Embracing Midlife: Wisdom, Growth, and Reinvention With Chip Conley

Embracing Midlife: Wisdom, Growth, and Reinvention With Chip Conley

by | Podcast

Chip Conley is the Founder and Executive Chairman of Modern Elder Academy (MEA), the world’s first “midlife wisdom school” dedicated to career and life transitions. At 26, he founded Joie de Vivre Hospitality, transforming it into the second-largest boutique hotel brand in the US. In 2013, Chip joined Airbnb as Head of Global Hospitality and Strategy, mentoring its founders and shaping its culture. He is also a sought-after keynote speaker and prolific author, with several influential books to his name, including Wisdom@Work: The Making of a Modern Elder and his latest bestseller, Learning to Love Midlife: 12 Reasons Why Life Gets Better with Age.

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Here’s a Glimpse of What You’ll Hear:

  • [2:32] Chip Conley’s unexpected journey from hotelier to Airbnb’s modern elder
  • [4:36] Challenges of shifting from CEO to mentoring a younger leader
  • [8:49] The tension between technology and hospitality in Airbnb’s growth
  • [11:36] Why Chip faced criticism from the hospitality industry after joining Airbnb
  • [15:38] The inspiration behind founding the Modern Elder Academy (MEA)
  • [19:52] The impact of shifting from a fixed mindset to a growth mindset in midlife
  • [22:09] Chip’s battle with cancer while launching a book and expanding MEA
  • [25:41] Why midlife can be the most fulfilling stage of life
  • [27:14] How the MEA curriculum helps individuals navigate career and life shifts
  • [32:47] Why a midlife sabbatical should be a standard part of every career

In this episode…

Many people approaching midlife struggle with uncertainty, questioning their purpose, relevance, and ability to adapt to change. Society often reinforces the idea that aging means decline, leaving individuals feeling stuck in careers or personal lives that no longer fulfill them. So, how can individuals in their middle years shift from feeling irrelevant to flourishing?

Chip Conley, a veteran hospitality entrepreneur, author, and speaker, challenges these outdated notions by reframing midlife as a period of reinvention and renewal. Drawing from his journey — from building a boutique hotel empire to mentoring young tech leaders at Airbnb — Chip emphasizes the power of curiosity, adaptability, and lifelong learning. He shares practical strategies, including shifting from a fixed to a growth mindset, embracing intergenerational collaboration, and taking intentional sabbaticals to reset and gain clarity on life’s next chapter.

Tune in to this episode of the Smart Business Revolution Podcast as John Corcoran interviews Chip Conley, Founder and Executive Chairman at Modern Elder Academy, about harnessing the potential of middle life. They discuss how Chip navigated his transition from hotelier to tech mentor, the challenges of leading while learning, and the impact of longevity on career planning. He also shares the philosophy behind MEA’s curriculum and the importance of a midlife sabbatical.

Resources mentioned in this episode:

Special Mention(s)

Related episode(s)

Quotable Moments:

  • “A modern elder is someone who’s as curious as they are wise.”
  • “Our best years may be ahead of us.”
  • “Death is a very, you know, exquisite organizing principle for how you live your life.”
  • “Midlife is a chrysalis, that transformational life stage between the caterpillar and the butterfly.”
  • “A cultural shift such that at age 50, we all take a minimum of a three-month sabbatical.”

Action Steps:

  1. Reframe midlife as an opportunity: Shift your perspective from seeing midlife as a crisis to viewing it as a time for reinvention and growth.
  2. Balance wisdom with curiosity: Approach new challenges with experience and a willingness to learn, ensuring continuous personal and professional development.
  3. Take intentional sabbaticals: Periodically step away from routine responsibilities to gain clarity, reset priorities, and explore new directions in life and career.
  4. Embrace intergenerational learning: Seek relationships with people of different ages to exchange knowledge, gain fresh perspectives, and foster mutual growth.
  5. Design your next chapter with purpose: Identify what excites and fulfills you, then take strategic steps toward building a meaningful and rewarding future.

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Episode Transcript

John Corcoran: 00:00

All right. Today we’re talking about a new topic: how to learn to love middle life. For those of you who are maybe in that phase of life or heading towards it or just beyond it, I think this will be a relevant topic for you. My guest today is Chip Conley. I’ll tell you more about him in a second, so stay tuned.

Intro: 00:20

Welcome to the Smart Business Revolution Podcast, where we feature top entrepreneurs, business leaders, and thought leaders and ask them how they built key relationships to get where they are today. Now let’s get started with the show.

John Corcoran: 00:36

Hi. Welcome everyone. John Corcoran here I am, the host of this show. You know, each week I get to talk to interesting CEOs, founders and entrepreneurs from all kinds of different companies. We’ve had Netflix, Grubhub, Redfin, Gusto, Kinkos, YPO, EO, Activision Blizzard, lots of great episodes.

Go check out the archives. And we’ve had lots of different speakers and authors on different topics. Today’s topic is a really interesting one and not one that you see covered very often. So my guest here today, first of all, before I get to him, I have to thank Tony Lillios, who’s a past guest on my podcast. He’s a personal professional coach.

Check out his website at lillios. Great guy. He told a great story about his life journey. But he introduced me to today’s guest , Chip Conley. And you’ve probably seen him interviewed before.

He’s the Co-founder and Executive Chairman of MEA Modern Elder Academy. He previously founded Joie de Vivre Hospitality. We’ve got a bunch of those in my area. I’m here in the San Francisco Bay area, so I’m very familiar with it. But it became the second largest boutique hotel brand in the US.

And then in 2013, he became the head of global hospitality and strategy at Airbnb, where he mentored the founders and helped shape the company’s culture during a period of rapid growth. And then that led to his interest in middle life, creating a midlife wisdom school. Sorry, I gotta get that right. Midlife Wisdom School, has campuses, a couple of different campuses, Baja and Santa Fe. I believe it is.

And so we’re going to talk about that. But I wanted to start now. You’ve done interviews on all kinds of different topics, but I wanted to start with your experience at Airbnb because that’s what really inspired the current phase of what you’re focused on now. And you had an experience where you would start your hotel at a young age. You were pretty young.

And so you’re the young buck doing it for many years. And then you were brought into Airbnb when Airbnb was still a much smaller company to mentor the founders there. And then all of a sudden, someone refers to you as an elder. What did that feel like?

Chip Conley: 02:32

Yeah. So it’s great to be here. John, thank you for inviting me. And I started when I was 26 years old. So, to be a CEO of a boutique hotel company at that age was quite unusual.

And then growing it to 52 boutique hotels. You know, I was always perceived as way ahead of my age in terms of what I was doing. And then, you know, I sold the company and it’s a Hyatt brand now called JDV and had a couple of years off. At age 52, was asked by the founders of Airbnb 12 years ago to come in and help their little tech startup become a global hospitality brand. And within the first month, they started calling me their modern elder and I was like, well, what the hell is that?

You’re making fun of my age. And they said, well, you know, let’s recognize you’re 52 and the average age here is 26. So you are, relatively speaking, older than other people, and an elder is older than the people around them. But then they said the thing that really got me that I loved. They said, Chip, we think a modern elder is someone who’s as curious as they are wise.

They don’t have all the answers. Sometimes, they ask great questions. And you’re 52, and you’ve never been in a tech company before, so sometimes you’re learning something from us. But most of the time we’re learning something from you. And that was really that defined my seven and a half years at Airbnb, where we took this little tech startup and turned it into the most valuable hospitality company in the world.

And so, yeah, I didn’t mind the modern elder label once I understood their logic behind it, which was to say someone who is a modern elder is not about it’s not about just referring to them. It’s not about reverence. It’s more about relevance. And that combination of curiosity and wisdom.

John Corcoran: 04:29

Did it take a while for you to get your footing in Airbnb to figure out where you fit in, just floating around that scene?

Chip Conley: 04:36

You know, I think the hardest thing for me, John, was it was twofold. One was I was CEO for my own company for 24 years, and now I am the CEO whisper, whisper, whispering to Brian Chesky, the CEO who was 21 years younger than me. And I was reporting to him. So that was hard, you know, to go from CEO to all of a sudden whispering to the CEO, sometimes feeling like I knew a lot more than the CEO, but didn’t want to sort of pull rank. And, you know, based upon being the older one with more experience.

So I had to learn that. I also had to learn the tech business. You know, Airbnb was a tech company. It was full of techies, and I had no background in tech at all. So the combination of those two things required me to be open to learning.

And that was good, you know. But it did mean in the first couple of months, I had to get really comfortable that this was going to feel very transitional for me. This was not what I was used to. And I think that was helpful because quite frankly, by the time you’re 52, especially if you’ve been running a company for 24 years, been in the same industry for, you know, most of your career, you could be bored, you could be sort of like, you know, think you can’t learn anything new. And that’s, you know, unfortunately, that puts you into a death spiral in terms of losing curiosity, losing an interest in learning.

John Corcoran: 05:59

Yeah, there must have been moments while working at Airbnb, where everyone kind of turned to you or, you know, you had to kind of gauge. Should I offer an opinion here? Would I be undermining Brian if I offer this opinion now? Should I hold on to it? Tell him later. I mean that just navigating those dynamics can be quite complex.

Chip Conley: 06:21

Well, to actually be mentoring my boss, which was technically what was happening. Yeah, I was his mentor, but I was reporting to him. We had to deeply build a relationship that had a lot of trust in it. And so I had to be very careful about what I said, both in a meeting I learned to mentor privately and intern publicly, which means if I felt like Brian needed some And guidance about how he was leading or running a meeting or, you know, doing, thinking about something. I needed to do that one-on-one with him as opposed to in a group of people.

The good news is he was so wise at a young age, so open to learning. You know, this would not have worked without him being very motivated to learn and vice versa. Me too. But yeah, it was an unusual relationship in the sense that I was reporting to someone 21 years younger than me who had no business background. In fact, Brian is where.

John Corcoran: 07:26

Graphic designers, right? Yeah.

Chip Conley: 07:28

Brian went to the Rhode Island School of Design. He had no business background, no entrepreneurship background. And he has now for four years been a CEO of a public company, a Fortune 500 CEO, the only Fortune 500 CEO who has a designer or creative background. No one else amongst the Fortune 500 has a CEO. As a CEO has a background that is not being a lawyer, you know. You know, somebody who comes from a sort of classic business.

Yeah. And so Brian is a unique character in that. But he’s good, he has a good business mind. And so I felt like I was teaching him, and he was learning and had a big appetite.

John Corcoran: 08:11

And there must have been tensions. You know, I live here in the Bay Area in San Francisco. A lot of times it’s a product focus. Everyone focuses on improving the product. There must have been tensions between that and hospitality.

I just read the book Unreasonable Hospitality by Will Guidara. A great book and talked a lot about just, you know, in the hospitality world, just like doing everything you can to please the end consumer or customer. You know, but there must have been tensions at times where there were debates over, you know, how much effort and energy to put into improving the product versus the customer experience.

Chip Conley: 08:50

Yeah. You know, it was yeah. Ideally if you’re a tech company, you do not. You want to get everybody to your website and you don’t necessarily want to have, you know, human-to-human contact because that costs money, right? And we were doing all kinds of things in the, in, in real-life world where we were creating an Airbnb open, where we had 20,000 hosts from around the world, from 110 countries come to Los Angeles and Paris and in San Francisco for these events.

So we were really trying to be a hybrid, because what we knew is the soul of the company could not be conveyed purely based upon the website. At the same time, we were a tech company first and foremost, and so the product was really important. And, you know, I would say we’re one of the tensions in the early days. I deeply wanted to focus on quality, and there was a whole growth team within the company whose only responsibility was to.

[!no name provided!]: 09:55

Getting numbers right. The number of hosts we have.

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