
Why midlife is less about slowing down, and more about stepping into purpose, possibility, and financial freedom.
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Chip Conley
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Jean Chatzky
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Chip Conley
The fastest growing set of entrepreneurs in the US is people 50 and older. And it represents like something on the order of 45% of the new businesses that are created in the US are being created by people 50 and older. So for a lot of people, they decide that in this era where they're going to retire from a job they might have had for a long time, they're going to move into something that might have been the dream they've always had.
Jean Chatzky
Hey everyone, I'm Jean Chatzky. Welcome to Her Money. If you've ever wondered what midlife is supposed to look like and why it rarely looks the way we imagine, well, today's episode is for you. We are pulling back the curtain on what it really means to grow older today. Whether you're staring down 50 and feeling uncertain, planning a third act that actually excites you, or just trying to figure out what comes next after a long, demanding career, I promise this conversation is actually going to help. Chip Conley joined me recently on youn Money Map, the show I host for the alliance for Lifetime Income. He is an entrepreneur, bestselling author, and the founder of the Modern Elder Academy, a place where people go to rethink aging, unlock purpose, and reinvent themselves. You might know him from his time helping shape Airbnb or his TED Talk on what he calls the midlife chrysalis. He's here to help us flip the script on aging and show why embracing your next act might be the smartest financial decision you make yet. We're getting into identity, purpose, longevity, and the new rules of retirement. So stay tuned and don't forget to explore the valuable work being done by our friends at the alliance for lifetime income. @protectedincome.org Here is my conversation with Chip. Chip, welcome. Thank you so much for joining me.
Chip Conley
Thank you, Jean. It's great to be here.
Jean Chatzky
It is. It's great to have you. We've actually wanted to get you on this show for a very, very long time. So I'm, I'm glad that you are. I'm glad that you're here. So, as I said, Chip, you've had this very varied career started in hospitality. How did that lead you to what you're doing now?
Chip Conley
As Steve Jobs said in his Stanford commencement speech, it's much easier to connect the dots moving backwards than forwards. And when I look at what I'm doing today, which is a combination of hospitality, a retreat center environment, and I was on the board of the most famous retreat center in the US called the Esalen Institute in Big Sur, California, for 10 years, wellness, and I own the largest spa in San Francisco. And then this education around midlife, which I learned at Airbnb and wrote a book called Wisdom at Work, the Making of a Modern Elder. So it's those four components, hospitality, retreat center, wellness, and midlife education. So I can look back at my past and say, yes, I see. This is the crescendo. And at the same time, if you'd told me, I, I don't know, 15 years ago that I would be a midlife activist and living in Mexico part time in our campus there in Santa Fe, New Mexico, the rest of the time, I would have laughed at you. So sometimes things just sneak up on you. And I love this primarily because I think midlife is the Rodney Dangerfield of life stages. It don't get no respect.
Jean Chatzky
I imagine that that's a good part of the wisdom that you impart at Modern Elder Academy, that some, sometimes life happens. And if you can allow yourself to walk through the doors that open, you may find yourself in a wonderful, wonderful place. Tell us a little bit about this academy and what you do there.
Chip Conley
Yeah, so the origin story really goes back. I'm 64, and it goes back to my gosh, my mid to later forties. I, as you mentioned earlier in my bio, I had started a boutique hotel company. It grew very large, based in San Francisco. And by my late 40s, you know, it had Become Frankenstein. I didn't like it anymore. I, you know, I had 3,500 employees. We were going into the Great Recession, and a bunch of other stuff in my life was not going well either. And so, long story short is I, I ended up having an NDE, a near death experience, and I died nine times over 90 minutes due to an allergic reaction to an antibiotic. And that woke me up at age 47 to say, you know what? I don't have to continue to live my life the way I am. I'm not very happy doing this. And so over the next two years, up till age 50, I really completely remade my life. But I didn't feel like I had a lot of resources to do that. There were not, there's no midlife wisdom school out there. There was, there were some books on midlife, but they were usually laughable. And I had a best friend who happened to be a coach, and she helped me a lot. But the bottom line was I felt like there's not a lot of resources. And I unfortunately lost five male friends to suicide, ages 42 to 52, during the Great Recession. So I could see that there was a need for this. And then I went into my 50s, and I had the best decade of my life, and I loved it. And I loved being relevant at Airbnb and helping take a little tech startup and turn it into the world's most valuable hospitality company. So in my mid to later 50s, I said, Listen, I mean, why is there not a place for people in the middle of their life? You know, average age of the person who comes to me A is 54. They're in the middle of their life, maybe still have some career ahead of them. They're, you know, a lot fewer and fewer people are thinking about retiring at 60 these days. People are thinking they're going to extend to 65, 70, 75. So why not have this midlife pit stop and create a retreat center dedicated with a curriculum to helping people navigate their transitions of midlife, cultivate their purpose, learn how to own their wisdom, and reframe their relationship with aging. And that's what mea is.
Jean Chatzky
You, I know, had a little trouble with the term modern elder when it was first presented to you, and then you came around to embrace it. So what is, what is a modern elder? How old is a modern elder? What are the hallmarks?
Chip Conley
Well, so Tom Brady was a modern elder in the NFL as a quarterback at age 45. And if you're a software engineer in Silicon Valley at 35, you're probably a modern elder. If you're a fashion model at 30, you might be a modern elder. So it depends on the environment. So the difference between elder and elderly is when they first. The founders of Airbnb first called me the modern elder. I was like, well, screw you. You're making fun of my age. And the truth was I was 52. The average age in the company was 26. So, yes, I was relative to the people around me, I was definitely an elder. But you have to earn the title to be an elder. And a modern elder is not about just like, dispensing wisdom. A modern elder is as curious as they are wise. They are learning as much as they're teaching. And that's what I really did in my seven and a half years at Airbnb. I had to learn. I'd never worked in a tech company before. Yes, I was the mentor to the founders, but I was also reporting to Brian, who was 21 years younger than me, and I was mentoring my boss, in essence, which more and more people are doing, by the way. By the year 2027, the U.S. department of labor says the majority of Americans will have a younger boss. So this is a whole new phenomenon where power is moving to younger people. So modern. To me, modern elder is a term that, you know, some people don't get it until I say it's someone who's as curious as they are wise. And you can be a modern elder at any age. It's not about being elderly the last five or ten years of your life, and it's all about who are you surrounded by? And frankly, how do you fill yourself with curiosity? Because, quite frankly, the people I really admire as they get older are the ones who get more curious and less certain with age. They're more interested in being inquirers.
Jean Chatzky
You made it a goal, a stated goal, to really reframe the way that people think about aging. In your latest book, as I said earlier, you. You write about the fact that midlife isn't a crisis. It's a chrysalis. Right. You're taking us back to what, fourth grade science class?
Chip Conley
Exactly.
Jean Chatzky
Those butterfly gardens that we all I. That we all failed at miserably. I failed at the miserably. So what do you mean?
Chip Conley
I mean the following. There's something called the U curve of happiness, and it shows that actually the low point of adult satisfaction is around 45 to 50. And after that, when you get in your 50s, people get are happier than their 40s, 60s happier than 50s, 70s happier than 60s and women in their 80s happier than 70s. So the bottom line is, yes, midlife can be a crisis, especially around 45 to 50. There's a lot of reasons for that. You can feel just the mashup of sandwich generation. Taking care of parents while taking care of kids. Not much time for yourself. It's when you tend to be the most busy in your life. Bunch of other things too, perimenopause, et cetera. So what's interesting though is that people get happier once they go through this trough around 45 to 50. So in some ways, the way you could look at it is that we're as we're young, in our 20s, 30s and early 40s. We're like the caterpillar who's just eating all the time, bulking up. And we are not eating all the time to say physically. I mean, we're just working all the time. We're on the treadmill and we're optimizing our lives and taking on all kinds of obligations. And then around 45 to 50, we go into the chrysalis. And the chrysalis is a tough time. And for some people, they don't get to the other side very well. And you know, for some of my friends who took their own lives, they didn't get to the other side. And yet in one's 50s, you might be actually emerging from the chrysalis as a butterfly. And the idea that if you're getting happier after 50, maybe things start to look a little more beautiful like a butterfly does. And so that's why, you know, obviously chrysalis and crisis sound very similar. So I like the language, but more importantly, I like the message. And the message is basically this, you're going to go through a challenging time. At some point in midlife, it might be in your early 40s, late 40s, early 50s. That's the most likely scenario in terms of the 12 to 15 years. During that time, you need to have hope and, and have a sense of belief that on the other side of this, things are going to get better for all kinds of reasons. And that's part of what we help teach at mea and that's my book, you know, my book, Learning to Love Midlife. The subtitle says it all, 12 reasons why life Gets Better with Age. And so that the book has 12 chapters, each dedicated to a different thing that gets better with age or a reason that life gets better with age. We know what gets worse with age. You know, our memory, short term memory, our body. Just as we get Comfortable in our own skin, it starts to sag. But it is interesting. There's a bunch of things that get better with age. Emotional intelligence, wisdom, our ability to edit our lives, our understanding of who we are, our spiritual curiosity. The list is 12. There's 12 of them, and they're all based upon social science.
Jean Chatzky
I'm curious about, and I'm so sorry about the loss of your friends that. That must have been. That just horrendous. Awful. But I'm wondering about what differentiates those people who are able to get through with a sense of optimism that there are better things on the other side. I mean, I think I hit my chrysalis at 40. That was the year I got divorced, got fired, lost my father, and turned 40, which at the time I thought was like, oh, my God, 40. And now, right? And now I'm like, okay, so 60. But 60, weirdly.
Chip Conley
You look good. You look good.
Jean Chatzky
Thank you. 60 does not seem as bad as 40 seemed at the time.
Chip Conley
Yeah, well, so there. I think. I think there are a few things. The number one thing I would recommend to anybody going through a lot of difficult transitions is to. Social support's the most important thing you've got. And I would highly recommend this to men in particular, women. Women are so much better at having social support, keeping friendships. You know, they don't have their. Their friendship muscle atrophying. But for a lot of men, they. Because they don't like to be vulnerable, because women are better able to juggle things than men and men are just not as good at socially engaging. These are, again, a gross generalization, but the social science on this is pretty true. What happens is that, you know, at a time when you most need friends, you don't have any around you or you're not willing to communicate about what you're going through. And so, long story short is friendship helps you to, number one, realize that you have love and support in your life no matter what's happening. You go bankrupt, you get divorced. Whatever happens, you have people around you who say, I don't care what happens. You know, I love you just for who you are. There also can be objective. You know, when I was going through my hard time in my late 40s, my best friend was a coach. She was able to be really objective with me and helped me to see that I was. Had a lot of doomsday thinking. Because when you're going through a lot of transitions, you start thinking like, okay, what's going to happen next? It's like, I'm cursed And so having friends can help you to be a little more objective and get out of that dark hole. That's one thing. Another key thing in some kind of downturn like that in your life is to look at how do you take the three stages of any transition, the ending of something, the messy middle, in the beginning. And know that the most important thing to do when you're ending something is to ritualize it in a way that allows you to move on. When you get divorced, you get divorce papers and there's a legal settlement. But the bottom line is no one throws divorce parties. We need to throw divorce parties. You don't have to invite your ex spouse. And then in the messy middle, you just need to be able to see that on the other side of this. Viktor Frankl's book, Man's Search for Meaning, spectacular book about the concentration camps. What he was able to see is the people who got through the concentration camps and got to the other side, psychologically, emotionally, were those who had some hope and meaning that on the other side of this, they're going to be a better person when you get divorced, the pair of glasses you can wear and say, like, I am going to be such a more discerning person in the world when I start dating because I know what I don't want. That's valuable because our painful life lessons are the raw material for our future wisdom. And then finally, last thought is in the beginning stage when you're trying something new for the first time. You know, whether it's dating online or going out and getting a job after having your own business for 15 years or whatever it is, moving to a new place after downsizing. Long story short, is becoming a beginner again, having a growth mindset, having a sense of humor about yourself. Be that butterfly who ends up on the ground as soon as it comes out of the chrysalis because it's got wet wings. It's never flown before, but it has to just learn how to fly. And we need to learn how to try something new and just be terrible at it and then laugh at ourselves, because that's the process of getting better.
Jean Chatzky
Yeah, absolutely. And we're going to take a break. We are back with Chip Conley, entrepreneur, bestselling author and founder of the Modern Elder Academy. So we are, as you know, at our heart, a money show. We are in the midst of what the alliance for Lifetime income calls peak 65. This is the time when more Americans are turning 65 every day than ever before. And our research shows that many of these Folks believe and are at risk of outliving their saving. How do you think that reframing aging can help with these financial anxieties and financial issues?
Chip Conley
Yeah, at MEA we, we sometimes do a whole session on money and our relationship with money and the money script that we were sort of inherited. And one of my favorite questions to ask in, in the classroom when we're doing the workshop is you're going to have a lifetime relationship with money. We all do. If you were to go to relationship counseling with money, what would money say about you and what would you say about money? Because that question sort of brings up this idea of like, what's my relationship with money? And for many people, one of the most important things they need to do as they move into retirement, whether it's partial retirement or full retirement, is to really get conscious about that relationship. The first tendency for a lot of people is to become a bit miserly. Not everybody, but some people because it's like you don't want, you know, it's hard to finance a 30 year retirement with a 40 year career. So if you retire at 65, let's say, and you're going to live till you're 95, oh my gosh, how are you going to do that? And especially with the inflation we had the last couple years. So the key thing is to really understand what is it that is most important to you. For a lot of people, what's meaningful to them as they get older is not material things. It may be that the material things are the things that really gave them a sense of status and was something that they could provide for their family. But maybe, you know, you're empty nesters now. Maybe you're actually living alone, your partner spouse has passed away or they, you guys have gotten divorced and you're sort of in a place where you have a lot more options to end agency in how you want to spend your money. I'm a big fan of people considering being an expat. And I don't think it's, you have to do it year round. You know, I live in Baja part time in Mexico, which an hour north of Cabos and Lucas. It's got all the health, it's got great healthcare, it's the cost of living is one third of what it is in the United States. There's no keeping up with the Joneses and all of the sort of like conscious materialism that you can sometimes see in some places in the U.S. it also more than just your spending coming down, it also allows you to become a beginner. I mean, I started learning Spanish at age 56, which was in my mind a little bit too old to learn a foreign language. But when I asked the question 10 years from now, what will I regret if I don't learn it or do it now, living in Mexico part time, you know, I said, like, hey, at 56, it's going to be easier to learn Spanish than at 66, 10 years from now.
Jean Chatzky
True.
Chip Conley
So there's a lot of opportunities to sort of feel like a beginner again when you're an expat. And that's one way to save money. Another thing is like, you know, for a lot of people, having a portfolio career where you have a bunch of different ways of making money, Obviously I have an affection for Airbnb. But you know what was so interesting in Airbnb is so many of our hosts globally were people who were in semi retirement or retirement and they had extra space and this was became part of the retirement income. So renting your place, renting your second your a second home, renting a bedroom down the hall or a cottage in the backyard, doing some consulting work in the area that you've always been interested in. I have a friend who always wanted to be a baker, and so she started doing baked goods and she was a lawyer and started doing baked goods on the side. Ultimately, she. She became a baker and entrepreneur, but for a year or so there she was just like making, I don't know, made 10 to $20,000 a year just on the side doing baked goods. And she built a whole online presence on it, and it was something she loved. So combining what you love with something that can make you some money is a way to move into retirement in a new way. Because the math that we've used historically on retirement has some flaws in it. It assumes people are going to die earlier than they probably are. It assumes they're going to stop making money earlier than they are. And so that's really. We should assume that for the future we're going to live longer and we're probably going to work longer, whether it's full time or part time.
Jean Chatzky
Wait, talk a little bit more about both of those things because I think there is a lot of myth busting that needs to be done where we're sort of both longevity and this I'm going to retire and never earn a cent ever again attitude. It's just not true anymore.
Chip Conley
No, it is not. Well, let's do some longevity literacy for a second, which is, number one, is if you are 60. I'm 65 later this year. So I am, I am your customer. So I, if I look at, let's say I'm 65, if I look at the actuarial tables and see that the average American male lives till 76, I would think I have just 11 years left in my life. But the truth is, the math is interesting. Once you've gotten to 65 as an American male, you're likely to live to 82. So instead of dying in 11 years, you die in 17 years. So you have, you have one third more or actually 50% more than you thought you had in terms of life left just because you've already lived to 65.
Jean Chatzky
Well, and, and every year your longevity goes up. I mean, this is where people get it wrong, right? The longer you live, the longer you are probably going to live. And that is just, there's that and.
Chip Conley
There'S also the data. Guess what? If it's saying that the average American male lives till 76, this is based upon people who've already died then. So this is based upon, okay, 76 years ago was 1949. This is based upon, you know, people who have lived from 1949 till 2025 and they're 76. What about I'm, I was born in 1960. Longevity has been going up over time. So the longevity for someone who's a 1960 baby is higher than someone who was a 1949 baby.
Jean Chatzky
Right?
Chip Conley
And then add a third factor here around longevity, literacy. And that is that we are much smarter about our health today than we were 50 years ago. Whether it's drinking, smoking, it doesn't mean we don't have more death by despair. And we do. I mean, and actually longevity in the US is 48th in the world. So nothing to be proud of, to be honest with you. So that's one piece. The other piece is that the working longer. And that one's sort of obvious in a world in which 50 or 75 years ago most workers were doing back breaking or mind numbing work. By the time you get to 60, you wanted to go to Sun City, you wanted to hang out on a golf course, have a martini at lunch and play bingo in the afternoon or take a nap. And that was partly because you had spent your body. But you know, today there are over a billion knowledge workers in the world. And so the people who are, you know, who are often thinking about these things are people who have been using their mind. And so the idea that at 60 or 65 you're going to Turn your mind off. And right at the point where all your wisdom is even more valuable. That doesn't make sense. And so maybe you're going to move out of a full time role. Maybe you're going to move out of a role where you have a singular job, one paycheck and nothing else. Maybe you're moving into something that's part time. Maybe you have built an investment portfolio and you can live off of some of the investments you've made as well. So I mean people have a much more active point of view about what it means to be in their 60s, 70s and 80s today compared to my parents generation.
Jean Chatzky
I've heard you say that those knowledge workers, and I'm one of them. So I again feel like a poster child are having a harder time with the whole concept of retirement than other people.
Chip Conley
I mean this is true. Having had over 7,000 graduates come through our MEA program from 60 countries. It's also true across countries that I the word retirement sort of makes some people feel very awkward. They don't like it. Now some people do, I don't. Especially if you're, if you are working in the military or in the government and you. Part of the reason you went to work there was job security and great pension and early retirement. You're like, yeah, I'm going to take off at age 55 or even 50. But those people, that fireman who's actually grad or who's retiring at age 50 decides that he wants to go sport fishing and he's going to buy a boat and he's going to have a sport fishing company. You know, the fastest growing set of entrepreneurs in the US is people 50 and older. And it represents like something on the order of 45% of the new businesses that are created in the US are being created by people 50 and older. So for a lot of people, they decide that in this era where they're going to retire from a job they might have had for a long time, they're going to move into something that might have been the dream they've always had. And so yes, people are going to be in the workplace longer. And let me say one last thing. The demographics are going to require this because we have a big challenge in the US less so than Europe, less so than Asia, but we're not hitting a replacement rate. If we didn't have immigrants in the United States, we would not actually be anywhere close to the replacement rate because we're. The replacement rate means 2.1 kids per, per woman, a childbearing woman in the country. And bottom line is we're below that. And therefore we are going to have less people coming into the workplace than we have historically had. And by, by that fact, we're going to have a very low unemployment rate and there's going to be a need for people to stay in the workplace longer. And employers are going to get smart after having been ageist for many years. They're going to realize, okay, this is not about trying to get rid of people over 60 in the company. This is actually how do we keep our people over 60 because we need to have some stability in the business. I wrote a book called Wisdom at Work, which is about intergenerational collaboration in the workplace. And you don't want to have to be in a position where we have a lot of positions in the company open because you can't fill them with young people.
Jean Chatzky
At a time in our lives, in our world where we get research after research after research that shows that a lot of people are unsure about what comes next, purpose wise, financially. These are people in their 50s mostly. What three pieces of advice would you give them as we wrap this up? And also which ones of them should head to New Mexico or Baja? For me A.
Chip Conley
Well, I think that if you're going through a transition, the number one reason people come to me a and we have online programs too. So it's not. They don't have. A person doesn't have to come to one of our campuses. There's lots of wonderful online programs we have and we have 56 regional chapters around the world. So once you become an alumni, you're part of the whole community. People tend to come to MEA because they're going through a transition. But I would say three pieces of advice would be beyond doing something. With me, a number one is get conscious about your money script. As I said earlier, really understand whether you are living the script your parents gave you or that your community gave you or your spouse gave you. Is that your script? Is that really is. Is this relationship? You know, do you want to be a miser about money? Do you want to be on the opposite end, which is like just connoisseur diva, spending money left and right. Being conscious about something allows you to have some control over it. So that's what number one, number two is. Do know that retirement accelerates mortality by two years. And so not having a purpose doesn't. Your purpose doesn't have to be career. It could be a being a grandparent, it could be being a political activist, whatever. It is it doesn't have to be making money, but having some level of purpose associated with how you're living your life is really important. And so do know that when you're retiring from something, you should be retiring to something, meaning you're moving into something new. And then I would say number three is look at the idea that experiences are more important than material things. Because one of the biggest challenges for people is they say they want to keep up their lifestyle in retirement or their financial advisor says, well, you can keep up 70% of your lifestyle. And I think the question, it sort of goes back to the money script thing. Don't think that your default lifestyle you've had is necessarily the lifestyle you have to have moving forward. And whether that means becoming an expat or it means, you know, moving from that five bedroom ranch home with that all of the kids lived in and you're now going to downsize to something and live in, live in town in a two bedroom condo and you're going to be happy about it because you just put a million dollars in your pocket from the difference between what the ranch home sold for versus what you bought the condo for. You know what, there's lots of freedom. A lot more. You have more, more options than you know.
Jean Chatzky
You just described my life and I can walk everywhere I want to go. Which is, which is good for you. Which is, which is good. Fantastic. Chip Connolly, you were worth the wait. Thank you so much for being here with people. Want more on mea. Where do they go?
Chip Conley
Meawisdom.com and you'll find there. I have a weekly podcast. You'll see that in the free wisdom section. I also have a daily blog. You'll see that as well. That's the best place to find us.
Jean Chatzky
Thank you so much for doing this with us today. If you're looking for more tools and information to help you make the most of your midlife and retirement, you can visit us at the alliance for Lifetime income's website@protectedincome.org and please take time to sign up for our newsletter while you're there. It's protectedincome.org subscribe. Thank you Chip. Thank you everybody. We'll see you next time. If you love today's episode, please take a moment to leave us a five star review on Apple Podcasts. Your feedback means the world to me. And if you're ready to keep the Money conversation going, HerMoney has three amazing programs designed to help you feel more confident and in control of your money. There's Finance Fix. It's our four week coaching program that helps you rethink your spending, find hidden savings and make sense smarter choices for the future. Our pre Retirement program runs for six weeks and walks you through building a retirement strategy that's personalized for your next chapter. Finally, there's Investing Fix, our investing club for women. It meets every other week on Zoom. It is a supportive space to learn, ask questions, grow your your investing confidence and build your portfolio. And your first month is absolutely free. These programs are truly helping level the playing field for women financially. I'd love for you to join us. Her money is produced by Haley Pascalides and our music is provided by Video Helper. Thanks so much for listening and we'll talk soon. Hey, I'm Dr. Maya Shankar. I host a podcast called A Slight Change of Plans that combines behavioral science and storytelling to help us navigate the big changes in our lives. I get so choked up because I feel like your show and the conversations are what the world needs. Encouraging, empowering counter programming that acts like a lighthouse when the world feels dark. Listen to A Slight Change of Plans wherever you get your podcasts.
HerMoney with Jean Chatzky
Episode: Your Money Map Replay: How Midlife Can Be Your Most Meaningful Chapter
Host: Jean Chatzky
Guest: Chip Conley, Entrepreneur, Bestselling Author, Founder of the Modern Elder Academy
Release Date: July 25, 2025
In this empowering episode of HerMoney, Jean Chatzky delves into the transformative journey of midlife with special guest Chip Conley. As the founder of the Modern Elder Academy (MEA) and a seasoned entrepreneur, Chip offers valuable insights into redefining aging, finding purpose, and navigating the unique financial challenges faced during midlife.
Background and Career Evolution
Chip Conley shares his diverse career trajectory, emphasizing how his experiences in hospitality, wellness, and education have culminated in his current role at MEA.
"When I look at what I'm doing today... it's a combination of hospitality, a retreat center environment, wellness, and midlife education." (03:22)
Founding the Modern Elder Academy
Triggered by a near-death experience (NDE) at age 47 and the loss of five male friends to suicide during the Great Recession, Conley recognized the scarcity of resources addressing midlife challenges. This realization led to the creation of MEA, a retreat center dedicated to helping individuals navigate midlife transitions, cultivate purpose, and embrace aging.
"We need to have this midlife pit stop and create a retreat center dedicated with a curriculum to helping people navigate their transitions of midlife." (07:14)
Understanding the Term "Modern Elder"
Conley explains that the term "modern elder" transcends age, focusing instead on one's role and environment. A modern elder is someone who is as curious as they are wise, continuously learning and teaching simultaneously.
"A modern elder is not about just like, dispensing wisdom. A modern elder is as curious as they are wise." (07:27)
Earning the Title
It's not solely about age but about the balance of experience and curiosity. Conley cites examples like Tom Brady and seasoned software engineers to illustrate how modern elders contribute uniquely within their fields.
The U-Curve of Happiness
Conley discusses the concept of the U-curve of happiness, highlighting that while adult satisfaction hits a low point around ages 45 to 50, it subsequently rises with each passing decade.
"The bottom line is, yes, midlife can be a crisis... So in some ways, the way you could look at it is... we're going to go through the chrysalis." (09:36)
Chrysalis as Transformation
Drawing parallels to the chrysalis stage in a butterfly's life, Conley portrays midlife as a period of transformation. Though challenging, it offers the potential for greater happiness and personal growth.
"The message is basically this, you're going to go through a challenging time... but on the other side of this, things are going to get better." (09:36)
Social Support as a Pillar
Conley emphasizes the critical role of social support in overcoming midlife challenges, particularly for men who may struggle with vulnerability.
"Social support's the most important thing you've got. And I would highly recommend this to men in particular." (13:08)
Stages of Transition
He breaks down transitions into three stages: ending something, the messy middle, and beginning anew. Ritualizing endings and maintaining hope during the messy middle are essential for positive transformation.
"The most important thing to do when you're ending something is to ritualize it in a way that allows you to move on." (16:30)
Understanding the Psychology of Money in Midlife
Conley discusses how our relationship with money evolves during midlife and retirement, advocating for a conscious approach to financial planning that aligns with personal values and purposes.
"Understand whether you are living the script your parents gave you or that your community gave you." (17:14)
Strategies for Financial Stability
Conley suggests practical approaches such as becoming an expat to reduce living costs, embracing a portfolio career, and leveraging platforms like Airbnb for additional income streams.
"Combining what you love with something that can make you some money is a way to move into retirement in a new way." (19:56)
Longevity Literacy
Conley highlights the importance of understanding modern longevity trends, noting that people are living longer and healthier lives than previous generations.
"Once you've gotten to 65 as an American male, you're likely to live to 82. So instead of dying in 11 years, you die in 17 years." (22:32)
Shifting Retirement Paradigms
He challenges the traditional notion of retirement, advocating for continued engagement in meaningful work and embracing longer, more active careers.
"People have a much more active point of view about what it means to be in their 60s, 70s and 80s today compared to my parents' generation." (24:53)
Economic Demographics
Conley touches on the demographic shifts necessitating longer workforce participation, emphasizing the need for intergenerational collaboration and reducing ageism in the workplace.
"By the year 2027, the U.S. department of labor says the majority of Americans will have a younger boss." (07:27)
Three Key Pieces of Advice
As the conversation concludes, Conley offers actionable advice for individuals navigating midlife transitions:
Conscious Money Script
Purpose Beyond Career
Prioritizing Experiences Over Materialism
Embracing New Lifestyles
Conley encourages embracing new lifestyles that prioritize financial freedom and personal fulfillment, such as downsizing or relocating to cost-effective regions like Baja, Mexico.
"Don't think that your default lifestyle you've had is necessarily the lifestyle you have to have moving forward." (28:04)
Jean Chatzky wraps up the episode by directing listeners to additional resources for further support:
Modern Elder Academy Resources:
Visit meawisdom.com for online programs, weekly podcasts, and daily blogs.
Alliance for Lifetime Income:
Explore tools and information at protectedincome.org and subscribe to their newsletter.
HerMoney Programs:
"These programs are truly helping level the playing field for women financially." (31:03)
Chip Conley on Connecting the Dots:
"It's much easier to connect the dots moving backwards than forwards." (03:22)
Modern Elder Definition:
"A modern elder is as curious as they are wise. They are learning as much as they're teaching." (07:27)
Midlife as a Chrysalis:
"Midlife can be a crisis... but on the other side of this, things are going to get better." (09:36)
Social Support Importance:
"Social support's the most important thing you've got." (13:08)
Longevity Insights:
"Once you've gotten to 65 as an American male, you're likely to live to 82." (22:32)
Advice on Money Scripts:
"Get conscious about your money script." (28:04)
This episode provides a comprehensive exploration of midlife as a period of profound transformation and opportunity. Chip Conley's insights offer listeners actionable strategies to embrace aging, find purpose, and secure financial well-being during one of life's most meaningful chapters.