Stacy London

Welcome back to Hello Menopause. I'm your host, Stacy London. Today we're flipping the script on what it means to age. My guest is the incomparable Chip Connolly, founder of Modern Elder Academy, bestselling author and former head of global hospitality and strategy at Airbnb. Chip has made it his mission to help people reimagine midlife, not as a crisis, but as a chrysalis, as a time of transformation, purpose and reinvention.

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We discuss what it means to thrive physically, emotionally, and professionally in one's 40s, 50s, 60s, and beyond. We also discuss how we navigate health changes, career pivots, and the ever-present question, what's next? If you've ever felt like a midlife is a messy middle, Chip's here to remind us that it can also be the most meaningful chapter yet. Please welcome Chip Connolly to Hello Menopause.

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Chip Conley (00:00.31)

So let's be clear, like you don't have men on your show very often. So... Yeah.

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Stacy London She/her (00:04.438)

No, we don't have been on the show very often, but that's because Let's Talk Menopause has solely been so far about menopause in terms of the physiological aspects of it. But what we were not really talking about is sort of when you get to chronological menopause, you're also really approaching midlife. And there has been no real roadmap. I think it should be part of social security that everybody go to Modern Elder Academy when they turn 50 because I don't think people recognize, I call it a reckoning to a Renaissance, right? And I know that you feel very strongly about not calling midlife a crisis, but.

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Chip Conley (00:38.785)

Midlife reckoning ball. It's the midlife reckoning ball. Like a wrecking ball.

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Stacy London She/her (00:41.356)

But I feel like we all go through it, man, woman, non-binary, it doesn't matter. We get to this place where we start to question all the things that we sort of held dear in our youth. And for me, that came across first as panic. I don't look like myself, I don't feel like myself, nobody's calling me for my jobs anymore. What do I do? How do I pivot? How do I make this work? And I feel like people go through that in one aspect of their life, if not more, as they're getting to midlife. And was that your experience? Is that how you started midlife? You know, the Modern Elder Academy?

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Chip Conley (01:17.015)

Yeah. So first of all, it's just an honor to be here. And I want to talk about my menopause experience because I did hormone depletion therapy for two years for cancer, prostate cancer. And I literally had all of the symptoms of menopause. So we definitely are going to come back to that. Let me just say that, there's adolescents and there's mid-lessons. We're very familiar with adolescents, although the word was only created in 1904.

And adolescence is loud. It's external. You're doing it in unison with your peers. And there's a social support infrastructure that's helping people. When you go through middle essence, which is the hormonal, emotional, physical, and identity transitions that happen in the middle of one's life, it is not external. It's internal.

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It is not socially supported. There's no real infrastructure. It's subtle and it's not in unison. meaning, it's your menopause can happen over the course of 15 or 20 years or so. Some have kids, some don't. Some people have kids early and some people have kids later. So what I think is really clear here, and I love, I love your framing of the idea of, yes, you're going to get your, your AARP card and an opportunity to go to MEA. We don't really have rights of passage or rituals or schools or tools to help people to make sense of the roadmap of midlife. And the reason, and I'll briefly say the reason I came up with this was because I had a really rough late 40s and never heard of the U curve of happiness which says that yes, 45 to 50 is the hardest time of adult life. And then I entered my 50s and I had a flourishing 50s. I ended up at Airbnb as their modern elder. I didn't love that term, but they said, Chip, a modern elder is someone who's as curious as they are wise and that's what you are. so I was the mentor to the three founders and helping them run the company in many ways. And so long story short, as I...

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I found that my 50s were spectacular and I wasn't expecting that because in many ways we think we're going to go through this big dip around 45 to 50 or whenever it is and then we never come out of it. But in fact we do. And Becca Levy at Yale, I started spending time with her and she showed in her research over 20 years that when you shift your mindset on aging from a negative to a positive, you gain seven and a half years of additional life.

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And so MEA really sprouted out of that. It sprouted out of this, the idea that how do we help people reimagine or repurpose themselves in a social infrastructure context where you are with people and realizing, losing my parents is normal. It's not easy, but it is normal. Being an empty nest, a nester is a normal thing. Getting divorced is not uncommon, losing your job or selling your business or having a cancer diagnosis or going through menopause. These are normal things. So why are we not talking about them more often? That's really how MEA came about. Seven years ago, we have two campuses, one in Baja and one in Santa Fe. And we've had 7,000 people from 60 countries come to our programs and we have 58 regional chapters all over the globe.

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Stacy London She/her (05:04.354)

Wow, wow. First of all, that doesn't even sound like enough for all of us. We need more, we need to replicate all of this. But I'm so curious, I want to go back to what you said before about being the modern elder at Airbnb. That you were this curious and wise founder or co-founder or advisor, any number of those names. But I'm so interested in this because I have felt lately, I'm 55, and one of the things that I keep talking about -

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Chip Conley (05:32.633)

The average age of the person average age of the person who comes to MEA is 54

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Stacy London She/her (05:36.992)

Okay, so this is my time. But the reason that I'm so fascinated by it is because I look at, I've started to kind of ruminate so much about midlife. I love philosophy, so I like big thoughts. And one of the things that keeps coming back for me is that perspective. The first thing you said about perspective, I was like, bingo, because the minute I was like, I'm not going to the gym to lose weight anymore, I'm going to the gym because I need to be as strong as I can so I can walk when I'm 85, is a very different approach to how does everybody look at me as opposed to that internal I want to be strong for myself so I can take care of myself, longevity, all of those things I think that help us change our perspective. The other thing that I find fascinating is that people say, we have an expiration date if we can't make babies anymore as a born female.

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I keep thinking, no, it's that the values that I held in my youth have an expiration date. And now I'm really just pivoting to become more of myself. And so I look at the first half as like, I was acquisitive, really concerned, you know, with external validation. I had to have the house, had to have the car, had to have the, you know, all the things. And now I find myself just yearning to downsize and learn. I'm so inquisitive as opposed to not having this, I used to be the know-it-all in the room and now I'm like, if I'm not the dumbest person in the room, I don't want to be in the room.

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Chip Conley (07:08.485)

That was me at Airbnb. I was, I was brought on to be wise and I felt dumb because I'd never worked in a tech company before. So at 52, I was asking a lot of questions. so there's so much to unpack with what you just said. So the first half of our life, we're accumulating, we can make friends and knowledge and relationships and then marriage and then maybe kids and stuff and obligations and responsibilities. And by the time we hit 50 we are desperately in need of a great midlife edit. The edit meat being yes, it's fine to have some expiration dates on friendships on stuff you own on that sweater that is, you know, two sizes too small. That's fine because pouring out part of your tea out of your cup allows you to pour some hot new tea into the cup. Because the things that are lukewarm in your life are meant to go away. So the process of learning that in our fifties, we can have a new beginning and a curiosity about things and have some time affluence, maybe, you know, we had a lot of time poverty in our twenties, thirties and forties. So what it would be like to actually have some more space in our life so we can actually try some things out.

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Stacy London She/her (08:29.43)

I love that phrase, time affluence.

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Chip Conley (08:31.737)

Time affluence. Yeah, no, it's good. You also talked about the body . And yeah, we move from, you know, our bodies like a rental vehicle we were issued at birth. every one of us, you know, we like at mine today is like Hertz Rental Car. But the rental car that you were issued at birth is, you know, in the early years, you know, up till who knows what age it depends on the person.

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You know, we're shining it, we're making sure it looks good on the outside. And it's really the short-term vanity, which is fine. And then at some point you realize as you suggested that it's really more about the long-term maintenance, not the short-term vanity. And it's about how does it feel like on the inside? And, so, you know, I, the body is a really important piece. you know, it is the, it is the, the vehicle that takes us from one place to the other, but as you get older, it's really more about loving your body and appreciating its role in your life rather than seeing it as an object. And this is, you know, so much more important for women than for men in our culture. partly just because of how we were all brought up. yeah. So, you know, as we get older, your beauty moves from your face to your heart.

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Stacy London She/her (09:52.258)

I love that. But I also think what you're saying is absolutely right. This is a patriarchal kind of culture that we find ourselves in and women are inevitably more concerned, I think, with how they're aging than men generally. But I do think it's interesting because you are the founder of Modern Elder Academy and I'm curious what made you realize in your own life that something like this was going to be necessary for people that the loss or confusion you experienced is certainly universal. But how do you know if you're not talking about it, you know?

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Chip Conley (10:28.921)

Yeah. So the deeper part of my story is from age 26 to age 50, I was running a boutique hotel company that I'd started called Joie de Vivre based in San Francisco. had 52 boutique hotels around California and I loved it till I hated it. And when I hated it, I hated it a lot. And I felt like an identity that was affixed to my body, like, like a bandaid. And there was no way for me to get it off without it being painful.

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And then we had the Great Recession and I was running out of cash and I had an NDE. I died and I went to the other side nine times over 90 minutes because of an allergic reaction to an antibiotic. Unfortunately, there were paramedics when I had my first flatline experience there because I went unconscious after giving a speech on stage in St. Louis. Yeah, I know it's crazy. you know, when you die and go to the other side multiple times and see what's there, you sort of have this weird sense of like, okay.

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Stacy London She/her (11:16.793)

My goodness.

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Chip Conley (11:28.121)

It's gonna be alright. And you know, I don't have to live my life this way. I can pull this bandaid off all over my body and it will be painful. But the identity of being the founder and CEO of the second largest boutique hotel company in the US doesn't have to be my only identity. And over the course of time, I did that. Now, the other thing that happened, Stacy, was I lost five male friends to suicide, ages 42 to 52 during the same time between 2008 and 2010 during the Great Recession. So my own personal experience of like, wow, I could have used a school to help me understand how to navigate transitions in midlife and how to cultivate my purpose, how to reframe my relationship with aging and how to find my wisdom. It was really not until 52 when I joined Airbnb that I realized I even had any wisdom because I was surrounded by people who were half my age. so long story short is, It was the combination of my own personal experience, but also the fact that I lost five male friends to suicide. Now, I also had a lot of women friends who were really struggling with menopause during this time as well. And back then, this was 12 years, 13 years ago, actually more than that. I'm 64 now, so I had my flatline experience when I was 47. So 17 years ago, and these women were like, like no one was talking about menopause and they felt like they're losing their minds. and, so I was also noticing that, you know, I'm a, I'm a gay man. I, you know, I have a lot of female friends. I have a lot of male friends too, but I have a lot of female friends who feel very comfortable talking to me about what they were going through. And I was like, have you talked with your friends about this? And I was like, well, we don't talk about this very much. I was like, okay, like I don't understand, but I think it's time to talk to your friends.

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So it was all of that that led me to the day where I was writing a book called Wisdom at Work, The Making of a Modern Elder, which is my story of being at Airbnb in Baja. When I was in Baja writing the book, I went for a run on the beach and I had a Baja aha. I had a kihne. The epiphany was, you know, why are there no midlife wisdom schools? Why are there no places for people to really reimagine who they are and tap into the wisdom that they've built. Because our painful life lessons are the raw material for our future wisdom. So that's how, that's really how it came about.

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Stacy London She/her (14:04.502)

It's amazing. I'm also curious. I mean, Baja Aja is like the big, you know, breakthrough moment for you. How did you start to assemble? Like, what did it look like when you were that sort of the architecture of modern elder academy? How did you decide what, what to teach in curriculums? Because one thing that I found that I was really stressed, you know, that I stressed out about was that there was this sense of, don't know how to get out of this. I don't know, you could say I didn't walk across the Brooklyn Bridge because I was afraid I was gonna throw myself off of it. I there was real like, I had depression, anxiety, rage, the moods that were so, they almost felt like I had my entire nervous system was deregulated, that I couldn't see the world in any other way than this like particularly negative, very stressful way when I was going through perimenopause.

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Chip Conley (14:53.165)

Yeah, let me answer that in two ways. One is, I think for me in creating the curriculum, I knew that there were things I had learned, but I needed to reach out to experts on midlife and menopause and everything. so whether it was Beck Levy at Yale or Arthur Brooks at Harvard with his book from Strength to Strength, he actually profiles MEA and he really focuses on the

the brain in our career and how the career can make a real big comeback in our fifties. Dacher Keltner at UC Berkeley, who's on our faculty, the world's leading expert on awe was really helpful. Carol Dweck, the mindset expert at Stanford was helpful. So what we did is we tapped into some amazing academics and then we took the social science around midlife and around

the physical side of midlife, but the, the socioeconomic or socio-emotional side of midlife, the cultural, the spiritual side of midlife. And we fused it all together in this curriculum, which is now a five day, five day program in Baja or in Santa Fe. And then we have these online programs as well. and so it was really a combination of evidence-based science along with experiential because the last thing we don't do any PowerPoints, everything needed to be something that could be metaphorical and you know, that could help people to realize that they could be a beginner again. I mean, people learn how to surf down in Baja if they want to, they learn how to ride a horse and do equine assisted learning in Santa Fe if they want to, they learn how to bake bread with a group of people and they learn improv because one of the things that we need to really learn in midlife is how to break out of the fixed mindset that says I'm too old to fill in the blank. Now, the other thing that I wanted to say just about your experience with perimenopause is, I have stage three prostate cancer that spread to my pelvic limbs. And two years ago, a little over two years ago, I had to go through two pretty radical surgeries, ultimately taking the prostate out. 36 radiation sessions and two years of what's called ADT and androgen deprivation therapy. So men go through andropause, but it is nothing like menopause. And it's very subtle. And most, most men have never heard of andropause. But what I went through was menopause because basically they took my testosterone from five 50 down to eight. So my testosterone was just eight for two years. And during which time I had hot flashes, night sweats, emotional ups and downs, brain fog, you know, just all this, you know, all the kinds of things. Now, of course, I didn't have the emotional side of, you know, menstruation . And like the process of like, okay, am I, and the confusion of, know, where am I in this journey of very menopause? I didn't have that piece and I didn't have the history there. didn't have the, you know, birth, the issues around, you know, having children there. So I didn't have any of that, but I had the physical side of it. And I've got to say, I think all men should have to go through it.

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Stacy London She/her (18:20.31)

I don't disagree. I mean, just because there are certain things, same thing, you listen, I wish men could have children because frankly, I don't think there are things that we can completely explain through language, right? Sometimes experience is the only way to feel it. And I mean, it's wonderful to hear you say that one, because I just feel like, yay, we're getting more support in the world, period. But it is also this kind of thing where I do feel like the feminine sort of reproductive journey is one where we're kind of teaching women never to feel safe in their own bodies. And I had this discussion with Latham Thomas, who is a birth doula and also does a lot of maternal care. But she was saying, know, women have never felt safe because we haven't been talked to.

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We've been taught that our period is like, you're a woman, but like, don't stay on the couch. You know, we use words like performance and failure with pregnancy and IVF and things like that. And then, you know, we're like has-beens by the time we get to perimenopause. I mean, we don't get a break. You know, everybody talks about the, what is it, the archetype of women, right? Is the maiden mother and the crone. And I am like, no, no, we are missing the fourth one, which is before the crone, which is enchantress.

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That's where I'm like, I feel more magic in my life and in my thinking than I ever felt as a young person. As a young person, I was much more concerned with what other people thought. I was a lot more narcissistic. And I feel that, now, it's exactly what you said. You learn that part of life, but then the rest of your life is letting go of that. And your identity is much more defined by what you do and… who you are as a person than anything else in the world.

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Chip Conley (20:10.489)

Well, the enchantress speaks to Margaret Mead's language, the cultural anthropologist who called it postmenopausal zest. Postmenopausal zest. And what she said is that it's before crone and is this element of there's a freedom that comes with this. there's a freedom that whether it's people pleasing or whether it's not having to worry about having kids again, it's whether it's, you know, being done with the perimenopause symptoms and challenges. Um, there's something that comes with that . And I see it, you know, 64 % of the people who come to MEA are women. So, uh, as such, you know, spending an awful lot of time with women. Just this last week, I was with Liz Gilbert, uh, and Terry Trent, uh, an amazing thought leader from Zimbabwe leading with me. A workshop of 45 women. And you know, it's just so I learned so much from the women's journey and just the desire and need for women to talk to each other. Now let's also know that men need to do this too. But men are not socialized to do this. You know, for men it's shoulder to shoulder. If you want to actually have a connection and for women, it's face to face. And therefore men.

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When we do workshops that are more men oriented, they are often surfing or mountain biking or, you know, horseback riding, you know, hiking, whatever. I mean, just there's an element of camaraderie and maybe you're at the campfire staring at the campfire talking about something personal. It's harder to do the eye to eye thing for men. but, you know, we all need it. It's, know, the, the, the idea that the number one variable for living a longer, healthier, happier life is pretty conclusive. And it's social connection or what I call social wellness. And if we could think of friendship as a practice, it would help. There's one of my co-founders, Jeff Hamoui, helped teach me this is like, okay, we don't think of friendship as a practice. We don't think about how to improve your capacity to be a good friend.

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And if you were more intentional about it, you'd probably be better at it. And so, you know, I think a really important piece of what it means to get older is learning how to deepen those relationships and be more intentional about them.

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Stacy London She/her (22:45.474)

You know, we talked about this a lot. Just generally speaking in the menopause community is that part of, you know, the whole point of being able to talk about menopause is having this community. And like anything else, I think you require and sort of already have at your command this kind of, you know, understood language with people who are experiencing similar things. It's like a 12 step program. It's like anything else. You understand what you relate to and the idea that you're giving people a space in which to do that. I find it fascinating. is, you know, all the women that I talk to around this age are kind of like done with the, you know, everything's perfect in my life. They're really able to talk about how hard things are. I think there's a lot of issues, particularly right now in this administration. I'm watching women my age get fired left, right and center.

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And I'm also watching them at the top of their careers, their C level. there's just this, we don't know what we're going to do financially. I feel like we are not talking about this idea of retirement as much as intentional communities where we can help.

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Chip Conley (23:53.357)

We have one of those Stacy. we have, you know, one of the things that we saw at MEA, again, it was Jeff who really noticed this. of my co-founders, have two co-founders, Christine and Jeff. And Jeff noticed there were so many people, especially women who after 50 were asking the question. And it's probably because frankly, the dating odds for heterosexual women after age 50 are not very good since 70 % of singles over 50 are women. So what they were asking is how do I live in a community like this? I loved my experience at MEA. I'm gonna come every year, but how could I do this, you know, year round? And so we created a regenerative community, not a retirement community in Baja, about a mile from our campus right near the beach. And it's called Baja Sage. 26 homes around a regenerative farm that sold out overnight. And so we're going to do the same thing in Santa Fe. And yes, it's a thing. I mean, I think, you and I need to hang out and like, you know.

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Stacy London She/her (25:02.53)

We totally do. like, I want to come to Modern Elder Academy. I want to buy property. It's funny, the first time I heard about sort of any intentional living community was Serenby. And one of the things that I find interesting is that at midlife, a couple of things occurred to me. Now I did not have an NDE, but my relationship to mortality changed drastically in midlife. And I think it's, you

one partly what you were saying this idea of like, I'm not using my body just to show it off or party all night or whatever. I'm trying to figure out how to care for her longer, right? But you know, long term value in how strong she is. So, you know, to me, I find that, I find that fascinating, this idea that my perspective changed about that, that my perspective has also changed so much about death, that something that I used to be really afraid of, now that I'm sort of on the back half, I see very differently. I see it as sort of this underline, you these are the parentheses that make the sentence in the parentheses so much more valuable. So my whole attitude towards mortality has changed and my whole attitude towards social contact and friendship, whereas I used to isolate myself when I was sad, now I reach out to people. I want to keep this group together. And we keep talking about the fact that… You know, we need to support each other, whether that might be help financially or help raising your kids or, you know, having a good death. And this idea that, you know, we may keep people alive too long when they're sick. And all of these things that I think change the way we look at life and reframe death as, know, what Ram Dass said, you know, your shoe's a little too tight, you get to take it off. So to me, all the things that you're doing are sort of the things that I believe midlife is really meant to do. And it is this moment where, yes, we are exactly like Margaret Mead, able to do something that is solely about becoming more of ourselves and less about helping everybody else.

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Chip Conley (27:08.025)

Yeah, particularly true for women. know, the idea, you know,

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A lot of men say that the thing that reminds them of what they're supposed to do after 50 is they're supposed to be in service. And that may fit men, but that might not fit women because women have been in service. And for a lot of women, it's not about being in service or I am what survives me. It's more like I am how I find joy every day. And I am here to be a great friend. I'm you know, it's not about caregiving, you know.

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What's been fascinating for me is to study what are the top five issues and worries that men have in midlife versus women. And off the top of my head, I'll just say for men, it's the loss of being virile for men, career and financial disappointment, loneliness, and not knowing what to do with their loneliness. And there's a couple others for men. For women, it's perimenopause, number one on the list and menopause for some is the tyranny of conventional beauty and learning how to break the ties with that, it's, oh, for men it's irrelevant. That's the only one for men. Actually for a lot of straight white men, being over 50 is the first time in their life when they're dealing with an ism. So if you are, it's the first time, because they've never had to deal with racism, sexism, homophobia, et cetera. So suddenly they're like, oh, they're irrelevant. And for women it's invisibility.

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Stacy London She/her (28:35.79)

Yes.

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Chip Conley (28:47.481)

Often romantically and the odds being against them. For women, it's some of the financial challenges because if you actually had kids and were out of the workplace for a while, there's that and you had income that was 80 % of a man's for the same job. And then there's just like the endless caregiving for women. And so it's interesting when we talk about midlife crisis,

almost everybody sort of immediately thinks of the man in the red Porsche with the, you know, trophy girl. So, we don't, but you know, the truth is very men, very few men fit that profile and women don't fit the profile. So, I mean, in some ways, midlife crisis is an innocuous sort of weird Hollywood trope that doesn't really describe. Midlife. I like to think of midlife as a chrysalis.

Not a crisis. A chrysalis is that life stage between caterpillar and butterfly. So it is dark and gooey and solitary. There is an element to midlife, especially 45 to 50, where it's tough and that your perimenopause is tough. Learning to see your body, you know, just as you get comfortable in your own skin, it starts to sag. Tough. So there's an element of toughness, and it's a metamorphosis. What happens in a chrysalis is the magic and there's a transformation that happens. And that's really the opportunity. That's really why I'm a midlife activist. That's why I'm out there telling the world, listen, midlife is a crossroads, but it actually takes you to a better place. And the U curve of happiness research pretty much shows that.

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Stacy London She/her (30:34.048)

Yeah, it's funny. I remember Jodie Foster saying it didn't really hit her till her 60s. And I read an article years ago in Scientific American that said it was actually 45 to 55 lowest point of happiness in a woman's life, specifically around the highest rate of divorce, depression and decreased earning potential, all of which

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First of all, it makes sense to me, and all of which perimenopause could be partly a reason for all of those things. So it was fascinating to me to see that there are, you were saying the difference between men and women and their concerns. So fascinating to me because the ones you were talking about for men, for me, as somebody who didn't get married and didn't have children, those are the things that I'm more worried about than beauty, like irrelevance, financial security, things like that, or I wonder if that's different because I never had a family. It is interesting in letting go of the conventional beauty sense, having been in fashion and style my entire life. I don't know why that was so easy to let go, but it was because I feel like I get the opportunity to reinvent my style identity. Like I got very excited about the process of that and what that looks like in comparison to the fact that I used to wear, you know, skin tight dresses and everything cut down to here and that I don't necessarily need, I don't derive power from that the same way that I used to. And you talked about that a little bit before, this idea of, you women are, you know, you don't get cat called on the street after 50, right? You think you're invisible. I didn't feel that. I felt this incredible surge of power in redefining my look.

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Chip Conley (32:13.303)

You've got a Gloria Steinem look. In all the positives of that, I don't know if that's intentional. I was lucky to interview her last summer at 90. And wow, what a firecracker she is. Yeah, think, you know, the thing that's really true is that, as I mentioned earlier, when we're going through adolescence, we're going in unison with our classmates. I mean, literally.

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Stacy London She/her (32:20.01)

I love her. I will take that.

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Chip Conley (32:41.537)

You're going through first kisses and first, you know, first time driving and all these firsts, but you're doing it exactly the same in the same year with everybody. But as we get older, you know, we have so many different paths we're on that the different paths that we're on allow each of us to get comfortable with the fact that we're not playing the goddamn game of life, which is an American propaganda tool that was meant to say like, there's one path, the old board game, there's one path to living a good, successful life. So being able to have the freedom to, to, you know, be single and to not have kids or to change your career or change your gender or whatever you want to do. There's a lot of freedom. you know, and you care less, you have more, you know, no more fucks left to give. I mean, that's where a lot of it is. that doesn't, you when I say that, it doesn't mean that you don't care about certain things. You just are much more discerning about what to focus and care about and whose opinion matters. And quite frankly, it's a very small number of people about whom you'll feel that way. And what a relief.

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Stacy London She/her (33:54.708)

Exactly. I I felt all of these things. I think when you're talking about the chrysalis period is the period that is difficult for people to recognize at first, something that isn't just tough and sticky and mucky and gross because, you know, all these things start to go wrong. And it is hard. People used to tell me when I first started talking about menopause, stop using scare tactics. And I was like, scare tactics? I'm trying to use prepared tactics.

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Chip Conley (34:21.049)

Find the truth.

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Stacy London She/her (34:22.362)

Right? Yeah, exactly. So, you know, my analogy was like, if you knew that a Mack truck was coming towards you, right? If you knew ahead of time, you'd be able to step out of the way. But if you don't know, you're going to get run over, which is what happens to a lot of people in midlife. They don't expect the reckoning and then they really struggle to see it as a Renaissance. And I'm curious, you know, sort of what, if you could think of three things, maybe physical, emotional, spiritual that need, what is the kind of mind shift that we need to be looking at that you would teach at Modern Elder Academy, what you see coming out of the evolution of Modern Elder Academy, so that people can start to understand a little bit what they might be feeling, right? Because I think self-awareness can get a little pushed out of the way when you're feeling particularly down. And how to stick with it, how to stick with this idea of what's happening is a transformation and not just an ending.

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Chip Conley (35:22.617)

So I with a question that I love asking, um, which is 10 years from now, what will I regret if I don't learn it or do it now? And the reason I love this question is because, um, anticipated regret is a form of wisdom. Um, when you're 20 years old, you don't have anticipated regret. Just like you think you're to live forever, when you're 55 years old, there's certain things that, know, if at 65 Stacy, you're going to regret it. If you don't learn it or do it now. And when I moved to Mexico, uh, eight years ago, nine years ago, I started learning Spanish and, um, learning to surf, even though I was like, I don't know how I was 56 years old. And I was, know, I had a mindset that said I'm too old to do this, but I also thought, God, if I'm going to be in Mexico 10 years from now, I will regret that I didn't start learning Spanish or I didn't learn how to surf.

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Stacy London She/her (36:18.776)

Yes.

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Chip Conley (36:21.047)

So there's an element of the emotional side of this is to realize, yes, you can learn how to become a beginner again. I mean, we learned how to become a beginner over and over again when we were teenagers. And why is it that as we become adults, especially in middle life, that we think somehow we can't learn something new or try something new, et cetera? That's a starting point. I would say when it comes to transitions, almost all transitions fit into three stages, the ending of something, the messy middle, and the beginning of something. And once you know that, and for your listeners, on the MEA website, MEAWISDOM.com is the URL. If you go to the bottom footer, there's something called the Anatomy of a Transition. It's a free ebook, and it helps people understand. click on that and you'll get it. And it says, you start with the ending of something and you want to ritualize that. And then you go to the messy middle and that's when you need social support and you need to understand your through line of what you're going through and how you're going to be better on the other side of this. then the last stage is the beginning of something. And that's when you need a growth mindset. You need to be willing to be yourself, lose your self criticism, be open to trying something new, focus on the improving and then getting better at it.

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Stacy London She/her (37:47.214)

Do you think that that requires, I mean, it requires a certain kind of bravery, I guess, because what we notice right in the elderly, as we get older and older, we become much more rigid. It's funny, I saw it in my grandmother, I see it in my mother now. It's like, don't move things. Like you have to keep pills on the table where they were in that order, or things where we become much more frightened.

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Chip Conley (38:11.577)

Some people do. I would say that's unhealthy aging. That's getting rigid and calcified, including their politics sometimes, where they're just stuck in a certain place. I met my parents, so it's so funny we're talking about this. My parents are 87. I'm in their retirement community now. I had dinner with them and friends last night. And it was really interesting to hear them. And there was a calcification about, you know, athletes getting paid in college for being athletes now. And, you know, in the old days, it wasn't like that. And I was like, I was sort of laughing because it was like, okay, you know, the problem for a lot of us is that if we get very stuck in our thinking in our ways, we are what we wonder why we're so bored. so, so yes, people can get very stuck in their ways as they get older. And that is part of the reason why from a physical perspective, want them to, you want people to do yoga and you want people to go out and do walking because it's really important to be continued to be limber, but it's not just the body. It's the limber of the mind. It's the limber of the mindset and the emotions too. So, I mean, yes. So all of that's true. The other thing is being curious, being going out on an all walk and asking the question before you go out walking it, you know, nature, what do you have to teach me today? Being in awe of the world is really healthy. Good for heart, good for feelings. It calms our nervous system, but it also helps us to see the small part we are in a bigger world, which is really helpful. One of the things that is true is that in our early 50s, people generally speaking, get more curious about the meaning of life and about spirituality and religion. So, you know, as such, you know, how do we stoke that?

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Stacy London She/her (40:58.912)

I think there are so many things that I love bonding on. You when I see people, even on social media, who are Gen Xers, who are like, you know, making fun of what it was like to grow up scrappy and, you know, latchkey kids and all this stuff. There's something about this community I find incredibly satisfying. You know, it kind of ties the events of my life together in a way that does make me feel very much less alone. And, this idea that you were talking about with friendship is another thing that I keep thinking about. We prize romantic relationships just culturally above all else when really to put that kind of pressure on oneself and one other person seems like too much for anybody. And yet, you know, you wonder why kids are into polyamory today. I think it's just because that way everybody's under a lot less pressure. And that's it. What do you think about multi-generational mentorship? Because for everything that you as the, you know, wise and curious advisor of Airbnb gave to the founders, what do you think they taught you?

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Chip Conley (42:15.833)

Listen, I think mutual mentorship, where the mentorship is happening in both directions, that's exactly what I did in my seven and a half years at Airbnb. I was the boomer, they were the millennials, and we learned from each other. We were both better for it. Here's an interesting stat. By the year 2027, two years from now, the majority of Americans will have a younger boss. Now, we've never seen this before. And I think part of what's fascinating is power is moving to younger people faster and faster and yet older people are staying in the workplace longer. So we really do need to learn how to find that wisdom going in both directions, not just from old to young, but from young to old as well. Some of things I learned at Airbnb were I learned a lot about digital intelligence, know, what I call DQ, not IQ or EQ, but DQ. And that really revolved around you know, frankly, how, do you, all of the utility in my iPhone that I didn't even know existed, how to create a website that's sticky and has great UX, how to, you know, how to understand venture capital, a business I didn't understand all that well. So long story short is I, there's a lot to be learned from younger people. And I ended up writing a book about this called wisdom at work, the making of a modern elder that really, that helps people to understand

How do you mentor younger people and how can they mentor you?

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Stacy London She/her (43:47.34)

Yes, yes. And I'm curious that you were saying before that we're more than likely the majority of people in this country will have a younger boss. You know, how do we stay away from that kind of mentality of it's very easy to kind of be a separatist when it comes to generations, right? It's interesting. I see so many commonalities between a Gen X and Gen Z in the fact that just the way that they are breaking down barriers and sort of systemic structures around race, around gender, around sexuality, really allowed, from my perspective, Gen X has a kind of new sense of freedom. They have a new language. Whereas a lot of people used to just say they were gay, they didn't know that they were pan or not even bisexual, just like asexual or whatever it is. They didn't realize that there was another name, a way to specify. So I see kids coming out in their teens and twenties, as much as I do people in their fifties and sixties, that feels like some kind of liberation. That feels like something new. Like there's a, there is a generational connection there that's going to be very powerful.

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Chip Conley (44:55.277)

You know, wisdom, just the topic of wisdom is really interesting. We live in an era in which knowledge, sort of like the end of the knowledge era, because with AI and Google, mean, all the world's knowledge is at your fingertips. It's a commodity. But wisdom, which is really your metabolizing of your life experience to be shared for the common good, wisdom's really valuable and a great balance for AI because it comes from your human experience. Yes, the older you are, the more raw material you have, the more life experience you have. But quite frankly, I know people who are 30 years old who are wiser than 70 year old because they make sense of their life experience. They learn from things and they know. So I just think there's this idea of moving into the wisdom era and wisdom being something that anybody can do. In fact,

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The great thing about younger people learning from their wisdom is the sooner you learn things, the more life you have to take advantage of that learning. When I was 28, I started something called my wisdom book. And every weekend I would spend about 20 minutes writing in my wisdom book a few bullet points of what I'd learned that week and how it was going to serve me in the future. And whether it was personally or professionally or spiritually or physically or relationally, I would make that. And I've been doing this for 36 years. And it just accelerated my cultivation and harvesting of my wisdom. so anybody could do that. And I have taught my leadership teams at Airbnb and MEA and Joie de Vivre, my hotel company, to do that. Where once a quarter the leadership team sits down and says, okay, let's have each of us talk about their biggest lesson of the quarter and how it's going to serve in the future. there's just a, there's a beauty in having people digest and understand what they have learned.

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Stacy London She/her (47:05.71)

I mean, that really is secondary. That does really separate knowledge from wisdom for me, because it's interesting. I gave a speech once at a cosmopolitan summit when I think they thought I was going to talk about the best liquid eyeliner and maybe the best vegan legging, leather leggings. And I wound up talking to these 22-year-old kids who had all just graduated from college about things that I feel like we are starting to lose in a digital environment and the rate at which technology is moving is so fast that this idea of discovery has been lost. And I think that's a little bit sort of maybe the connective tissue between knowledge and wisdom is it's not only experiential for something to happen, you actually have to do something to discover it. Instead of like reading a book about how to do something and then doing it with a certain amount of expectation, this is about doing it and learning without expectation what the lesson is.

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Chip Conley (48:06.361)

That's exactly right. I mean, curiosity and openness to new experiences are variables. They're highly correlated with living a longer, healthier, happier life. And the curiosity about your own life, like, what could I learn from that? How could that serve me in the future? Is something that we're not taught. I mean, in some ways we're taught in weird ways as kids.

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Chip Conley (48:34.595)

Like don't touch the stove. You know, that's a good example. Why do we not keep that process of intentional learning woven into our careers or our relationships or things like that?

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Stacy London She/her (48:37.378)

Right. And I feel this is such good information. One, because people who do get to modern life, to midlife, I don't know in modern times if they're actually aware of the fact that there's so much they don't know, right? Or there's so much that they haven't been taught. I think about things in physical terms too, right? Like, okay, I know how to stay out of danger. you know, if the tide is too strong, you don't go out swimming, those kinds of things. But I think this kind of more...

You know, I'm reading Pima Chodron's We Live How We Die, or I'm paraphrasing, I think. But, you know, I was thinking about the fact that really what that book is about is just being okay with change. Like being okay with the fact that things do not stay the same. And that if you're willing to accept that, if you just have an openness to that, then you really do get the benefit of what, you know, I'm calling sort of this renaissance after all the tough stuff. Because… It's just, I didn't realize how much curiosity plays into being happy at an older age.

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Chip Conley (49:57.379)

Well, curiosity, it goes back to what you're talking about with your mother and curiosity is the opposite of judgment. So, and the, it's sort of the opposite of being stuck. Curious to be curious means you're exploring your options and, and you're learning something new. And so it's, it's, it's an undervalued part of what it means to get older. If you have time affluence, if you have more space in your life you potentially have more time to be curious. Curiosity is not an efficient way of being. And this is why people say, oh, curiosity is great. And then you have a 30 minute meeting with your leadership team to say, let's get curious about this. Like 30 minutes is not enough time. You brainstorm. minutes is not enough time. And so given how busy we are, especially in our 20s, 30s, and 40s, it's understandable why our curiosity muscle starts to atrophy a little.

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Stacy London She/her (50:58.346)

Right. Right. And I think also, you know, we're still working with the same prehistoric software. Well, kids born today who are, you know, were born with screens may have a slightly different brain. I don't know. But, you know, it makes me think about the fact that we are overwhelmed with knowledge. We're overwhelmed with images. We're overwhelmed to the point where our brain really does not know how to process that much information. And, you know, particularly like I see it now with politics, people tell me they can only look at the news once a week or they can't, the onslaught of it is too much, it's too tough. And I really do see that in people in midlife because I think at the same time they're going through this process of who am I now? What do I do now? On top of this kind of, you know, what's going on in the world? How do I remain a responsible citizen? How do I help my community? Things like that. And that...even on that level, I feel like life is changing pretty drastically. And you said it when you were talking about having a younger boss, I think we're going to have five generations in the workforce at the same time. We don't know what that looks like. This idea of finding sea legs and sort of being malleable a little bit to the fact that things don't always go the same way or that things may change feels really important. Like we've got to stay limber mentally.

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Chip Conley (52:17.961)

I mean, we were going through a time of remarkable transition and change. so something we teach at MEA is TQ, Transitional Intelligence. And it's really important because in modern times, we're going through both personal and collective transitions, sometimes voluntary, sometimes involuntary, and knowing how you master and navigate transitions in your life is maybe one of the most important modern skills. And so it's sort of a fundamental and foundational part of our curriculum.

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Stacy London She/her (52:54.056)

My God, I must come visit. I mean, I think I just want to live in Mexico with you, but I'll take what I can get.

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Chip Conley (53:03.033)

Well, just look at the workshop list and then let's talk. We have workshops year round in both Santa Fe and Baja. And then we also have these online courses too.

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Stacy London She/her (53:08.054)

Wonderful!

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Stacy London She/her (53:16.718)

And where do you consistently teach or are you speaking like so much that you're not around?

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Chip Conley (53:21.145)

I teach a lot on both campuses, more on Santa Fe than Baja, but I was literally teaching again with Liz Gilbert last week in Baja. yes, so I do, I both campuses, but we have an amazing faculty and facilitator staff.

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Stacy London She/her (53:38.304)

This is so exciting. Chip, I want to thank you so much for your time. I could not wait to do this interview with you. I feel like you are just this font of knowledge that we need. We're going to need to mine it more and more.

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Chip Conley (53:45.561)

Thank you. If people, if you want to learn more about some of the things I was talking about today on the MEA website, which is MEAWisdom.com, they can, they can see stuff there, but there I have a blog, a daily blog, and it's on the MEA website under free resources or free wisdom. And the one I would just say that people might want to go there and then say, do a little search for midlife crisis for men versus women. And it's a, it's a post I did a year, a couple of years ago that went viral that

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Stacy London She/her (54:14.038)

I love it.

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Chip Conley (54:20.021)

It goes into some more depth on that.

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Stacy London She/her (54:22.648)

Fantastic. Thank you for your time.

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Chip Conley (54:33.401)

Thank you, Stacy.

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