possibilities of middle age.  I’m launching my first group called The Inner Circle in 2024 as well as expanding Midlife Male as an omnichannel media company (with a podcast, newsletter, and monthly magazine) and working to serve the men who need this and the brands that want to reach these men. I will challenge myself with new experiences and goals, both physically and mentally.

It’s about setting new challenges on my calendar, constantly evolving, and following my own Midlife Action Plan. My sons are 17 and 20, and they’re my “why” for everything I do. Aging is not about stagnation; it’s about evolving and thriving. One of my favorite quotes is: “You don’t stop playing because you get old; you get old because you stop playing.”

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