Becoming Modern Elders: From Midlife ‘Crisis’ to ‘Chrysalis’


Episode 245

Chip Conley

In this episode of The Psychedelic Podcast, host Paul F. Austin welcomes Chip Conley, founder of the Modern Elder Academy, to discuss reframing aging and building regenerative communities.

Chip delves into the importance of aging with gratitude in this conversation and shares his journey of creating a midlife wisdom school. Chip also highlights the value of intergenerational collaboration and its impact during his time at Airbnb. He explores how indigenous wisdom influences the academy's approach and discusses how psychedelics can aid in navigating midlife transitions. Finally, Chip shares his vision for regenerative communities, and shares lessons on the ego and the soul that he gleaned from building a boutique hotel chain.

Podcast Highlights

  • The Origin story of the Modern Elder Academy
  • Chip’s role at Airbnb and the value of intergenerational collaboration
  • The Modern Elder Academy: Reframing Aging, Navigating Transitions, Cultivating Purpose, and Owning
  • Wisdom
  • How indigenous wisdom informs MEA’s approach
  • Generativity & the importance of age diversity
  • From 'can-do-it' hero to 'conduit' coach
  • Burning Man, regeneration, and how psychedelics can help with midlif
  • Building regenerative communities
  • Lessons from building a boutique hotel chain

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Podcast Transcript

0:00:00.0 Paul F. Austin: Hey folks, welcome back to the Psychedelic Podcast by Third Wave, where we explore how psychedelics can be integrated into culture for the evolution of humanity. This is your host, Paul F. Austin, and today I'm speaking with Chip Conley, visionary founder of the Modern Elder Academy.

0:00:17.9 Chip Conley: We do not have rites of passage or rituals or schools or tools for people in midlife. There are really four key things to know about the MEA program. Number one is we help people reframe their relationship with aging. When you shift your mindset on aging from a negative to a positive, you gain seven and a half years of additional life based upon all kinds of social science research. So this is a bigger impact in terms of an intervention helping add longevity than if you stop smoking at 50 or you start exercising at 50. So the umbrella for the whole program is how do we help people feel better about getting older?

0:00:52.9 Paul F. Austin: Welcome to the Psychedelic Podcast by Third Wave, audio mycelium, connecting you to the luminaries and thought leaders of the psychedelic renaissance. We bring you illuminating conversations with scientists, therapists, entrepreneurs, coaches, doctors, and shamanic practitioners, exploring how we can best use psychedelic medicine to accelerate personal healing, peak performance, and collective transformation.

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0:04:09.8 Paul F. Austin: Hey, listeners. This is Paul F. Austin, founder and CEO at Third Wave. Today, we have a special treat for you as we dive into the intersections of aging, wisdom, and community building. My guest today is Chip Conley, visionary founder of the Modern Elder Academy, a pioneer in reframing the narrative around aging and how we can cultivate regenerative communities. Chip Conley is on a midlife mission. After disrupting the hospitality industry twice, first as the founder of Joie de Vivre Hospitality, the second largest operator of boutique hotels in the US, and then as Airbnb's head of global hospitality and strategy, Conley co-founded MEA, the Modern Elder Academy, in January 2018 in Baja, California, Mexico. Inspired by his experience of intergenerational mentoring as a modern elder at Airbnb, where his guidance was instrumental to the company's extraordinary transformation from fast-growing startup to the world's most valuable hospitality brand, MEA is the world's first midlife wisdom school and has a campus opening on a 2600-acre regenerative horse ranch in Santa Fe, New Mexico in April 2024. Dedicated to reframing aging, MEA supports students in navigating midlife with a renewed sense of purpose and possibility.

0:05:29.0 Paul F. Austin: A New York Times bestselling author, Conley's seventh book, Learning to Love Midlife, 12 Reasons Why Life Gets Better with Age, is about recontextualizing midlife to help people understand the upside of this often misunderstood life stage. In our conversation, Chip delves into the importance of aging with gratitude and shares his journey of creating the Modern Elder Academy. We get into the value of intergenerational collaboration and explore the impact that collaboration had during Chip's time at Airbnb. We also explore how indigenous wisdom and animism influence the Modern Elder Academy's approach and discuss how psychedelics can aid in navigating midlife transitions. Finally, Chip shares his vision for regenerative communities and shares some of his own lessons on ego and soul that he learned from building a boutique hotel chain. All right, that's it for now, folks. I encourage you to listen to this episode in depth. Check out the Modern Elder Academy. If you want more context on the episode, full show notes, links, and transcripts, you can go to our website to get those. And if you enjoyed this podcast, please share it with a few other folks. All right, without further ado, here's my conversation with Chip Conley. Chip, thanks so much for joining us on the podcast.

0:06:49.8 Chip Conley: Great to be here. Thank you, Paul. I'm coming to you from Santa Fe, New Mexico.

0:06:55.6 Paul F. Austin: How'd you end up in Santa Fe? What was your path and journey to land in such a beautiful, beautiful place?

0:07:03.8 Chip Conley: When I was a kid, we used to come to Santa Fe every summer because my uncle worked for the Navajo Nation. And whenever we got to Santa Fe, I'd say to my folks, like, hey, we're in a different country. And it felt like it, and it still feels like it in certain ways. And as we were growing the Modern Elder Academy MEA, with our first campus being on a beach in Baja, we decided that we wanted a campus in the United States. And Santa Fe felt like the right place for us to create the US's first midlife wisdom school. And yeah, we have a 2600-acre regenerative horse ranch in which the...

0:07:42.3 Paul F. Austin: Wow.

0:07:42.3 Chip Conley: Our campus is just outside of the city limits of Santa Fe.

0:07:48.2 Paul F. Austin: And so why did you look at Santa Fe as a perfect location for Modern Elder Academy? What spoke to you about that location?

0:07:58.4 Chip Conley: Santa Fe has had a long history of being a crossroads for people in the transformational world. And whether it's artists or writers, or it's people taking psychedelics, or those who are, really spiritually inclined, it's been a place and there's a long history of it way before Caucasians were here. I mean, it just has a long history of different peoples coming through here and seeing it as a powerful spot. I love the fact that nature is so plentiful here, because nature is a teacher in our program, and our nature connection and the nature/human connection is an important part of our program. So those are some reasons. It's a place where a lot of people have come to explore themselves and their connection with something bigger than themselves. And there are a lot of great faculty and facilitators here. So it was an easy choice when we were looking at the US.

0:08:57.5 Paul F. Austin: So let's start and open up a little bit about the Modern Elder Academy because I feel like that's really central to what you are doing now. In fact, one of our, someone who I used to work with at Third Wave, Gabrielle Pelicci, recently announced how she had won this writing contest for the Modern Elder Academy. And I was pretty thrilled to see that. So I'd love just to hear a little bit more about the origin story of why Modern Elder Academy, why now, and what to you feels so necessary and important about this initiative.

0:09:33.8 Chip Conley: So my background was for 24 years, I was the CEO and founder of Joie de Vivre, one of the two, one of the really the second largest boutique hotel company in the US based in San Francisco. And I loved it till I hated it. In my late 40s, when I was in the later years after I'd run the company for 20 years, I started not liking it a whole lot. And then my life sort of fell apart in my late 40s as well. And so I got to a place where I didn't wanna do this anymore, but I felt stuck. And I didn't have a whole lot of support. There's like no midlife wisdom school, like an MEA around. And I had a friend who was a coach and she helped me through that time. But everything, everything that could go wrong did go wrong. I sold the company. Ultimately, it's now a Hyatt brand. And then I had my first two years of my 50s where I had some time and space to have what Mary Catherine Bateson, the academic, called a midlife atrium, some time and space to reimagine and repurpose and to be more conscious about how I wanted to curate the second half of my adult life.

0:10:40.7 Chip Conley: And that was amazing. We can go back to that, but I think everybody should have an atrium occasionally where they have some space and reflection to sort of rethink about what they wanna do with their life. 50 is not a bad age to do that at. At 52, I joined Airbnb in the early days of Airbnb as their modern elder, someone who's as curious as they are wise. And I was twice the age of the average person. I was 52, average age was 26. I was there to help support and mentor the founders, the three young founders. And that's how it all happened that like, oh, I'd started to notice I'm in midlife. I had had a really rough 45 to 50 in my early midlife. I was now having my 50s, which I loved. I was confused by the fact that I had had the worst of times and the best of times in midlife. And I was really curious why most companies and most people don't think about intergenerational collaboration where I was.

0:11:35.0 Chip Conley: I mean, I'm a boomer and I was surrounded by millennials. And it was all about, like, how do we create a great company, this Airbnb company? And ultimately, I spent seven and a half years there taking the company up to its IPO and helping support the founders. And I loved it. I worked on a book called Wisdom at Work, the Making of a Modern Elder about my Airbnb experience. And while I was writing that book and really doing research on midlife, I one day was running on the beach in Baja while I was writing the book. And I had a Baja aha, Paul. I had an epiphany, which was why are there no midlife wisdom schools? Why is it that we have no schools or tools or rites of passage or rituals for people in their 40s, 50s, and 60s in particular? And that's how MEA, the Modern Elder Academy, came about six years ago. We've had 5,000, almost 5,000 people from 48 countries come to MEA.

0:12:36.2 Paul F. Austin: Wow.

0:12:36.9 Chip Conley: And it's been really quite an experience to have that big of a global movement attached to what is the world's worst life stage in terms of its brand, midlife, which is known as a crisis, but I think of it as a chrysalis instead of a crisis.

0:12:55.4 Paul F. Austin: And I love these metaphors, the midlife atrium, the chrysalis instead of a crisis. One book that I read about a year ago or so was a book called Come of Age, the Case for Elderhood in a Time of Trouble. It's by a guy named Stephen Jenkinson, who's this Canadian writer...

0:13:16.2 Chip Conley: Yep. I know it.

0:13:16.4 Paul F. Austin: And fantastic, fantastic book. And it really brought me, and it's heavy, it's like, there's depth to it. There's like a certain level of weightedness to it. And a lot of what, even in the psychedelic world that I've reflected on is what's the role of rites of passage? How can psychedelics, plant medicine, transformational festivals even help to facilitate that rites of passage? And usually, I think about that in the context of a boy to a man, a 14, 15, 16, 18, 19-year-old. But I think there's also something to be said for this sort of second phase, which is how do we go into age with grace? And it's something that we, from a Western culture perspective, we don't do well for many, many reasons, which has a number of unfortunate consequences when we can't age gracefully. And part of that is seen in sort of this movement towards long...

0:14:19.4 Chip Conley: I would change your language to age gratefully, not gracefully. And I say that only because when we hear people talking about graceful, it's like a swan. You're supposed to somehow be poised. And the people I really appreciate are not the swans as they get older. It's the agitators. It's the ones who realize they wanna make a difference in the world. It's the ones who actually feel grateful about every single day. So it's just, I'm sorry to just give you my...

0:14:50.3 Paul F. Austin: No I love that.

0:14:51.4 Chip Conley: Subjective perspective.

0:14:51.6 Paul F. Austin: Thank you for the term.

0:14:53.3 Chip Conley: Yeah.

0:14:54.6 Paul F. Austin: Yeah. And so to sort of build on that, with your time at Airbnb in particular, what were some of the things that you were most grateful for in having that opportunity to help shape and guide such a influential platform in today's day and age?

0:15:15.2 Chip Conley: First of all, I think one of the things that, as you can tell, I like language. And I think one of the things that we have as a culture is this sense of we venerate youth. And, this is particularly true in the United States. But, as we get older, it's not about being youthful. It's about being useful. And when I was at Airbnb, I was definitely not youthful. I was used to being youthful because I started a boutique hotel company at age 26. Like, I was youthful. I was the young CEO. That's how the media portrayed me. But by the time I was 52 and twice the age of the average person in the company, I was not youthful. So what I really needed to do, and what I was grateful for, was to feel useful. And the modern elder is not about reverence, it's about relevance. So what I had to do is I had to look at what had I learned along the way that might be useful.

0:16:08.7 Chip Conley: But instead of having the okay boomer reaction by saying, like, hey, guys, sit around my feet and let me tell you how the world works, which is how sometimes boomers sort of react or respond to younger people as if we're supposed to be venerated, and you're just supposed to hang on my every word. Instead, I showed up with a curiosity and a desire to learn. Because at 52, I was joining a tech company for the first time. So I was a mentern, I was a mentor and an intern at the same time. I was mentoring around emotional intelligence and leadership. I was interning around digital intelligence. So EQ, I was providing EQ, and I was learning DQ, digital intelligence. And I was so, so amazed by the mutual mentorship I was having with people who were 20 and 25 years younger than me. So I felt grateful because I felt useful.

0:17:04.1 Chip Conley: I felt grateful because I saw the intergenerational collaboration and what that can offer in the world, not just in the workplace. I felt grateful because I could see the impact on Brian Chesky. So Brian Chesky is the co-founder and CEO of Airbnb. He's the one who came to me and said, we really want you to join us. And this was at a time when nobody had heard of Airbnb, and they were growing fast, but the hotel industry didn't even know it existed. And so here I am a hotelier in my whole life, and I'm gonna be becoming Darth Vader, gonna the dark side and helping what ultimately became the disruptors of the hotel industry. But when I joined, it was not a disruptor. It was not perceived as a disruptor. But to join and to be 21 years older than Brian, who I was mentoring, but also to be reporting to Brian because my role was the head of global hospitality and strategy, meant that I needed to have the stature of having something to help teach Brian, but also the sense of humility to be able to report to someone 21 years younger than me, who is my mentee. It was fascinating. And it worked really well. 7 1/2 years of time, I did that.

0:18:19.6 Chip Conley: And yeah, I think I'm really grateful for the fact that 3 1/2 years after their IPO, Brian is still the CEO as someone who's totally not trained in business. He went to the Rhode Island School of Design. He's a designer. He's the only in the Fortune 500. He is the only Fortune 500 CEO who has a creative background, who doesn't have any business background. So...

0:18:43.2 Paul F. Austin: Wow.

0:18:44.2 Chip Conley: Yeah, I feel a deep sense of I am what survives me. That's Erik Erikson, the developmental psychologist, came up with that statement long ago. And so over time, you really look at what impact you've had, the Ripples of Impact. That's the ROI that I focus on today, not the return on investment, but the Ripples of Impact.

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0:21:10.9 Paul F. Austin: I love that. I love that. So let's go a little bit deeper into to Modern Elder Academy. Let's say a lot of our listeners are in their 40s,50, 60s, who are tuning into the podcast. Many of them may be navigating this midlife chrysalis. Tell us just a little bit about what is, what is the path when someone is potentially interested in coming to the Modern Elder Academy and in sitting with you and in navigating workshops, what's the path of transformation that you're bringing them through? What are some of those core principles that you want to sort of impart into them as part of this academy?

0:21:44.7 Chip Conley: One of the key things for people to know is that we use rites of passage and rituals to help people often in a social context, to go through some kind of transition in their life. And when it comes to adolescents, man, do we have all kinds of social infrastructure to support it? Although, let's be clear that today adolescents are really challenged, but we have a lot of social infrastructure to support it. There's a word called middlescence that most of us have never heard of. Adolescence is in your teen years, middlescence is in your midlife years, and it's when you're going through hormonal, emotional, physical, and identity transitions. Similar to what you did in adolescence, but you're doing it on the other side. And you start puberty and then you have menopause. And it is like those are the bookends of your ability as a woman to be able to potentially have children.

0:22:33.0 Chip Conley: And so long story short is we do not have rites of passage or rituals or schools or tools for people in midlife. And we're going through all kinds of transitions. So there are really four key things to know about the MEA program. Number one is, we help people reframe their relationship with aging, because when Becca Levy at Yale has shown, when you shift your mindset on aging from a negative to a positive, you gain seven and a half years of additional life, based upon all kinds of social science research. So this is a bigger impact in terms of an intervention, helping add longevity, than if you stop smoking at 50 or you start exercising at 50. So helping people to see what gets better with age. And that's why my new book called Learning to Love Midlife: 12 Reasons Why Life Gets Better With Age, is the subtitle really tells you the story of the book.

0:23:21.5 Chip Conley: It's, we are very clear as a society, what gets worse with age. And that's why we have an anti-aging industrial complex, which is generally an anti-women complex. It's meant to make people feel badly about their natural process of aging. And so I really wanted to have a pro aging message with the book and with MEA. So the umbrella for the whole program is how do we help people feel better about getting older? The three key pillars in the program are how do we help people navigate transitions? And whether that's parents passing away, empty nest, divorce, menopause, changing careers, changing where you live, having some kind of new spiritual awakening. Richard Rohr, the famous Christian mystic who's on our faculty for MEA and an MEA alum says that the primary operating system for the first half of your life is your ego, and for the second half, it's your soul. But nobody told you in midlife there's an operating system change or gave you operating instructions. And so people are going through all kinds of transitions, but they don't really have words or roadmaps to understand it. So that's the first pillar.

0:24:27.5 Chip Conley: The second pillar of our program, and why people come is to cultivate purpose. So cultivating purpose helps people to say like, okay, I'm 50 years old now. Or I'm 45... One sixth of the people who come to MEA are millennials. So we've had people as young as 25 and as old as 88. Average age is 54. So it's not elderly, it's... You can be an elder as I was at 52 at Airbnb. What's his name? Tom Brady was a modern elder in the NFL as a quarterback in his early 40s. So cultivating purpose is a really important piece, because it is one of the ingredients for living a longer, healthier, happier life. But for a lot of people around midlife, they start to get bored, and they start to realize what's really problematic for them is that they have been doing the same thing over and over again. And they've actually been pursuing successism, which is like consumerism. Consumerism is trying to keep up with the Joneses in terms of your stuff. Successism is keeping up with the Joneses in terms of your LinkedIn profile. And you sometimes realize around midlife like, shit, I'm doing this for the sake of my parents, or for the sake of like, what other people think of me. This is not what I wanna do. So we have a lot of people who fit that profile too.

0:25:43.6 Chip Conley: And then the third is the most abstract of our three pillars, and it's called Owning Wisdom. And we live in a very knowledge-based culture. It's all about accumulating knowledge. So the first half of our life, we accumulate, the second half of our life, we edit, and it's our discernment and wisdom that helps us to edit. We do something, a ritual at MEA called the Great Midlife Edit at a fire. And it's really quite a beautiful experience, a collective ritual that helps people to let go of what's no longer serving them, whether it's a mindset or an identity, an obligation or just a something quite functional in their life that's become dysfunctional. So owning wisdom is important, because I actually think we're moving into an era of new wisdom traditions, and we live in a knowledge based culture, but it's all commoditized with AI and Google. And so what was really scarce is how do we metabolize our experience to create wisdom? And I think wisdom is metabolized experience, which leads, which you share, 'cause it's a social good. So I could go on and on and on, but that's a basic quick recap of what me is about.

0:26:53.5 Paul F. Austin: And one thing I wrote down here is you mentioned we're coming into these new wisdom traditions, and this is something I've talked about on the podcast pretty extensively and even what Third Wave represents. It's what's the middle wave between, let's say, the first wave of psychedelics, the indigenous use of these plant medicines for thousands of years, and the second wave of psychedelics, which brought science, precision medicine, sort of an objective nature to understanding the qualities of these mystical experiences. And you mentioned Santa Fe, I asked you when we started, why'd you move to Santa Fe? And you mentioned you had an uncle who worked with the Navajo Nation. And so I'm just curious to hear you flesh out a little bit more about what does indigenous wisdom mean to you? How has it influenced your perspective? How has it influenced the the Modern Elder Academy?

0:27:44.0 Chip Conley: What a great question. Thank you. And we have a shaman at our Baja campus, who has really helped me to see this. He's a good Mexican Jewish shaman. And so he's wonderful. His name is Saul. So the indigenous traditions, whether they're in Mexico or in New Mexico or anywhere in the world, there are a few key things to know. Number one is there's generational wisdom, and so there's even a brand in the United States, seventh generations or seventh generation premised on indigenous wisdom, which is you wanna make decisions that are gonna last seven generations. You're not thinking short term, you're thinking long term. So indigenous wisdom is often land wisdom. It's understanding how do we listen to the land? How do we have a regenerative spirit around the land? How do we move from what we're in right now, a very extraction perspective on the land and each other to one that is regenerative?

0:28:52.1 Chip Conley: And Paul Hawkin, who has written the book Regeneration and is on our faculty and lives within walking distance of our Baja campus. Really has amplified this quite a bit. So indigenous, so to me, something that's indigenous means that it's multi-generational, it's generation... It's multi-generational in terms of people having instead of age apartheid like we have in the US, where you have the young people over there and you have the old people in the retirement communities and they don't ever see each other. It's all very multi-generational, and it has ancestral thinking that you're thinking about how can you be a good ancestor. I'd say that's one, probably the most important piece of indigenous elderhood is. And a belief in a respect for nature as your friend, you don't extract from a friend, you build up a friend. So that's a big piece of it.

0:29:48.4 Chip Conley: I think the idea of there being mystical, almost impossible to describe ethereal epiphanies that can come into your life if you create the space, the sacred space for them to come through you is very indigenous. And that's again, not about accumulating knowledge, it's about learning how to channel wisdom. And so I would say a indigenous point of view would be one that says if I create the conditions for wisdom to come through me, the chances are that will happen, but not necessarily on my time, on someone else's time. And so there's an element of the indigenous culture that believes in wisdom, believes in epiphanies, believes in creating the sacred space for spirit to come through you.

0:30:43.5 Chip Conley: I think beyond that, those two are pretty meaty subjects right there. I think maybe I would just say beyond that, don't judge something by what's on the surface and I think that that's what I've seen. And again, that relates a little bit to number one and two, but I think there's a relevance there too. And this is why I think about our shaman Saul, and I think about our poet cowboy who's a bit of a shaman here in Santa Fe, Lee. There's an intuition that they're tapping into that. Again as I said in the second thing, the idea of wisdom comes through you, but it's being able to see someone and being a first class noticer. So it's not about just something coming through you, which could happen to anybody if you just create the right conditions, but it's your skill at being able to be a first class noticer and that's I think something that you get better at as you get older. Actually, I think children, babies are actually quite good at it. I think it's frankly, when we go into our knowledge era, between age maybe six and age 46 or 56, where we lose it, because we get so distracted by being on the treadmill, being full of knowledge, et cetera.

0:32:08.9 Paul F. Austin: Yeah. There's a phenomenal book I read about a year or two ago called Spell of the Sensuous by David Abram. And in that book, David, it's fantastic. Yeah.

0:32:20.2 Chip Conley: I love the book.

0:32:21.5 Paul F. Austin: And he talks about how we've... Especially in the last 300, 400 years, because of this industrial sort of uplifting of the world and society, we've become over-indexed on linear, on writing, on knowing. And in that we've lost touch with this deeper sort of not only oral traditions, but this animist way of sensing and breathing and living with nature, right? And it almost feels as if animism which I've noticed with psychedelics. When people work with ayahuasca, when they take mushrooms, it's opening up this awareness of a worldview or a perspective that we've been sort of cut off from for a long, long time, right? And so that sense of intuition is important, and where I'm going with that is, I'm so glad you mentioned this multi-generational wisdom, because one, one sort of polarity I love to set up is the typical VC hockey stick for exiting a company is seven years. And multi-generational wisdom is seven generations. And so I'm curious to hear some of your reflections on, especially as we're stepping into this sort of sense of becoming elders. From a business perspective, from a leadership perspective, what can we learn or how can we shift that lens from seven years to seven generations?

0:34:04.0 Chip Conley: Oh, there's so many initiatives out there, including the long-term stock market, but so few of them actually get off the ground in the mainstream kind of way. I can only speak for it on a personal level. I think how do we help train people to become modern elders? And to become a modern elder is just someone who's as curious as they're wise, and they have a spirit of generativity. So generativity is a word that Erik Erikson, the developmental psychologist claimed 70 years ago. And the premise behind generativity is, it was the seventh of eight life stages, really midlife. And generativity is when you start to realize that you have a challenge at this stage, it's either generativity or stagnation. Generativity as a word basically means you are here to generate things that actually support future generations.

0:34:57.2 Chip Conley: And so it really speaks to the idea of mentorship, et cetera, and historically it's been very top down, to be honest with you. And today, I think it's much more symbiotic. The physics of the waterfall is moving up from young to old also, because I learned as much from the young people at Airbnb as they learned from me. So long story short is, the idea that we can be generative, and have that kind of relationship with each other where it's like in an intergenerational potluck, and everybody brings to the table that which they know best. And that's really I think what's been at the heart of my work. And I think helping people to see that and then on a personal level that you have that capacity. And then at the corporate level, you don't only go out. I go out and give a ton of speeches to HR departments and CEOs to help them to see the value of age diversity. And that goes on both sides. Age diversity, ageism can happen toward older people, and that's where I tend to focus. But it happens to young people too, where you're in your old school traditional firm, and if you're in your 20s, you don't have any voice.

0:36:10.9 Chip Conley: Now of course at Airbnb it was quite the opposite, but it was, the reality is that we need to see that we have so much to learn from each other. And unfortunately, only 8% of Fortune 1000 companies use age as a metric to look at their DEI function. So they look at race and ethnicity, sexual orientation and gender, but they do not look at age. And yet, age diverse teams have been proven over and over again to be even more effective than just about any other kind of diversity, partly because a young brain and an old brain, older brain operate differently. The young brain is fast and focused, the older brain is more synthetic and holistic. It's the difference between fluid intelligence and crystallized intelligence. So, long story short is, I am just an activist for this message.

0:37:00.5 Paul F. Austin: And almost what I'm hearing in that, that response chip is maybe a way that we can help businesses to have that broader context of generativity and multi generational lens is age diversity. It's how are we bringing, like even Airbnb did with bringing you in as a sort of in-house elder to help mentor and guide them. How can we, even in these younger companies that maybe have great ambitions, still ensure that there are elders in the room that can help people to navigate and guide decisions? 'Cause there's a lot of... Especially, and I say this being I'm 33. In my 20s, I'm really only thinking three years ahead, five years ahead at the very most, I'm not thinking necessarily 20 or 30 years ahead. And having that broader lens can often be very, very useful to ask these deeper questions, especially about purpose and mission. If business is less and less about simply scaling as big as we can, and more about serving the souls of people who are engaging with us, our customers, if you will, then I think there's a really beautiful way that businesses align with these regenerative communities and sort of what's coming out of that ethos.

0:38:23.0 Chip Conley: Totally agree. I mean, it's... And let's... Here's an interesting stat, Paul. The US Department of Labor says that in 2025, the majority of Americans will have a younger boss. Now, we've never seen this before. We've never seen a workplace in which older people are reporting on average to younger people. Now, in many cases, it may just be like, oh, my boss is two years younger. But in my case, I was... My boss is 21 years younger. And my situation was not... Is not unusual. And it's because... And as people stay in the workplace longer by choice or necessity, which is actually happening and as we become more digitally focused as a culture, we're gonna see this. We're gonna see 65 year olds reporting to 35 year olds. And they both have something to learn from each other. But this is a new phenomenon. And yeah, so I think we gotta get good at this.

0:39:23.2 Paul F. Austin: And it almost speaks to the importance of, regardless, as you mentioned, of age difference and regardless of job title, there's something that's very, I think, important about seeing eye to eye. In other words, the less hierarchy there is and the more there's a recognition of you have a gift to give and you have a gift to give and we're here to give our gifts. And how do we create coherence for those gifts to serve the people that we most want to serve? I think that lens can often help. And that way I experienced this. I'm a CEO of a small company. We have about 12 employees, but almost everyone is older than I am and has been. And so I've had to learn, how do I navigate that?

0:40:09.7 Chip Conley: Wait, did you say that they're all has-beens? Everybody who has been older, you said, and I said, like, are they all has-beens?

0:40:21.9 Paul F. Austin: No, no, no, no. Most, most, most, some, some were younger, but I've even reflected on that. Like, why is that? And I think where I've been very fortunate is through Third Wave, I've just developed a mission that really speaks to people. It's the cultural acceptance of psychedelics. People have these really meaningful experiences and they go, I want to get behind this. And so even from a leadership perspective, I've always looked at what, how do we shift more into stewarding, right? Stewarding wisdom and intelligence and coherence rather than thinking of it more from a leader perspective that I have to lead from the front and I have to push everything forward, right? There's a sense of really, yeah, listening and welcoming in and drawing out the intelligence and wisdom of sort of a diverse cast of characters, if you will.

0:41:08.8 Chip Conley: Yeah. For me, on a personal level, it's been moving from the hero, moving from being the hero, the can-do-it hero. I can do it. I can do it. We can do it. Moving from can-do-it hero to the conduit and the conduit, what can come through me and how could I be the conduit coach, such that my role is not to be the can-do-it hero, but it's to be the conduit coach, have something come through me. As I said earlier, when you create the conditions for wisdom to come through you, but to have it come through you, not to stroke your ego because you're the hero solving the problem, but because you're the one who's actually supporting, you're the confidant, you're the one who gives people confidence. That is one of my definitions of mentor, is it's not just someone who has all the answers. That's a librarian. A librarian has all the answers.

0:42:00.4 Chip Conley: A confidant is the one who gives you confidence. And a librarian is a perfectly fine form of mentor, too. That's where a mentee asks someone a lot of questions who's older, and you learn from that. But the more powerful relationship is a confidant relationship, where it's the mentor, the confidant, asking the mentee questions and helping to guide them on a roadmap like a permissionary. You're in the business of giving people permission to go for it, but you're also giving them the roadmap that will enhance their likelihood of success, and more importantly, enhance their ability to get to know themselves. Because a great confidant and mentor is less interested in what they get out of it and more interested in supporting that mentee to become the best that they can be. And that was my relationship with Brian Chesky at Airbnb and why I do feel this wonderful sense of, I don't know, it's not pride, it's not the right word. It's a wonderful sense of being useful, but because he's still the CEO of that company.

0:43:06.2 Paul F. Austin: And you're also doing that now through the Modern Elder Academy, where for all the reasons that you mentioned, a lot of people as they hit this midlife chrysalis, they enter this liminal space. And you mentioned Richard Rohr before. Richard Rohr has a phenomenal essay about liminality. And sometimes we have to forget and lose track and not know and not understand to really chart and navigate that liminal path. And so how do we give confidence as confidants to people as they navigate that liminal space, which is so often terrifying, but also necessary to navigate?

0:43:46.0 Chip Conley: Yeah, exactly. And Richard is a real supporter of thinking around psychedelics and thinking around just how we as a society can look at alternative ways of connecting with spirit. For those who don't know Richard, Richard is a well-read and really prolific Catholic priest who became a real Christian mystic and has helped people to see that there are many different paths to the divine. And so I really appreciate him for that.

0:44:24.9 Paul F. Austin: So I think you mentioned you're on the founding board of Burning Man, or you're still on the board of Burning Man, is that... That's correct?

0:44:35.2 Chip Conley: Yeah. Founding board member of the Burning Man non-profit. So about 15 years ago, the six founders of Burning Man decided that they wanted to take a for-profit, which was actually what Burning Man was, and gift it to a non-profit. And so I was lucky enough to be the first person they asked to say Chip, we want you to sort of help lead the effort of moving this for-profit to a non-profit and then growing it and having it become something bigger than it has been. And so yeah, so I have a long history there. I helped to buy Fly Ranch, which is the 3500 acres near the Black Rock City in Nevada, which is meant to have long-term seventh generation thinking about how Burning Man can have a future that's way beyond what the Bureau of Land Management will allow, which is where Burning Man, the event happened. So yes, and therefore I have way before Burning Man, I have dabbled in and experienced psychedelics since I was in college and have seen the remarkable value, both in college, but all the way since then. Although there was a 15-year period where I just was sober, alcohol, and any kinds of intoxicating substances.

0:46:06.2 Chip Conley: But I actually do think that in midlife, psychedelics can be very helpful because one of the challenges with midlife is that people need to break out of their habit, their habits, and have a new habitat. And when we think of a new habitat, you often think of a new place that you are. But I want to think, I want everybody here to think about, it's not just the place physically, it is the place psychologically, emotionally, spiritually. And the beauty of psychedelics is it helps break you out of the box that you're in and helps you see things, both externally and internally, that you wouldn't have seen otherwise. So I will say that I properly administered and properly making sure that people don't get addicted to whatever it is, what a beautiful tool it can be toward someone feeling the transcendence that I think really is ideally what we all aspire to.

0:47:11.0 Paul F. Austin: Right, that state of being. And then, of course, the question which you started to open up is, what's the habitat that we inhabit that can turn that sort of somewhat fleeting state into more of a trait, a way of being, the way we choose to navigate reality? And I think that's something, as I was doing a little bit of digging and research and talking with a few friends my sense is you have Modern Elder Academy, yes, but there's a larger vision and picture here around regenerative communities. And we've already talked about generativity, we've already talked about sort of the nature of regenerative. So I'd be curious just to start there Chip Conley vision when it comes to this overlap of Modern Elder Academy and regenerative communities, what are you building? What are you sort of stewarding in the world at that intersection?

0:48:03.4 Chip Conley: Well, I want to give proper credit to my two co-founders, Jeff Hamoui and Christine Sperber, who have really opened my eyes to the value of regeneration when it comes to the land. Of course, Paul Hawken has done that as well. And so in Baja, what we heard from our alumni was like, gosh, I love coming for a workshop for a week, but I'd love to live like this in this regenerative spirit year round. And so we created a regenerative community, 26 homes around a regenerative farm a walk from our campus. And the whole premise is that instead of retirement communities, what if we had regenerative communities? Because retirement is about learning how to frankly, I think with the word retirement, or retire means to withdraw into seclusion, which is sort of what retirement communities are. They're like age apartheid.

0:48:58.5 Chip Conley: And instead, regeneration is about giving life to something, providing vitality. And you can think of that selfishly, but actually what we think about is like, how are we giving regeneration to the community and to the soil and to the community, the locale, the broader community, and then also the community of people living together? Wouldn't it be interesting to live in a community in which there's a potluck every Saturday night for everybody who lives in the community? Anybody who wants to come. And you go out and harvest some vegetables that afternoon in the farm to do it. So it's like, there's a lot to it. And we're going to be doing the same here in Santa Fe, New Mexico. So the broader vision is, how do we create regeneration globally by creating a role model for it? And how do we create a proof of concept? And that's part of the reason we wanted to move from just, we not move, but go from what we've done in Baja with a campus on the beach and a regenerative community called Baja Sage, to doing a proof of concept in Santa Fe with a 2,600 acre regenerative horse ranch, outside of town, a campus in town that'll open in two or three years, a former Catholic retreat center and seminary. And then thirdly, a large plot of land, 330 acres, that will be a regenerative community.

0:50:18.1 Chip Conley: So long story short is it's a big vision. And there are moments when it's hard for me because I just feel like, wow. But the beautiful thing about it is I just got an email yesterday from someone who was in a workshop with me two weeks ago. And I teach a lot of the workshops, but definitely not all of them. The majority are not top, I mean. But it was somebody who was in the workshop and he was an NBA, I won't say this name, but he was an NBA president and general manager of a franchise. And he lost his job. He lost his job. And he'd been in the NBA for 29 years. And he lost his identity because so often, especially for men in our culture, their business card is their identity. And he was really lost, but really curious also. And so yes, there's a big vision for what we're doing. But when I got this email from him yesterday and his level of inspiration from the experience of being a week in Baja with us was such that it was palpable and I could see how it was going to make an enormous difference in his life. That's the thing that's the ripple of impact I'm more focused on. Yes, the role model, the inspiration, the global movement, all that's great. But it starts with one by one, how are you having an influence on individuals? And that's really what keeps me going.

0:51:48.5 Paul F. Austin: And so I want to bring this full circle now and even talk about something we haven't yet really gone into, which is you founded the second largest Boutique Hotel Chain in the United States. And I'm curious, what lessons from those years are you now looking to apply to this new project around regenerative communities? What do you think was very valuable about those years? And maybe also, how is this different than that initial initiative of building out what you built?

0:52:23.5 Chip Conley: Yeah, well, I think a lot of my ego was attached to being that CEO. So that the guy I was just talking about, the NBA executives like, hey, that was me too. And while I didn't get to the point where I got fired because I was the CEO of my company, I did get to the point where I had to sell it at the bottom of the great recession for a lot less money than I could have made, but I didn't want to do it anymore. I had had an NDE, I had died and gone to the other side nine times in 90 minutes due to an allergic reaction to an antibiotic. And it was like, whoa. So the way I'm trying to operate now is coming from that place of no longer being the hero, no longer having my whole identity attached to my job title, and instead really see that my job is to help others and to be in service and to more than anything, to be in a place where the mission's going to outlive me and I am what survives me.

0:53:26.4 Chip Conley: And that really defines how I'm looking at it now. Whereas with the Boutique Hotel Company, I got my name on the cover of magazines a lot. And I loved the fact that people really liked staying in our hotels and eating at our restaurants, going to our spas. But it was very much of an ego-fed proposition. And I can't say that I don't have an ego anymore, I do. But I've learned to let my soul lead the dance. When I was in sixth grade, I went to ballroom dancing school. And I learned as a boy how to lead the girl into dance. And for the first half of our life, for many people, the ego is leading the soul in the dance. And the soul is having to learn how to be in heels going backwards. And as you get older, you realize, my God, it's changed. The soul is now leading the dance. And the ego has to learn how to be in heels going backwards. And therefore, the ego better have a sense of humor because it's not very used to that. And that's, I think, one of the things that's been a beautiful thing in my life today. And Richard Rohr has been very helpful for me on this, is to see how much I can laugh at myself. What Richard says is, we all need a humiliation today, hopefully nothing too big. And what he means by that is, our humor and our humility and our humanness are all together. But a little humiliation today reminds you to have a sense of humor.

0:54:54.3 Paul F. Austin: A good friend of mine, we were talking about, I think, Elon Musk at some point. And one reflection that we had was, he does a phenomenal job of balancing levity with gravity. That it helps to have depth. It helps to have...

0:55:09.9 Chip Conley: Gravitas and levity. This is what I say...

0:55:13.8 Paul F. Austin: Exactly.

0:55:15.4 Chip Conley: As we get older, we are alchemists, extrovert, introvert, curiosity, wisdom, gravitas, levity, yin yang, masculine, feminine. There you go, my friend. Totally agree.

0:55:28.1 Paul F. Austin: I love it. I love it. I love it. Well, Chip, so just so listeners know, you have a book that was recently published, Learning to Love Midlife. We mentioned it a little bit, 12 Reasons Why Life Gets Better with Age. I would encourage everyone to check that out. It's available now. Modern Elder Academy. Is that if folks want to learn more about?

0:55:50.8 Chip Conley: The easier way is, And I have a daily blog there called Wisdom World. So if any of this was interesting to you, it's a free blog, free subscription. You get an email to me for a little microdose of wisdom every morning.

0:56:10.1 Paul F. Austin: Nice. I love it. Well, Chip, thank you for everything that you've created, the way in which you mentored and helped support Airbnb to navigate an incredibly explosive and pioneering space. And for what you're now doing through the Modern Elder Academy, I think it's so necessary and important. And I'm just really grateful that we had a chance to drop in for a little bit on the podcast today. So thank you.

0:56:38.1 Chip Conley: Paul, thank you.

0:56:42.9 Paul F. Austin: Hey, listeners, Paul here. I hope you enjoyed our episode today with Chip Conley. We'd love to know what you thought of the conversation. And you can let us know in Third Wave's community, our free platform where you'll find support, discussions, as well as education resources and providers across our global ecosystem. Sign up for free at Thanks for tuning in and we'll see you next week.

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