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Brian Chesky's secret mentor who scaled Airbnb (after dying 9 times & building a hotel empire)

Brian Chesky's secret mentor who scaled Airbnb (after dying 9 times & building a hotel empire)

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Chip Conley is the founder of Joie de Vivre hotels, the second-largest boutique hotel brand in the world. At age 52, he joined Airbnb as Head of Global Hospitality and Strategy, reporting to CEO Brian Chesky, who was 21 years younger. He earned the title of Airbnb’s “Modern Elder” by guiding the young founders on leadership and culture while learning Silicon Valley’s tech mindset himself. Today, Chip leads the Modern Elder Academy, the world’s first midlife wisdom school, and is the author of best-selling books like Wisdom@Work and Peak. He champions the idea that age and experience are assets—and that midlife can be a launchpad for renewed purpose and impact. *In this conversation, we discuss:* 1. The reality of Brian Chesky in “founder mode”—the good, bad, and stressful 2. How Chip went from running 52 boutique hotels to becoming Airbnb’s in-house mentor in his 50s 3. The “mentor and intern” mindset: how to simultaneously teach others and stay curious like a beginner 4. Why AI might actually favor older workers (hint: human wisdom vs. artificial intelligence) 5. His framework for navigating midlife transitions and finding meaning after 40 6. Specific tactics for older professionals to thrive in tech companies 7. Surprising data that midlife is often the happiest time of life—and how to leverage your 40s, 50s, and beyond 8. Chip’s formula for managing anxiety and fear (and how to regain control when worry strikes) *Brought to you by:* Great Question—Empower everyone to run great research: https://www.greatquestion.com/lenny Vanta—Automate compliance. Simplify security: https://vanta.com/lenny Coda—The all-in-one collaborative workspace: https://coda.io/lenny *Transcript:* https://www.lennysnewsletter.com/p/chip-conley *My biggest takeaways (for paid newsletter subscribers):* https://www.lennysnewsletter.com/i/168435278/my-biggest-takeaways-from-this-conversation *Where to find Chip Conley:* • LinkedIn: https://www.linkedin.com/in/chipconleysf/ • Website: https://chipconley.com/ • Modern Elder Academy: https://www.meawisdom.com/ • Podcast: https://www.meawisdom.com/podcast/ *Where to find Lenny:* • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ *In this episode, we cover:* (00:00) Introduction to Chip Conley (04:30) Chip’s journey with Airbnb (11:44) Insights on working with Brian Chesky (18:27) Tactics to be effective when working with founders in founder mode (21:08) The value of intergenerational collaboration (27:03) Addressing ageism in tech (31:18) Advice for thriving as an older individual in tech (35:01) Advice for hiring managers (42:37) Chip’s early career and founding Joie de Vivre (44:12) A life-changing near-death experience (47:51) The importance of company culture (52:20) The Peak Model (57:09) The Modern Elder Academy (MEA) (01:00:30) The upside of aging (01:06:43) Who MEA is for (01:08:05) AI in daily life (01:10:20) Lightning round and final thoughts *Referenced:* • Brian Chesky on LinkedIn: https://www.linkedin.com/in/brianchesky/ • Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach • Natalie Tucci on LinkedIn: https://www.linkedin.com/in/natalietuccishoff/ • Laura Modi on LinkedIn: https://www.linkedin.com/in/laurahughes6/ • How to build a cult-like brand | Laura Modi (Bobbie): https://www.lennysnewsletter.com/p/from-growth-to-slowth-the-making • George Tenet: https://en.wikipedia.org/wiki/George_Tenet • Joie de Vivre Hospitality: https://www.hyatt.com/jdv-by-hyatt/en-US • Fest300: https://en.wikipedia.org/wiki/Fest300 • John Q. Smith on LinkedIn: https://www.linkedin.com/in/johnqsmith/ •Will A.I. Replace New Hires or Middle Managers?: https://www.nytimes.com/2025/07/07/business/ai-job-cuts.html • Burning Man: https://burningman.org/ • Sheryl Sandberg on LinkedIn: https://www.linkedin.com/in/sheryl-sandberg-5126652/ • Bill Graham: https://en.wikipedia.org/wiki/Bill_Graham_(promoter) • Maslow’s hierarchy: https://en.wikipedia.org/wiki/Maslow%27s_hierarchy_of_needs • Measuring what makes life worthwhile: https://www.ted.com/talks/chip_conley_measuring_what_makes_life_worthwhile • Jonathan Mildenhall on LinkedIn: https://www.linkedin.com/in/mildenhall/ • Becca Levy’s website: https://becca-levy.com/ • Kabuki Springs & Spa: https://kabukisprings.com/ • How positive age beliefs can support positive health outcomes with Becca Levy, PhD: https://www.ama-assn.org/delivering-care/population-care/how-positive-age-beliefs-can-support-positive-health-outcomes-becca • The U-shape of Happiness Across the Life Course: Expanding the Discussion: https://pmc.ncbi.nlm.nih.gov/articles/PMC7529452/ ...References continued at: https://www.lennysnewsletter.com/p/chip-conley _Production and marketing by https://penname.co/._ _For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com._ Lenny may be an investor in the companies discussed.

Segments Timeline

1
0:00 - 2:02
2:02 duration425 words

Joining Airbnb: A Midlife Journey

Chip Conley shares his experience of joining Airbnb at the age of 52, surrounded by a much younger team. He discusses the challenges of mentoring Brian Chesky while also being his subordinate, highlighting the need for humility and curiosity in a fast-paced tech environment.

"Let's paint a picture of just what it was like to join Airbnb in your 50s. I was mentoring Brian, but he was also my boss. I was 52. The average age was 26. I had to be both wise and curious and often..."

2
2:02 - 4:30
2:27 duration418 words

The Reality of Founder Mode

Conley reflects on the dynamics of working under Brian Chesky, emphasizing the intensity of founder mode. He describes how Chesky's expectations for work pace and commitment posed challenges, especially for someone with a diverse range of interests and experiences.

"conversation, we explore how to be successful in tech as you age. What he's learned working with and for Brian Chesy, including a lot of real talk, how to build a great culture at your company, his ne..."

3
4:30 - 6:00
1:30 duration298 words

Understanding the Product

Chip discusses the initial confusion he faced regarding Airbnb's product definition. He contrasts his background in hospitality with the tech-centric view of product, illustrating the importance of diverse perspectives in shaping a company's direction.

"Chip, thank you so much for being here and welcome to the podcast. Oh my god, Lenny. I I sort of feel like I'm your father who's so proud of his son has done. My son has done so well and I I like to t..."

4
6:00 - 8:00
2:00 duration372 words

Bridging Generational Gaps

Conley emphasizes the value of including older hosts in product discussions at Airbnb. He shares insights on how older perspectives can enhance understanding and communication within a predominantly younger team, fostering a more inclusive approach to product development.

"This was uh 13 years ago. This was I think it was the end of 2012 and then Brian called me and said, "Listen, we really want you to come in." And so I came in and gave a talk about innovation and hosp..."

5
8:00 - 10:00
2:00 duration387 words

The Importance of Humility

Chip reflects on the necessity of humility and humor while navigating the tech landscape. He discusses how acknowledging his limitations and respecting the expertise of younger colleagues helped him thrive in a challenging environment.

"mo many parts of the business definitely not the technical parts but I think the hardest thing for me is was just that initially when people were talking about product and Joe said you know I'm the ch..."

6
10:00 - 12:00
2:00 duration388 words

Learning from Brian Chesky

Conley shares his admiration for Brian Chesky's curiosity and willingness to learn. He recounts how Chesky's approach to leadership, including seeking advice from experts, influenced his own perspective on growth and collaboration.

"non-mobile and then went mobile. And then I was like, "Oh, wouldn't it be interesting if everything was mobile?" And at some point, I just said, "Listen, let's get some older people who are hosts in h..."

7
12:00 - 14:00
2:00 duration395 words

Challenges of Founder Mentality

Chip discusses the challenges posed by Chesky's founder mentality, including the expectation for others to match his work ethic. He highlights the importance of recognizing individual differences in work styles and the need for balance in a high-pressure environment.

"founder mode. It's not not as great to be working for someone in founder mode. Often a very challenging place to be. Yes. You reported to Brian. Uh also you were just your own boss basically your enti..."

8
14:00 - 16:00
2:00 duration347 words

Navigating the Tech Landscape

Conley reflects on the complexities of transitioning into the tech industry from hospitality. He shares insights on how his unique background contributed to his role at Airbnb and the importance of adapting to new environments.

"about Brian is he's been very honest in the last couple years on podcasts about his workcoholism and about the fact that the way he lives his life is not like other people. But back when I joined, you..."

9
15:35 - 17:10
1:34 duration312 words

Setting Unrealistic Goals

In this segment, Conley addresses the issue of setting unrealistic expectations within Airbnb, as Chesky believed that ambitious goals would drive performance. He explains how this approach could lead to stress among employees and the importance of emotional intelligence in leadership.

"demotivate people. And in Brian's case, I didn't have to deal with that too much because he didn't understand when I was starting. It was really I was in charge of the hosts around the world. And so q..."

10
17:10 - 18:08
0:58 duration156 words

Brian's Leadership Evolution

Chip Conley reflects on Brian Chesky's growth as a leader over time, comparing him to Steve Jobs. He acknowledges Chesky's generational leadership style and credits him for Airbnb's success while also noting the need for emotional intelligence in managing teams.

"is necessary because if you don't do that there's an almost an underlying message that people won't kick ass on their own. So there was a sense that Brian had that he had to maybe create ridiculous go..."

11
18:08 - 19:39
1:30 duration292 words

Effective Tactics for Working with Founders

Conley shares practical advice for effectively collaborating with founders in 'founder mode.' He emphasizes the importance of establishing clear intentions and alignment at the beginning of meetings to ensure productive discussions and mitigate potential conflicts.

"Having said that, I had to hold my tongue in meetings sometimes uh when I saw how he was operating because I wouldn't have done it that way. And I think over time, I hope I had a little bit of influen..."

12
19:39 - 21:09
1:29 duration286 words

The Value of Credibility and Customer Insight

In this segment, Conley discusses the significance of building credibility through direct customer engagement. He shares his experience of conducting a world tour to connect with Airbnb hosts, illustrating how firsthand insights can enhance one's authority and influence within a company.

"would do because that's something you can come back to over and over again during the rest of the meeting. When Brian or the founder, whomever it is, is beating you up on something, saying like, "Well..."

13
21:09 - 22:19
1:10 duration220 words

Intergenerational Collaboration in Tech

Conley introduces the concept of intergenerational collaboration in the workplace, particularly in tech. He explains the differences between younger and older brains, highlighting how their combined strengths can lead to innovative solutions and effective teamwork.

"so this whole story of you joining Airbnb in your 50s is a really good example of of uh c intergenerational collaboration, something that you're big on just the value of having folks that are older wo..."

14
22:19 - 23:11
0:51 duration147 words

The Benefits of Age Diversity

Chip Conley discusses the advantages of age diversity in teams, emphasizing how older individuals can provide holistic thinking and wisdom. He shares examples from his experience at Airbnb, illustrating how diverse perspectives can enhance problem-solving and creativity.

"you know when you have older brains connecting the dots thinking broadly peripherally younger team members being really fast and focused and being able to think linearly how to get things done. That c..."

15
23:11 - 24:41
1:29 duration308 words

Proactive Strategies for Regulation

Conley reflects on the importance of anticipating regulatory challenges in the hospitality industry. He shares insights on how Airbnb could have benefited from proactive strategies to address regulations, emphasizing the need for foresight in business planning.

"as uh noticeable quite frankly in some other diversities. Uh so I found that over and over was really helpful. Part of my job sometimes was to find the blind spot. You know, again, if you are very foc..."

16
24:41 - 26:00
1:19 duration249 words

Invisible Productivity and Mentorship

In this segment, Conley defines 'invisible productivity' as the ability to elevate others within a team. He shares personal anecdotes about mentoring younger colleagues and the impact of providing confidence and support in fostering their growth.

"been toxic in New York the whole for the last dozen years um ever since I was there. And there's a few other markets in the in the world where it was like that. So, I would just say, you know, um the ..."

17
26:00 - 27:03
1:02 duration207 words

The Role of Mentorship in Confidence Building

Conley discusses the essence of mentorship, using a personal story to illustrate how a mentor can serve as a confidant who instills confidence in younger professionals. He emphasizes the importance of asking questions to guide mentees toward their own success.

"and five other teams reporting to me. And I did my best to just be the kind of person who wasn't solving all the problems, but I was trying to elevate. There was a woman named Lisa Deost who is at at ..."

18
27:03 - 28:01
0:57 duration215 words

Addressing Ageism in Tech

Chip Conley addresses the reality of ageism in the tech industry, noting improvements over the past decade. He highlights the establishment of employee resource groups for older workers and the ongoing challenges faced by older professionals in a rapidly evolving job market.

"to success. So you're sharing a lot of really good examples of the value of older folks being within tech companies. So let me just ask you this. How how real is agism in tech? And I ask because a lot..."

19
28:01 - 29:19
1:18 duration211 words

AI and the Future of Work

Conley explores the implications of AI on the workforce, particularly regarding older workers. He discusses the potential for older professionals to leverage their wisdom and emotional intelligence in an AI-driven landscape, raising questions about the future of work.

"these senior we had these senior nomads come in and be like the voice of the customer for 10 weeks at Airbnb. And it was the wisdom at Airbnb older employee group that really actually pushed for this ..."

20
29:10 - 30:48
1:38 duration305 words

Navigating Midlife Transitions

Chip shares insights on how older professionals can navigate midlife transitions in their careers. He emphasizes the importance of being open to change, even if it means accepting a pay cut for a more flexible work schedule, and how this can benefit both the individual and the company.

"jury still out. There's a New York Times article that just came out about the question of is AI going to wipe out older people's jobs or younger people's jobs? And I think the answer is both. But the ..."

21
30:48 - 32:44
1:56 duration388 words

Curiosity as a Career Asset

Conley advocates for a 'mentor and intern' mindset, where older professionals maintain a sense of curiosity and engagement in their work. He explains how showing up with energy and a willingness to learn can help older individuals thrive in tech environments.

"that. That's a really interesting point that if you're older and you're maybe less connected to the most cutting edge ways of building and and coding, AI makes that a lot easier in many ways where you..."

22
32:44 - 34:56
2:12 duration429 words

Creating Intergenerational Collaboration

Chip discusses the importance of intergenerational collaboration in the workplace, highlighting mutual mentorship as a key strategy. He shares personal experiences of how older employees can support younger colleagues while also learning from them, fostering a culture of shared knowledge.

"well is I was very approachable. And over the course of time, the number of mentees I had, the number of people who just wanted to have coffee with me or tea, the number of people who just said, "Than..."

23
34:56 - 36:36
1:39 duration281 words

The Shift from Specialists to Generalists

Conley reflects on the evolving job market, emphasizing the growing importance of generalists over specialists in the age of AI. He advises hiring managers to look for candidates who demonstrate curiosity, passion, and problem-solving skills, which are essential in a rapidly changing tech landscape.

"to get started for free and get six months of the team plan. kod.io/lenny. Interestingly, curiosity comes up a lot when I ask AI forward people what are they focusing on helping their kids learn most...."

24
36:36 - 39:06
2:29 duration441 words

Articulating Experience in Job Applications

Chip offers practical advice for older job seekers on how to present their experience effectively. He suggests focusing on problem-solving skills and accomplishments rather than just job titles, encouraging candidates to articulate their unique value in a way that resonates with recruiters.

"important part of how effective companies think broadly. So I think that's a key one. I think also this idea of how do you create intergenerational collaboration in the form of mutual mentorships. Um,..."

25
39:06 - 43:15
4:08 duration779 words

From Business School to Hotel Empire

Conley shares his journey from business school to founding Joie de Vivre, the second-largest boutique hotel chain in the world. He reflects on the challenges and successes he faced along the way, illustrating how his experiences shaped his approach to leadership and mentorship.

"curiosity. If I was just the older elder dispensing wisdom, people would have gotten bored very quickly. And I think the fact Yeah. Yeah. I mean, I was on the board of Burning Man. Oh, that's cool. An..."

26
42:37 - 44:12
1:34 duration317 words

From Business School to Hotel Empire

Chip recounts his journey from business school to founding the second-largest boutique hotel chain in the world. He reflects on the initial challenges of starting a hotel and how a creative vision led him to transform a broken-down motel into a successful rock and roll hotel. This segment highlights the importance of passion and creativity in entrepreneurship.

"Yes. Um, speaking of throwing problems and also uh why Brian decided to reach out to you, I want to go back to the beginning of your career. Yes. So, you're good at this, by the way. You're good at th..."

27
44:12 - 45:02
0:50 duration164 words

The Near-Death Experience That Changed Everything

Chip Conley shares a life-altering near-death experience that reshaped his perspective on life and business. After suffering an allergic reaction that caused him to flatline multiple times, he emerged with a renewed appreciation for each day. This pivotal moment led him to sell his hotel company and embrace new opportunities, including his role at Airbnb.

"and I loved it till I hated it in my late 40s. I hated it. Didn't want to do it anymore. I was, you know, the Great Recession came along and it was just kicking my ass. And I really went through a bit..."

28
45:02 - 46:10
1:07 duration220 words

Lessons from a Life on the Edge

In this segment, Chip elaborates on the profound insights gained from his near-death experience. He describes vivid imagery and messages from the experience that emphasized the importance of slowing down to appreciate beauty and awe in life. This transformative event not only influenced his personal life but also his professional journey.

"there what happened there. Yeah, I was uh so I write books. have written seven or eight books and I had written a book called Peak uh how great companies get their mojo from Maslo and it was a book th..."

29
46:10 - 47:51
1:41 duration331 words

The Importance of Company Culture

Chip discusses the critical role of company culture in business success, particularly in distributed organizations like Airbnb. He explains how culture shapes decision-making and attracts the right talent, emphasizing that understanding a company's culture is essential for both employees and employers. This segment highlights the tangible impact of culture on organizational effectiveness.

"What? I did. You want to hear this? Yeah. No, I saw this beautiful stuff. the the best I think there's a hotel in San Francisco called the Vitali that I built um across the street from the ferry build..."

30
47:51 - 49:02
1:10 duration202 words

Navigating Remote Work Culture

Chip Conley addresses the challenges of maintaining a strong company culture in a remote work environment. He stresses the need for in-person gatherings to foster connections and ensure that employees understand the cultural cues that guide behavior. This segment provides practical insights for leaders managing distributed teams.

"So with building Juvary something you've written about a number of times is just the way you built it as a really unique approach to building a business. Specifically there's a huge focus on culture w..."

31
49:02 - 50:31
1:29 duration265 words

Culture Fit vs. Culture Add

In this insightful discussion, Chip differentiates between 'culture fit' and 'culture add.' He argues that while culture fit can sometimes exclude diversity, culture add encourages the inclusion of diverse perspectives that enhance the workplace. This segment explores how organizations can benefit from embracing diversity while maintaining a cohesive culture.

"the remote work world we live in, the more culture is important and more difficult because the when you're remote, you know, there's these few cues you have about how we do things around here and they..."

32
50:31 - 52:54
2:22 duration436 words

Understanding Company Culture in Interviews

Chip offers practical advice for job seekers on how to assess a company's culture during interviews. He suggests asking specific questions to gauge cultural alignment and emphasizes the importance of hearing consistent answers from multiple interviewers. This segment equips candidates with strategies to ensure they find a workplace that aligns with their values.

"language about culture fit. I like to say culture ad because culture fit to me means can actually be quite negative toward somebody who is the aberration. Um you have to fit in and especially if this ..."

33
52:54 - 54:29
1:35 duration268 words

The Peak Model: Hierarchies of Needs

Chip introduces the Peak Model, which applies Maslow's hierarchy of needs to employees, customers, and investors. He explains how understanding these needs can help organizations create environments that foster recognition and meaning. This segment highlights the significance of addressing both tangible and intangible aspects of employee satisfaction.

"certainly has an enormous oppressive uh influence, but uh you know you can you can you can be in a culture uh a really great culture of a team or a department in an overall company culture that's not ..."

34
54:29 - 56:02
1:32 duration279 words

Belonging Anywhere: Airbnb's Mission

In this segment, Chip discusses how Airbnb redefined its mission from home sharing to fostering a sense of belonging anywhere. He explains how this shift in perspective became a guiding principle for the company, influencing marketing strategies and host training. This insight showcases the power of aligning business goals with deeper human needs.

"simple. It's money or compensation at the base um recognition in the middle and meaning at the top. Now there are some industries and some kinds of jobs in which money is 90% of the pyramid. So just b..."

35
56:00 - 57:10
1:09 duration237 words

The Power of Meaning in Work

Conley highlights the significance of meaning in the workplace, especially in the context of AI and job offers. He explains how employees are increasingly valuing purpose over monetary compensation, illustrating the importance of a positive work environment and the impact of company culture on employee retention.

"becomes an organizing principle for how do you teach your hosts to create a sense of belonging? um how do our how does our marketing and advertising play up the belonging piece especially and the ever..."

36
57:10 - 58:01
0:51 duration175 words

Introducing the Modern Elder Academy

Chip Conley shares the inspiration behind the Modern Elder Academy (MEA), a school designed for midlife transitions. He explains the concept of a 'modern elder' as someone who balances curiosity with wisdom, and how MEA aims to help individuals navigate their purpose and personal evolution during midlife.

"Okay. So, you've had two major shifts in your career. You started the hotel chain, you went to then you went to Airbnb. Most recently, the Airbnb experience, I imagine, led you to starting something i..."

37
58:01 - 59:05
1:04 duration209 words

Transforming Aging Perspectives

Conley discusses the importance of reframing our relationship with aging, citing research that shows a positive mindset can lead to longer life. He emphasizes the need for wisdom management tools and how MEA provides a supportive environment for individuals to explore their purpose and redefine aging.

"now call it MEA because elder is a fraught word on some level. It makes you sound elderly. But um what I really wanted to create was a place where people could come and do a workshop. you you know the..."

38
59:05 - 1:00:14
1:08 duration197 words

The Upside of Aging

In this segment, Conley outlines the benefits of aging, including increased emotional intelligence and the ability to edit one's life priorities. He shares insights from his book 'Learning to Love Midlife,' aiming to shift the narrative around aging from negative to positive, highlighting the unexpected pleasures that come with growing older.

"biohack that's being done right now. So that's what we do. and we have 7,000 grads from 60 countries and 56 regional chapters around the world. So, it's a bit of a movement. And um I teach I I teach s..."

39
1:00:14 - 1:01:36
1:22 duration306 words

Midlife as a Chrysalis

Conley uses the metaphor of a chrysalis to describe midlife as a transformative period. He explains how individuals can experience a metamorphosis during this stage, liberating themselves from societal expectations and embracing personal freedom, ultimately leading to greater happiness in later years.

"Uh to your point I forget who said I think you said Jonathan has said this was the natural next step for you. I completely agree. It's like looking back this is the obvious thing you should be doing r..."

40
1:01:36 - 1:02:44
1:07 duration235 words

The U-Curve of Happiness

Chip Conley discusses the U-curve of happiness, which suggests that life satisfaction declines in midlife but increases again in later years. He shares insights on how individuals can navigate the midlife unraveling and emerge happier, emphasizing the importance of reframing expectations and embracing change.

"of view. Because when you actually have a pro-agging point of view, and you see the upside of aging, you take better care of yourself, both your mind and your body, you actually are willing to learn a..."

41
1:02:44 - 1:03:58
1:14 duration222 words

Anticipated Regret as Wisdom

Conley introduces the concept of anticipated regret as a catalyst for action in midlife. He encourages listeners to reflect on what they might regret not pursuing, using personal anecdotes to illustrate how this mindset can lead to meaningful life changes and a proactive approach to aging.

"happiness and it's been around for 20 years and it shows the following. It has changed in the last couple years because young adults are h unhappy like never before. So a 20 or a 22 year old really un..."

42
1:03:58 - 1:05:11
1:12 duration224 words

The Transformative Nature of Midlife

In this segment, Conley elaborates on the transformative aspects of midlife, likening it to a chrysalis phase. He discusses how individuals can embrace this period of change and emerge with a renewed sense of purpose and identity, challenging the negative connotations often associated with aging.

"you what a beautiful body looks like and you get some you're liberated into freedom in your 50s and beyond. And uh I can say that yeah, I'm happier today at 64 than I was at 47 when I was going throug..."

43
1:05:11 - 1:06:25
1:14 duration242 words

Embracing the Upsides of Aging

Conley shares various upsides to aging, including emotional intelligence and spiritual curiosity. He emphasizes the importance of integrating life experiences and wisdom, encouraging individuals to embrace their whole selves as they age and to recognize the growth that comes with time.

"sort of going through that not necessarily in this intense way yet but that might be You said there's a bunch of upsides to being getting older. It might be helpful just to share a couple of those thi..."

44
1:06:25 - 1:07:54
1:28 duration267 words

Who Should Join the Modern Elder Academy?

Conley outlines the target audience for the Modern Elder Academy, describing individuals in transition who seek to redefine their purpose. He highlights the diverse backgrounds of participants and the supportive environment MEA provides for personal growth and reinvention.

"There's a quote I found from you along these lines. The societal narrative on aging is just don't do it. Yeah. there. I mean, we sort of say like we want we don't want to age, but we do want to live. ..."

45
1:07:54 - 1:09:06
1:12 duration242 words

AI's Role in Creative Work

Chip Conley discusses how he utilizes AI tools like ChatGPT to enhance his writing process. He shares his workflow for generating blog content and how AI serves as a source of inspiration, allowing him to produce drafts quickly and efficiently.

"Those three. Yeah, that's the tagline. That's your tagline right there. Esselin meets Blue Zones meets what was the first one? The Four Seasons. The Four Seasons. Yeah. Nailed it. Okay, I'm going to z..."

46
1:10:02 - 1:11:49
1:47 duration354 words

The Equation of Despair

In this segment, Chip discusses his emotional equation: 'despair equals suffering minus meaning.' He elaborates on how increasing meaning in life can reduce despair, drawing from his experiences and insights on emotional well-being. This framework provides a valuable perspective on navigating life's challenges and finding purpose.

"weird idea and of course my not all my blog posts are so new age and and uh like that I I I write a lot on leadership but that was one that you know within you know 30 seconds I had a 250word you blog..."

47
1:11:49 - 1:13:00
1:11 duration238 words

Understanding Anxiety Through Equations

Chip introduces another emotional equation: 'anxiety equals uncertainty times powerlessness.' He explains how this formula helps individuals understand the sources of their anxiety and offers a practical exercise to manage it. This segment emphasizes the importance of clarity and control in reducing anxiety.

"to So there's a couple that are really interesting to me. This is you wrote about these in a book. You have a bunch of these equations about living a happier life. So the one you shared is despair equ..."

48
1:13:00 - 1:15:01
2:00 duration377 words

Favorite Life Lessons and Wisdom

Chip shares his favorite life motto: 'your painful life lessons are the raw material for your future wisdom.' He reflects on how challenges contribute to personal growth and wisdom, reinforcing the idea that adversity can lead to valuable insights. This segment encourages listeners to embrace their struggles as part of their journey.

"And when you take free floating anxiety and put it into uh a an equation, it actually makes it more tangible and you often are less anxious as a result. Boom. Okay. So, if you're feeling anxious right..."

49
1:15:01 - 1:17:00
1:59 duration379 words

Behind the Scenes of Burning Man

In this segment, Chip reveals lesser-known insights about Burning Man, including the existence of Fly Ranch, a contrasting environment to the festival. He describes Fly Ranch's natural beauty and its significance, providing a unique perspective on the culture surrounding Burning Man. This discussion highlights the diversity of experiences within the Burning Man community.

"often come back to and find really useful in work or in life? I imagine you have many, but is there one that comes to mind? I mean, my favorite one right now is your painful life lessons are the raw m..."

50
1:17:00 - 1:19:09
2:09 duration417 words

Connecting with Chip Conley

Chip Conley shares where listeners can find him online, including his website and social media presence. He emphasizes the importance of wisdom and invites the audience to explore free resources available on the Modern Elder Academy website. This segment serves as a call to action for those interested in personal growth and wisdom.

"It didn't. Yes. Chip, two final questions. Where can folks find you online and how can listeners be useful to you? So online, meowisdom.com is the website for MEA. My website's chipconley.com, co- ny...."