Midlife Male With Greg Scheinman
Posted by John Livesay in podcast | 0 comments


It is often said that midlife is the time when men’s life starts to “die.” But more often than not, it’s actually the time most men really begin to figure life out, and that’s what Greg Scheinman talks about in this episode. Greg is a performance coach and author of Midlife Male, a genuine guide for men to live happier, healthier, and much more fun lives. As Greg always says, if it’s not fun, then we’re done! Tune in and learn all about Greg’s journey in writing the book, how he overcame through the heaviest years, how he received his wake-up call to actually live a better life, and how you can make all of that, too!
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Listen to the podcast here
Midlife Male With Greg Scheinman
Our guest on the show is Greg Scheinman, the author of The Midlife Male. He says, “Show me your calendar and I’ll show you your priorities.” Also, his whole philosophy is, “If it’s not fun, then we’re done,” and finally, how deprivation is not sustainable. Enjoy the episode.
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Our guest is a friend, Greg Scheinman, who is a performance coach, the host of The Midlife Male Podcast and the Creator of Midlife Male, the premier digital media community for middle-aged men seeking to maximize their lives. In 2018, he launched the Midlife Male Movement to help men like him in their 40s and 50s to strive to be their best selves by getting active, curious, naked and real. Greg has played many roles in his life such as a filmmaker, a sports video producer, a TV host, a fitness studio owner, an insurance broker, a performance coach, an executive athlete and most importantly, a friend, father, husband, brother and son. Welcome to the show, Greg.
John, thank you for that introduction. It’s great to be here. I’m like, “Have I done any of that stuff?”
I love to ask my guests their stories of origin. You can go back to your childhood because I know your dad played a big part in your life. You can go back to when you got into fitness or wherever you want to take us to start your story.
I appreciate it. I’ll work backward a little bit. You mentioned my father. One point of origin for me is that my father was 47 when he passed away. One of the things I speak about is that at 47, that’s when my life began. It’s the beginning of what I call the next and best phase of my life. We’re here in early November 2022 and I’ll be 50 in December 2022. It’s been that kind of a journey. You may call me a slow learner or a late bloomer but here we are.
As far as my origin, I was born and raised in Long Island, New York. I was super close to my dad. My parents were great. I’ve got two younger brothers. I had nowhere to go but down, in a way, from where we were raised. We were raised in an upscale, privileged community. It was an interesting way to grow up. I learned a lot as I got older.
Unfortunately, my father passed away when I was 17 and he was 47. I was heading off to college. I was moving to different locations. I went to school in Michigan and Florida. I also spent time in California. I learned a lot. I’m a slow learner and a late bloomer. It was the origin of where my life started. Here we are, where my life has transformed and begun again.
You’ve had quite the journey. I follow you on Instagram. It’s @GregScheinman for anyone who wants to follow you. Congrats on having over 10,000 followers. That’s not an easy feat either. You talked about your son going to college. I was moved by the lessons that you had for him. Since I have more context and texture on your dad dying when you were seventeen, I’m guessing your son was around that age when he went off to college.
I was seventeen and was heading off to school. Our son’s a little bit older. He’s nineteen. He was eighteen when he left for school. It was the same age and the same stage.

The Midlife Male: A No-Bullshit Guide to Living Better, Longer, Happier, Healthier, and Wealthier and Having More Fun in Your 40s and 50s (Which Includes More Sex … and What Guy Doesn’t Want That?)
Were you able to say some things to your son about life lessons that you wished your dad had lived long enough to tell you?
I say way too much to my son. I over-index in that area based on maybe what I’ve gone through. I’m the waterworks guy. I’m a sensitive, vulnerable person. I’m the, “You’re not letting me go. I’m not letting you go,” kind of guy. To me, this is all bonus time so I don’t know how to behave. I didn’t get to see that from the other side. I go on pure emotion and pure heart. I’m like, “The more time I get with you, the more that I can share with you and the more that I could expedite your learning curve, share experiences and maybe save you from the pitfalls, failures and things that I got wrong along the way.”
I also keep thinking about all the things I still haven’t gotten to. Nobody taught me how to play poker and how to tie a tie. It was all the little things. I was like, “Am I covering this? Did I get to that?” I read all these other books about fathers teaching their kids things, life lessons and quotes. That is a long-winded answer to saying, “I throw up all over him.”
In your book, The Midlife Male, one of the six Fs that you have in there is Family. Let’s dive into that a little bit beyond that situation. Do you remember off the top of your head some of those beautiful tips? Whether you’re a man or a woman reading this, I feel that everyone wants to give the people in their life, whether they’re a parent or not, uncle or whomever some life lessons, tips or mentorship. You had so many beautiful ones. Do you remember a couple that you could share of what you wanted? The big takeaway for me from the outside looking in was that you love him unconditionally. In other words, he’s not having to go to college to prove himself to you.
That’s certainly one and I’ll touch on that a little bit. I spent a lot of years chasing authenticity and doing things that maybe you’re supposed to do or you think you’re supposed to do but be successful. You go to college and get a job. You’re supposed to dress a certain way or look a certain way. You’re then supposed to maybe make a certain amount of money. You get married. It seems like there’s a path for men.
In a lot of ways, for men, success is defined as salary and title. Everything else comes secondary, tertiary and so on. I try not to give advice. I’d rather share experiences. Once I changed the framework from viewing success as salary and title, over-indexing in those areas, what was outward facing, whether that was money, car, title, job or house and flipped it inward, it was the more holistic view of success. That is where my success came from. What does success look like to me? It is family, fitness, finance, food, fashion and fun. These are the things I’m into for a variety of different reasons.
You are quite the snazzy dresser. Even your shoes are always on point.
When I say, “People are fashion,” people are like, “What do you mean by fashion?” What I mean there is style and confidence. What makes you feel good? What makes you feel like you? I spent a lot of years in the professional service industry. There was a certain look. It never felt like me in there. It is attributes like that when success went from a one-dimensional approach to a more holistic approach. What does your total life portfolio look like? That’s when everything got better. One of the things I try to talk to both of my boys about is doing what makes them happy and feel fulfilled.
[bctt tweet=”Deprivation is not sustainable.” username=”John_Livesay”]
You were in your 30s when you built this award-winning sports DVD business. It got bought by Michael Eisner who used to run Disney. You are not just theoretically talking about, “Success is empty. For some people, that’s all you have.” You experienced it and therefore realized there’s more to life than just making money.
I’ll give you a story arc. You’re a storyteller. The story arc is everything’s going along fantastic. I’m seventeen years old when my dad passes away. It was the first adversity I’ve ever experienced in my life. I go off to college and go off the rails. I’m like, “Nobody’s watching and controlling me.” In my twenties, I landed my first job as Harvey Weinstein’s assistant right out of college. I thought I wanted to be in the film business. At the time, he was the top of the food chain. My big claim to fame early on was telling Harvey to eff off twenty years before the #MeToo era. I had such a big ego that it never occurred to me that I still couldn’t be successful in the film industry.
I went out, produced a few films and realized that wasn’t a healthy scenario. In my 30s, I get out of entertainment altogether, move to Houston and end up starting this video production company which ends up getting me back into the Hollywood situation by virtue of acquisition and the partnership with Eisner. Once they pull you out, they pull you back in. I realize that wasn’t what I wanted either in terms of entrepreneurship and success. I fell off the rails again.
Many people, whether they had success in multiple industries or they said, “I went to law school. I hate being a lawyer but I feel like I have to stay and do this the rest of my life. I don’t think I can do anything else to make that kind of money,” you are inspiring people in this community you’ve created. It is to say, “It’s never too late to change.” That’s my big observation of what you’re doing.
I’ll keep saying I am a slow learner or a late bloomer. I believe that it’s never too late. We have the opportunity to live again and be healthier, happier, longer, wealthier and stronger than ever before.
Let’s pick up the story again. You’re like, “That is not for me. Working for Harvey was not the thing. Even this DVD thing as an entrepreneur is not the thing. I’m going to do something else.” You have a little bit more tragedy. Somehow, your brother gets put in prison.
My brother was in prison for seven years. With what he did, he was very successful at it. Unfortunately, what he did was not legal. That’s what happened there. There are two things. You lose your life or you lose your freedom. Both of them change the way you see things and they did for me. I didn’t want to squander these opportunities anymore. I didn’t want to squander my life or my freedom, whether that was through a job, not taking care of myself or anything.
Sometimes, these things happen around the occurrence. For me, they happened over a long period to get to a place that maybe should have happened sooner or differently to go, “Haven’t you figured out that you could get sick and die? Haven’t you figured out that you could lose your freedom? Haven’t you figured out that you shouldn’t smoke or drink? How many times do you need to be hit over the head with these lessons before you start to make changes in your lifestyle and show up?”

Midlife Male: Today, we have the opportunity to live healthier, happier, longer, wealthier, and stronger than ever.
That leads to the fitness thing. For those of you who haven’t seen Greg in person or on his website, he is 4% body fat or something amazing. Yet, you also talk that at one point, you struggled with weight, which so many people aren’t going to even fathom. When they see somebody so fit, they go, “He has been fit their whole life. He’s continued that. It’s too late for me. I was never fit so I’m continuing to get worse.” You’re like, “No.”
When I was ten years old, my mom took me shopping to go back to school. She’s like, “I’m sorry. You’re going to have to buy these pants size that is called husky.” I was humiliated. I knew that was a polite word for a fat kid. That image we have of ourselves at ten can carry on. I’m not the only one that gained a lot of weight during the pandemic. I’m like, “This so doesn’t fit anymore.” There is all that stuff. What I love about what you’re doing is you’re helping people not only have financial expertise. The fiscal, you’re combining that with the physical. Those two things go hand in hand a little bit, don’t they?
For me, that bucket that I talked about of family, fitness, finance, food and fashion is all connected. It is what you put on your body, what you put in your body and how you show up. It is the preparation, consistency and accountability. That’s in the gym. That’s outside of the gym. It’s not about having the biggest bank account or being the most jacked.
There is a lot of white space between all of this. It’s about what success looks like for you and what the best version of you is. Aesthetics are a bonus or a benefit of healthy living. It doesn’t mean all that much. I rarely ever get sick and I’ve been sick. I can tell you aesthetics are meaningless. How you feel is everything.
It’s that reminder. What I find fascinating about your framework of the six Fs is that food and fitness are equal. For most people, they think, “If I’m going to be a fitness person. I’m giving up my love of pizza or my love of food, in general, and rich foods.” You’re like, “You can still enjoy food.” That is a very unique take as well. I don’t think I’ve ever seen anybody combine all of these into one framework where you can have all of these things working with you. Probably for someone who tends to eat too fast and not taste the food because they’re eating compulsively or emotionally, that’s what happens. Talk a little bit about how you changed your relationship with food and how you help other people do that.
For one, I love food and my wife loves food. We wish our boys love food as much as we do in terms of an expansive pallet. We’re going to get there. The point being is that deprivation is not sustainable. I talk about it a lot. It’s sustainability, longevity and lifestyle. I don’t particularly care for words like diet deprivation. Supplements are way overused and over-indexed. They’re to supplement things that you’re deficient in. If you’re not deficient, you don’t need supplements, per se, in there. I talk about the use of science in a lot of ways too in terms of getting your blood work done, getting your physicals done and understanding what your body responds well to what it does.
Far too often, we’re jumping on these bandwagons. We’re like, “I should be keto. I should be paleo. I should do intermittent fasting. I should not eat carbs.” We don’t know as far as how we respond to these things. I tend to slant more toward the 80/20 side. I eat clean 80% of the time. By clean, I have foods that are proven for me. I know my body responds well to them. Are they perfect? No. Do I count macros, calories and fat? There is none of that. I’ve got a 30-year body of work.
Here’s the other thing. It is a lifestyle. It’s been good, it’s been bad and it’s been better when you figure stuff. I say that even food is one of the Fs. There is fitness too. Fitness is health. Fitness means a lot of different things. First of all, you got to like it or see if you want to keep doing it. Try different things. Food is the same way. You’ve got to enjoy what you’re eating.
[bctt tweet=”If it’s not fun, then we’re done.” username=”John_Livesay”]
What I’m hearing is that variety is one of your secrets, whether it’s a workout or the kinds of foods you’re eating to keep yourself motivated to keep doing it even.
Fun is one of them too in there. The motto is, “If it’s not fun, then we’re done.” Who wants to eat, day in and day out, things that they do not like? To me, that doesn’t sound like a whole lot of fun no matter what the result is. Often, we look at the outcome and picture. When we look at the meal, people say, “What did you eat?” It’s consistency over time as you’re living a life by design that gets you to maintain, look, feel and perform the way you want.
That is what you mean when you say you are a performance coach. You’re not saying, “I coach athletes to perform in the Olympics.” You’re talking about performing at your best in an obvious situation you’re in, whether it’s work or personal.
That is in life. The way that I coach and work with guys across the country is in all of these areas. It is conceptually about turning these Fs into As. Some guys have a different F. Some guy is like, “I don’t care about the fashion side or the style side of things.” This is not about being on the cover of GQ magazine either. It is about getting dressed, showing up and looking a certain way about how you perceive yourself and how you want others to perceive you. You can wear jeans and a t-shirt every single day. Quite frankly, there’s a right way and a wrong way to do that. If you’re also in shape, eating well and well-groomed, it’s all connected in a way.
I remember once hearing somebody talk about a woman say, “I can never meet any guys on airplanes.” I hear other women meet guys on airplanes. Her girlfriend said to her, “Have you seen what you wear on an airplane? You look like you crawled out of bed.” When I worked at a fashion magazine, we used to say, “Everybody puts on clothes but not everybody gets dressed.”
It’s so true. The old saying used to also be, “Clothes make the man.” It’s not about spending a lot of money. We’ve all seen guys in five-figure suits that look like crap, quite frankly. It’s not about spending. It’s how you carry yourself and put yourself together. It gets back to confidence, pride and a number of these characteristics.
I feel and perform better when I’m dressed a certain way for a certain activity. If I’m going to work out and train, I want to look a certain way because I feel more powerful. I’ll wear a certain pair of shorts, a t-shirt and a pair of shoes. Whatever it is, I want to be geared up for that activity. It’s the same thing in business. If you want to negotiate with me or talk to me about a deal, those calls are scheduled on my calendar after I finish my workout and never before because I feel my strongest then. There is a strategy to these things to design your days.
One part is a surprise for some people. It is fun. You’re like, “Do I have to schedule fun like I scheduled my workout?” I’m guessing I know the answer but I would love to hear you talk about that a little bit.

Midlife Male: Happy and fulfilled people do well in life and everywhere.
One of the rules is, “Show me your calendar and I’ll show you your priorities.” Fun is one of the Fs that I discussed for a while about including it. At the onset, some of the feedback was that fun sounded juvenile. They were like, “Where does fun fit in this area?” Quite frankly, while fun is number six there, you could argue you should flip it around. In a way, it should be right at the top because what are we doing anything in life if we’re not having fun?
For people like you who like to work out, you have fun doing it. For people who hate to work out, it’s drudgery. For people like you who put your family first, you’re going to your son’s game after this interview. That’s not a family first for you but I’m guessing it’s fun for you to watch your son play.
We can all define fun differently in what our priorities are. There’s good fun and there’s maybe not such good fun. I had a lot of not-such-good fun for a lot of years. There was a period in my life when even that worked. My fun is very different. I happen to enjoy working out. I enjoy taking on certain challenges. That is fun for me. I don’t consider that the same level of motivation or discipline because I have a natural gravitation towards that.
In a lot of ways that I work with people, that may not be where they naturally gravitate. They’ve never felt fun before. We have to find things that are fun for them that provide what I call the minimum effective dose. What do you got to put in to get the result you want no more, no less? This isn’t something you truly want to do on your own in there and you go into those areas. Fun is vital. Middle-aged men, in general, are not happy.
There are all kinds of health risks and all kinds of stuff. In addition to people hiring you to coach them and be in your community, you are hired as a keynote speaker. Who hires you? Who’s your ideal audience? What’s your topic?
I learned so much from you about this area because this is a newer part of my journey. When you talk at the onset about it never being too late, I’m getting started in this area. One of my bucket list dream items was to speak on a big stage. Here, you and I are walking around backstage in Detroit and you’re telling me stories. I’m looking at this and it’s amazing.
One, I hope that the takeaway is it’s never too late to do anything. For me, that was writing and speaking. For who hires me and who brings me on, the message is applicable to anyone and everyone regardless of age or stage. I happen to stay narrow and deep in midlife men because that’s where I am.
It’s in the audience’s shoes if that’s whom you’re speaking to.
[bctt tweet=”Midlife does not have to be a crisis.” username=”John_Livesay”]
Some companies and organizations want their people to feel better about themselves and to understand, in a way, that they might not be the CEO of the organization that they work with but they are the CEOs of their lives. They are empowered and able. Quite frankly, if they take care of themselves, prioritize health and fitness, have a personal operating system, watch their sleep and have hobbies and side projects, they’re going to perform better in your organization.
Happy people fulfill people who are good husbands, providers, partners, fathers and parents. These people that are doing well in life do well everywhere. It’s all connected. Those types of organizations hire me because I’ve been on the other side. I have been the entrepreneur who started a company and succeeded. I’ve been the entrepreneur who started a company and failed. I’ve done fifteen years in large-scale professional service companies going from 45 people to 200 people.
I’ve been to every sales meeting imagined. I’ve been to every retreat you can imagine. I’ve had commissions slashed. I’ve had incentive trips and offers. I’ve had speakers up on stage talking to us when we’ve sat there in the audience going, “I can’t believe they paid this guy $30,000 and they got our commission of 20%.” I get it. What motivates you? What drives you?
When we talk about corporate culture, the culture starts with you. Companies don’t care about people. People care about people. Those types of organizations and groups bring me in. These are events, experiences and men’s groups. Women’s groups and organizations, quite frankly, love this because of what they want to know, which is what middle-aged men are thinking. Forty percent of my coaching inquiries come from women. It is not for themselves. They’re like, “Would you work with my husband?”
Speaking of that, that’s what makes this book a wonderful holiday gift for Father’s Day, Christmas, Hanukkah or whatever your thing is around the holidays. What a great gift to give your dad or uncle for Thanksgiving. I’m so grateful to have you in my life as a role model. Your book could not be coming out at a better time. The book is called The Midlife Male. If anybody wants to follow you on social media, they can put that in with your name. Your website is MidlifeMale.com. Do you have any last thoughts or quotes that you want to leave us? Thank you so much for sharing all your passion with us.
This is great. Thank you so much for having me. You touched on a couple of key points. I’ll leave a few takeaways. One is it is never too late. My number one message is to start. People spend a lot of time thinking about when the right time is to start. Whatever that is, whether it’s a health journey, starting a new job, leaving a new job or picking up a hobby, start before it’s perfect. It will never be perfect. Put one foot in front of the other. Get going. You will build momentum. You will ultimately be successful if you are consistent.
The second thing is knowing what’s important is what’s most important. You got to know. I’m going to leave you with another thing. Sit down. Take the time to think about what is most important to you. What are your non-negotiables? What are your priorities? Write them down. Back to the last thing. Back into it. Reverse engineer it. Put it on your calendar. That goes back to, “Show me your calendar and I’ll show you your priorities.” If your calendar is not reflective of what is most important to you in life no matter what your Fs may be, whether it is family, fitness, food, fashion, finance or fun, the numbers don’t lie.
What a treat. I am so excited for people to get this book for themselves and the men in their lives. This is going to be something that people are going to re-read, buy multiple copies of and get people thanking them for giving it to them. You’re a gift. Greg, thanks for giving us your gift of you.
Thank you so much, John. Everyone’s got a story. I appreciate you allowing me to share some of mine. You know how important this stuff is. I appreciate you.
Important Links
- The Midlife Male
- The Midlife Male Podcast
- @GregScheinman – Instagram
- MidlifeMale.com
- https://MidlifeMale.com/About
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Wisdom At Work With Chip Conley
Posted by John Livesay in podcast | 0 comments


When you were young, you had kindergarten. When you were a teenager, you had high school. When you were a young adult, you had college. What happens when you reach midlife? Research says that midlife starts at 35 and ends at 75. Does learning stop at 35? Is that why people call it a midlife crisis? Join your host, John Livesay, and his guest, Chip Conley, in this discussion about why being middle-aged is just bad branding. Chip is the Founder of Modern Elder Academy and is the best-selling author of Wisdom at Work. Learn all about the Modern Elder Academy and why Chip created it to fight off the negative stigma of midlife. Also, learn the difference between retirement and regeneration, diversity, and so much more.
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Listen to the podcast here
Wisdom At Work With Chip Conley
Chip Conley, the Bestselling Author of Wisdom at Work and the Founder of the Modern Elder Academy. He said middle age has bad branding. It’s not just a crisis. We talked about the difference between retirement and regeneration. When you are as curious as you are wise, you are a modern elder. Enjoy the episode. On this episode’s guest is Chip Conley who is a Rebel Hospitality Entrepreneur and New York Times Bestselling Author. He disrupted his favorite industry twice. At 26 years old, he founded Joie de Vivre Hospitality, which transformed an inner-city motel into the second largest boutique hotel brand in America. He sold that after running it as CEO for 24 years.
The young founders of Airbnb asked him to help transform their promising startup into the world’s leading hospitality brand. He served as Airbnb’s head of global hospitality and strategy for four years and now acts as the company’s strategic advisor for hospitality and leadership. His five books have made him a leading authority at the intersection of psychology and business. He was awarded the Most Innovative CEO by the San Francisco Business Times and is the recipient of the hospitalities highest honor, the Pioneer Award. He holds an MBA from Stanford and is also, where we are going to get into, the Founder of something that I’m extremely impressed with called MEA, the Modern Elder Academy.
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Chip, welcome to the show.
John, it’s great to be with you. Thank you.
You have so many words of wisdom. My favorite book of yours, Wisdom at Work is just something I have read multiple times. I usually don’t have the time to read a book more than once but it’s become a resource for me. Before we get into how you’ve got to be so dang smart and wise, let’s go back to your own story of origin. Tell us, childhood or your days at Stanford, wherever you want to start.
I grew up in Southern California in Long Beach. I wanted to be a writer and an entrepreneur and my dad said, “Entrepreneur, yes. Writer, no. Writers are poor and psychotic.” Ultimately, I became an entrepreneur and a writer. I was a rebel, of course, but I went to the College of Stanford. I went to business school at Stanford. I’ve got an MBA. About 2.5 years, out of Stanford Business School at age 26. I decided to call my new boutique hotel company Joie de Vivre. It is not easy to say, spell or even know what it means in America. French for Joie de Vivre. That was our mission. Our mission was to create joy. I figured, “Why not have the name of the company and the mission of the company being the same.”
I started with a broken-down motel in the Tenderloin in San Francisco and grew that into 52 boutique hotels around the State of California over the next 24 years as the Founder and CEO. It became the second-largest boutique hotel here in the US. I loved it until I hated it. There was nothing in between for 22 years. What happened was, I was starting to love the writing more. The third book I wrote was called PEAK: How Great Companies Get Their Mojo from Maslow. It became a bestseller. I started giving speeches on it, and then the Great Recession came along in 2008. I didn’t want to do this anymore. I didn’t want to be founder and CEO anymore but I didn’t set up the company to have a succession plan.
The Great Recession started to wipe us out and I had a bunch of other stuff going on. I had a difficult couple of years around 47, 48, 49 years old. Finally, I’ve got to the places that I’ve got to sell this company. I did it during the recession. What’s fascinating is it allowed me to say, “I now am without a resume, without a job and identity.” It was weird. I felt naked. That’s the time that the three founders of Airbnb came along. A couple of years ago, I joined them and it was a small tech company. Nobody in the company had a hospitality or travel background.
[bctt tweet=”DQ, Digital Intelligence, also requires EQ.” username=”John_Livesay”]
That was a fascinating journey, helping them guide the rocket ship in a 70-hour week. I only did it for four years. While I was there that I came to realize, they were calling me the modern elder behind my back. I wasn’t sure if I liked that. It sounds like modern elder lee. I was mentoring Brian, the CEO and Joe is the Cofounder. He said, “Modern elder’s as curious as they are wise.” That’s what led me to where I am now. When I left my full-time role and became a strategic advisor of the company, it gave me the space to write Wisdom at Work: The Making of a Modern Elder. While I was writing that down here in Baja, where I had a home on the beach, I had a Baja a-ha and epiphany. That’s when I decided, “We’ve got to create MEA.” That’s a quick summation.
There are a couple of things that stood out for me. “I loved it until I hated it.” Twenty-two years, it was joyful. I can’t help but think about personal relationships, marriages, partnerships, or any relationship with something. Not everything has to last forever for it to be a success. We could be in those relationships with ourselves and go, “It’s time for something new.” It doesn’t mean that it wasn’t great or that I’m a failure at this just because I don’t want to do it anymore.
We all evolved and there are things in life that we think will be permanent but nothing is permanent, including ourselves. We die at some point. Your reputation could live on. There’s a famous Developmental Psychologist named Erikson. He says, “I am what survives me.” I like that. It speaks to legacy. Your legacy and your reputation can live on. There are things in life that have to have an end. I didn’t think I would have an end with the company I started but I had a flatline experience. I died multiple times after having an allergic reaction to an antibiotic that I was on. I died on stage, even worse, it was right after giving a speech in St Louis. It was that moment at age 47, almost 48, where I just said, “Something is not working here.” There were a lot of things that are not working. It allowed me to step back and say, “This is the wake-up call for this hotelier.”
I have a phrase that I would love your opinion on, which is, “If not now, when?”
What that phrase does is it says stop procrastinating and stop optimizing for some perfect time because often, the perfect time is now.
The concept of a Modern Elder is as curious as they are wise, I have found that people I know who are fully alive in their ’80s, friend of mine turned 90, she has always been someone extremely curious. That doesn’t stop just because we get older. That need to keep learning and stay on top of what’s going on and have an opinion about something makes me want to dive into what you are doing at the Modern Elder Academy, which is creating, first of all, a safe space for people to be vulnerable. Would you say that’s accurate?

Wisdom At Work: Your legacy and your reputation can live on, but there are things in life that have to have an end.
That is very accurate. This is particularly important for men. Let me give you the background on what it is the Modern Elder Academy and then we can dive into what we do there. While I had this big Baja a-ha reading on the beach, what came to me was the following, why do we not have any schools or tools, rites of passage or rituals for people in midlife? Midlife has a bad brand because we slapped on midlife crisis. That’s the term that everybody associates with midlife.
Sociologists say midlife now extends from 35 to 75. It’s starting earlier than in the past. The past was 45 to 65. Why is it 35 to 75? Why is it a marathon? It’s partly because in certain industries if you are a software engineer, an advertising executive, a model, a professional athlete, there are a lot of industries where people feel over the hill at age 35. Similarly, there are a lot of people who are not going to retire at 65. They are going to live longer. They are going to work longer. If midlife is 40 years long, what do we have to help people through that period? That’s why we created the world’s first midlife wisdom school, the Modern Elder Academy down here in Baja.
Our program is dedicated to what we call long-life learning. We like lifelong learning but long-life learning is a different thing than lifelong. Lifelong learning, says, “At age 30 or 60, you are learning something new.” It doesn’t suggest that maybe what you want to learn and how you learn it is different at age 60 than at age 30. Long-life learning is based on the premise that as we are living longer, we want to live a life that’s as deep and meaningful as it is long. It’s not just about filling your head with knowledge. It’s having the curiosity to figure out what is valuable to you and how can you be a value in the world. How do you cultivate and harvest your wisdom and repurpose it in new ways?
We like to call this same seed, different soil. You have a seed inside of you but the question is, “How do you go out?” Let’s use examples rather than being abstract. My seed was my company. I became one of the better-known hospitality executives in the US as a boutique hotelier. I sold that company. I still had that seed. I thought my seed was exclusively knowing the hospitality business and travel. What I didn’t realize is that seed was wisdom around leadership and entrepreneurship. When I was asked to go to Airbnb, they thought they wanted me for my hospitality knowledge but Brian Chesky has said to me many times, “What we’ve got was not just my hospitality knowledge, we’ve got your leadership and entrepreneurship wisdom.” That’s the same seed, different soil. How do we help people at 45, 55, 65, maybe even 75 take that wisdom, that seed and make it relevant to other people out there in the world?
What you are offering and the success stories that I have seen from being on your email list and watching you on social media is using one of the genres of storytelling that I love, which is this rebirth. It’s a Wonderful Life is an example of a movie that rebirth. Even Prudential at one point had a campaign about your retirement is not a continuation of middle age, it’s your third act. It’s time for a rebirth. That concept, as you said, there’s no transition. Otherwise, it feels like, “I’m in middle age, going to feel and do the same things I have been doing since I’m 40 now that I’m 62.”
That is so helpful to give people, as you said, these same seeds, different soil. For myself, I have looked at it from a standpoint of I have a sales career. I was successful at Condé Nast and other companies. You are like, “What else?” I have given a TEDx Talk. Larry King interviewed me. Now, I have different things to help people with, not just help them win new business. A lot of people have a dream of giving a TEDx Talk.
[bctt tweet=”Midlife has a branding problem.” username=”John_Livesay”]
A lot of people would love to be interviewed by the press. A brand is all storytelling. What story do you tell the press? What story do you tell in a TEDx Talk? It’s a very different story than you speak to an audience of salespeople. Uncovering different parts of our skillsets, in your case, you are like, “I know hospitality.” No, you also know leadership and entrepreneurship. These are things that, especially young people, need and value. You have completely given people a reframing instead of feeling awkward or embarrassed that they are older. You should want this.
There are a couple of thoughts here. Do you know that 40% of Americans have a boss that’s younger than them? If you are 55 years old, 70% of 55 years old have a boss younger than them. By the year 2025, the US Department of Labor predicts that the majority of Americans will have a younger boss. What does that mean? We have never had this. This is a new phenomenon. We never had it before. It’s partly because people are living longer. Sometimes when they get older, they say, “I want to work part-time.” They can’t be the boss anymore. It’s also because of digital intelligence, DQ is more important.
Brian Chesky, CEO of Airbnb and I had a trade relationship. I offered him EQ. He offered me DQ. I was able to offer him some emotional intelligence. When I joined Airbnb, I was 52. Brian was 31. He was my boss. I was his mentor. That’s an unusual situation. What’s beautiful about it is that we had something to teach each other. Here’s your mentorship. Here we have these young digital leaders creating companies that are becoming billion-dollar companies almost overnight and yet they need to microwave their emotional intelligence and leadership skills because they have never been in this situation.
How do we create an alliance between younger and older? These are leaders such that we can be there to support them and help them be better leaders. I’m proud of Brian. I have been working with him for many years. He’s now a public company CEO, Airbnb. Airbnb’s value is worth more than Marriott, Hilton, Hyatt Intercontinental and Wyndham combined, whether it should be worth that to be determined, the fact is what it’s worth. This is a company that has grown to that point. Here’s a guy who went to design school at the Rhode Island School of Design, had no business background at all, and is now leading that company as a public company. Good for him. I’m proud. He’s like my son.
What you are describing, in my opinion, is the EQ that you brought to the table gave him a frame of reference that he didn’t have because he was either too young or it wasn’t part of his skillset yet. Without that frame of reference, you are almost, as a mentor, a Sherpa. “I would climb this mountain before. This is the path we want to avoid. You will get frustrated spinning your wheels here. You need to have this philosophy about hiring and firing people because you will hold on to somebody too long.” It’s not producing whatever the skills that you have been through. You could go, “I don’t have to reinvent every wheel myself. You have been up this mountain before. You can save me so much time.” I love that.
The other thing that I find so fascinating about you is, we both have been interviewed by Ageist Magazine, which you have to be over a certain age and be comfortable with what your age. We are also both openly gay men. I find that everyone has a journey. I think to myself on that journey, two years apart in age, me being 62, the premise of coming out, whenever you do that is one thing. You go, “I’m so much freer than I have this ‘secret.’” Back in the early ’80s, that was not as comfortable to be in the Corporate America world as it is now.

Wisdom At Work: Whenever anyone has to water down or dilute who they are to accommodate the majority, especially the dominant power, they risk losing some diversity and even creativity.
Now, a lot of people feel like they have to keep their age a secret. I thought to myself, “No, you need to come out about your age as well and own that.” Otherwise, you are walking around with another secret. There are few people that I can have this conversation with. Even if you don’t happen to have the coming out of sexuality issue. Many people will be reading this and they are going to be talking about it in terms of whatever age. I feel old over the 35 already. I wanted to bring that up as a topic for you. Even myself, I had to go, “If someone doesn’t want to hire me as a speaker because I’m this age and I’m openly gay, then that’s fine but I’m not going to pretend to be somebody I’m not to get a job.”
I want you to write a wisdom or blog post from a guest post for me on that subject. It’s a great idea. Let’s start by saying, “Whenever anyone has to water down or dilute who they are to accommodate the majority, especially the dominant power or forces, we have a risk of losing some diversity and even some creativity.” This is what I said to the world. We need to have an annual Be the Other Day, BTO because everybody needs to learn what is it like to be in a non-dominant power. It helps people to understand, “I can walk a mile in your shoes.”
I understand if you are a woman in a male-dominant place, an LGBTQ person in a place that’s predominantly heterosexual, a person of color in a place that’s predominantly white, as you said, a person who’s older in a predominantly younger workplace or vice versa. The younger person who feels like they have to almost act like they are five years older than they are, the thing that we need to help people with is the idea that having those diverse voices, there’s so much evidence that diversity on teams on average is better as opposed to worse.
If you are a diverse person on the team but you feel like you have to act like a man, it’s because you are a woman, a white person because you are a black person, a straight person because you are gay, a young person talking as if you rap, that’s 62 years old. That process, if it’s not genuine, if it’s coming from a place of muting who you are, it’s not good for the organization and certainly not good for yourself. I love the idea of coming out with one’s age. It is a very much topic we converse about here at the Modern Elder Academy and especially in our MEA Online class, which is on the website. We definitely go into that topic a lot.
There are six different kinds of ways to engage with the community. One, you mentioned, you don’t even have to go down to Baja. You can connect with the community online. You have these wonderful two weeks or longer sabbaticals. Let’s hear what that’s like.
Sabbatical Sessions was a pandemic project because we had to close down on March 15, 2020, pandemic came along. Six and a half months later, we reopened with what we called Sabbatical Sessions. It’s people coming for extended stays. We have had people come for as long as three months. At a minimum of two weeks, the intent is to give people the space to reflect. The programming we have is much less intense. It’s a little bit each day and it’s all optional. It’s three spectaculars, healthy and delicious meals a day. We are on the beach. We used our campus for a different use, instead of our very intensive, emotionally, physically, intimate workshops, which didn’t feel quite right during COVID. It’s been really popular. There are a lot of people who come for two weeks and say, “I’m staying for 4, 6, 8, then 10.” They keep extending. I hope they don’t have a pet dog at home.
[bctt tweet=”Regeneration, not retirement.” username=”John_Livesay”]
You mentioned that the workshops can be somewhat intense. Who are the workshops for and how would somebody know if that’s something they need?
What we often say is that our purpose as an organization is to help people to navigate midlife transitions. Let’s face it. There are all kinds of transitions that happen in their life. They were not careered once. You have a career or a job transition. You can lose your parents. If you have kids, you can become an empty nester. You could be in the sandwich generation, taking care of your parents and your kids at the same time. You could go through menopause or men go through something called andropause. You could have a divorce or the end of a long-term relationship. There are a lot of things that happen in this period.
A person who is well suited to come to MEA or do the MEA Online course is probably somebody who’s in the midst of transition. A lot of people, with the pandemic, are in the midst of transition. Our workshops here in Baja are based upon the premise that, “You come for a week. There’s a core curriculum that’s 75% of the program of the week. You are in a group of 18 to 20 people. The other 25% is whatever the theme of the week is with the guest faculty member.” The theme could be money, dating and relationships, purpose and legacy, and mindfulness. There are a lot of different kinds of workshops we have, average ages 54. A large percentage of our people here in our Baja campus are on some form of scholarship we give them, which is great. We have a diverse collection of people. Over 60% are women. We want more men. Men have a hard time being vulnerable. A lot of men, not everybody, that’s the program. Now we have bought a ranch, 2,600 acres just outside of Santa Fe. We are working on that campus. Hopefully, we will have a campus in Santa Fe as well.
I know for myself when my dad died years ago and I was still in the throes of working in Corporate America, how intense that was. You had your own health challenges. A lot of us haven’t had that health challenge but when a parent dies, that is a huge wake-up call. I would think a lot of people could use some transition of a wake-up call for your mortality when a parent dies.
Death is one of the things we don’t talk a lot about in our culture and yet it is so inevitable, just like taxes. Helping people to make sense of it, we even have a workshop with Michael Hebb. We started an organization called Death Over Dinner, which is how to have dinner conversations around the subject of aging and death. This guy is in his mid-40s. We are in our late 40s. It’s about around 45 or 50 where people start to think about a little bit more for themselves because of their parents, partly because their own body starts to run down in certain ways. It’s a very important subject. It’s also something you don’t want to be paralleled in Harold and Maude who gets a little obsessed about it. Death is a beautiful organizing principle for life. It helps you to understand how you want to live your own life but it is not the purpose of life. The purpose in life is not dying like the purpose of running a marathon. It isn’t necessarily hitting the finish line. It is having the sense of accomplishment of running 26.2 miles, the enjoyment, and hopefully, the endorphin high along the way.
When I interviewed Alison Levine, the first woman to ever climb Mount Everest, she said, “It’s just ice and rocks gang at the top. That’s not what it’s about.” You think you are going to get there to have some amazing epiphany. The other thing that I’m so impressed with is when someone goes to the Modern Elder Academy, they have the opportunity to be part of this alumni membership. Even if they were not there when some other people who had been there before them might have some wisdom to share, you suddenly are tapping into not just the people you are interacting with when you are there but the entire legacy of all that collective wisdom. It must be an amazing value for people.
When we were doing the beta program three years ago in the first half of 2018 here in Baja, we are trying out MEA to see if people like the idea of the one-week workshops. We used that two-week workshop then. We found that one week was better. The number one thing we heard from our beta participants was, “Where’s your alumni program?” That was a good sign. If the number one question is the alumni program that says, “Whatever we were doing, was working.”
We now have 1,250 alumni from 25 countries who are part of the alumni program. We have twenty regional chapters around the world. The most active one is in Australia and New Zealand. It’s a great collection of people. There are three ways you become an alumnus. You come down to do a workshop here in Baja. We are reopening for workshops until Thanksgiving, do Sabbatical Sessions in the meantime or you do MEA Online, which is the easiest way to become an alum because you do it from home. It’s the most affordable. It’s an eight-week course. That is easy to accomplish and very connected. Most online learning courses are boring and nobody finishes it. We call it digital intimacy. How do we help? You are in a cohort of six people and you feel a sense of digital intimacy by feeling the sense of connection with your small group and your cohort.
You just dropped a really another great value bomb there. I want to underline it for readers, which is when your customers, clients, whatever you want to call them, tell you what they are looking for, that’s your social proof that you should create something. Listen to what people are saying they want or need and would be willing to see value in or pay for. I wanted to underline that. The last thing I want to ask you about is this wonderful pillar of regeneration. You hinted at it in terms of form, soil, seed and putting the same seed in different soil. For their soil, there’s a soul, community and locale. Would you mind touching briefly on that? How can people get a sense of how that would be another compelling reason to integrate that? If one of those is missing, it’s like a stool without enough legs, I’m guessing.
Here’s the idea. In some ways, we are disrupting two industries. Having been a disrupter twice before, I can promise, you become an entrepreneur to be a disruptor. You create something that starts to disrupt. There are two things we are disrupting with MEA. One is higher education. Why are we disrupting or what? How are we disrupting higher education? Clay Christensen, the famous thinker who was unfortunately passed away, said years ago, “Half of the American colleges and universities will go out of business in the next years.”
That was even pre-COVID. COVID has made it even harder more than go out of business. We are disrupting higher education by bringing college professors and academics to the area of long-life learning and midlife learning. What if some of these college campuses that are going to go out of business became a midlife wisdom school? What if alumni can no longer give enough money for a particular campus? It’s gorgeous. It has been around for 120 years. What if that university says, “We are changing our model.”
Instead of dealing with people 25 and younger, we are now in midlife wisdom school. You can get a one-year certificate and you do a gap year. That’s one thing. Secondly, the other thing we have noticed and listened to, is people said, “I love coming to MEA. I want to live this lifestyle year-round, not just one week a year when I come to visit you.” That’s when we started to think, “Let’s create a residential community.” Instead of it being a residential community, we decided for it to be a Regenerative Community, not a retirement community.
[bctt tweet=”Stop procrastinating and stop optimizing for some perfect time because often, the perfect time is now.” username=”John_Livesay”]
What is the Regenerative Community? It has a regenerative farm. It’s better than a sustainable organic farm because it enriches the soil. It does what’s called carbon sequestration, which is good for the climate and has better crops. It’s not monocropping. Instead of a fairway in the center, like in a retirement community, there’s a farm in the center. We have an academy. People come here to learn. If you are in this community and you are buying a home around the farm, you also have a school there. While you may not go to workshops every week, of course, you are not going to do that, there are some collateral benefits to being where the school is.
There’s a famous speaker, Brené Brown is coming to town. She’s going to be giving a workshop for a week, David Brooks, or Paul Hauck. You can sit in on a public lecture that this person is going to do. Plus, other programs as well. Soil is the farm, the soul is the sense of regeneration people have. Community is our broader MEA community, living in an intentional community with a bunch of homes and people who all have similar interests. Locale is wherever we go to do this, we want to be a net positive benefit to the community.
A lot of times, if you think about retirement communities now, they have walled off their gated communities. Everybody there is 65 plus, and often 80 plus. There’s no sense of connection. This is not true of all of them but it’s true for most of them. They are not very connected to the community other than occasionally getting people on a bus and taking them to the shopping mall so they can go shop. Why aren’t there mentorship programs? Why isn’t there a co-working space intergenerationally in the retirement community so that old entrepreneurs and young entrepreneurs can be side by side and learn from each other? Aren’t other volunteers providing service from that retirement community in the broader community? In essence, we are creating a regenerative community. We will be disrupting the retirement community and senior living space. We are disrupting two things at once. Both of them, which is quite frankly ready to be disrupted.
As you are building this regenerative garden, that is a metaphor for people doing the same thing for their body and their mind. Also, the awareness of nature has cycles and seasons, not to resist one coming in the next. There are a lot there I’m sure quite wonderful. Any last thought or a quote from your book that you want to leave us with?
Here are a couple of thoughts. Let me define the word elder. In Modern Elder, they are curious as they are wise. An elder is different from than elderly. Elderly is the last 5 or 10 years of your life. Elder is a relative term. It speaks to who you are surrounded by. If you are an advertising agency and you are 42, you might be an elder. Similarly, if you are a software engineer and you are 40, you might be an elder around a bunch of people who have just joined MIT and know a whole new tech language.
The elder of the past, they were respected because they were perceived as being reverent. There was a revering the elders. You revered your elders. Now is not about reverence, it’s about relevance. The modern elder is not about being reverent to the modern elder, it’s about the modern elder being relevant. That’s why the curiosity piece is so essential. If you are not long-life learning, if you are not constantly learning something new, it’s hard to know how to take that wisdom you have and put it in the context of a bunch of people who don’t understand what you are saying because you don’t understand the tech business as I did. I joined a tech company at age 52, had never been in a tech company. That’s why my curiosity around tech was essential. Otherwise, I would be just passing out wisdom. I was talking about how many rooms a maid cleans in eight hours? That’s relevant to the hospitality industry of hotels but not Airbnb.
If people want to explore being part of that wonderful community, follow you, you have your own website, which is your name, ChipConley.com. Wisdom at Work is the book. Any other ways that you want people to follow you on social media or join your email list?
WisdomWell is one of the better ways. It’s a daily subscriber opportunity that is free. My LinkedIn profile is where we post almost all of those articles so you can stay at it. Keep an eye on it there too.
Chip, thanks for sharing your wisdom, not just at work but in your own life. It has been a joy to interview you.
Thank you, John. I appreciate it. I appreciate what you are doing in the world. You’ve got a great message.
Thanks.
Important Links
- Modern Elder Academy
- WisdomWell
- LinkedIn – Chip Conley
- Wisdom at Work
- Chip Conley
- PEAK: How Great Companies Get their Mojo from Maslow
- Alison Levine – Past episode
- Airbnb
- MEA Online
- Sabbatical Sessions
- Death Over Dinner
- Regenerative Community
- https://www.linkedin.com/pulse/im-coming-out-john-livesay/
- Better Selling Through Storytelling Method Online Course
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