Brian Chesky's secret mentor who died 9 times, started the Burning Man board, and built the world's first midlife wisdom school | Chip Conley (founder of MEA)
Chip Conley, founder of MEA and former Airbnb "Modern Elder," discusses thriving in tech as you age, working with Brian Chesky, building company culture, and how a near-death experience led him to create the world's first midlife wisdom school.
Deep Dive Analysis
13 Topic Outline
Joining Airbnb in Midlife and Initial Challenges
Working with Brian Chesky and Founder Mode Dynamics
Value of Intergenerational Collaboration in Tech
Addressing Ageism and Thriving as an Older Professional
Founding Joie de Vivre Hotels and Early Career
Life-Changing Near-Death Experience and Its Impact
Importance of Company Culture and Interviewing for Fit
Applying Maslow's Hierarchy to Employees and Customers
Introduction to the Modern Elder Academy (MEA)
The Upside of Aging and the U-Curve of Happiness
Leveraging AI for Creative Work and Blogging
Recommended Books and Emotional Equations
Insights on Burning Man's Fly Ranch
10 Key Concepts
Product (in Tech)
In the tech industry, 'product' refers to the software, app, or digital experience, distinct from the physical goods or services (like homes in Airbnb's case) that the platform facilitates. This distinction highlights a common misunderstanding for those new to tech.
Fluid Intelligence
Associated with younger brains, fluid intelligence is characterized by speed, focus, and proficiency in problem-solving and linear thinking. It's excellent for quickly grasping new concepts and executing tasks efficiently.
Crystallized Intelligence
Associated with older brains, crystallized intelligence involves holistic and systemic thinking, connecting disparate ideas, and recognizing patterns. It allows for broader perspectives and a deeper understanding of complex situations.
Invisible Productivity
This concept describes the value of a manager or team member who elevates the performance of everyone around them, making others better rather than solely focusing on their individual output. It's about fostering growth and maximizing collective talent.
Culture Ad vs. Culture Fit
While 'culture fit' can imply conforming to existing norms and potentially exclude diverse perspectives, 'culture ad' suggests that new team members bring unique qualities that enrich and expand the company's culture. This shift in mindset values diversity as an asset.
Modern Elder
A modern elder is defined as someone who is as curious as they are wise. They embody a blend of experience and a continuous appetite for learning, making them valuable mentors and contributors in dynamic environments.
Midlife Chrysalis
This metaphor describes midlife as a period of profound transformation, akin to a caterpillar's journey in a cocoon before becoming a butterfly. It reframes midlife as an opportunity for metamorphosis and reinvention, rather than a crisis.
Anticipated Regret
A form of wisdom that acts as a catalyst for action. By considering what one might regret not learning or doing in the future, individuals are motivated to pursue new experiences or skills in the present.
U-Curve of Happiness
A global phenomenon indicating that life satisfaction generally declines from the early 20s, bottoms out between ages 45 and 50, and then steadily increases, with people reporting greater happiness in their 50s, 60s, 70s, and beyond compared to their midlife years.
Wisdom
Defined as metabolized experience, mindfully shared for the common good. It suggests that wisdom is not merely accumulated knowledge but experience that has been processed, understood, and then generously offered to benefit others.
14 Questions Answered
Chip joined Airbnb at 52, where the average age was 26, requiring him to be both wise and curious, often feeling like the 'dumbest person in the room' due to unfamiliar tech lingo and reporting to a CEO 21 years his junior.
Working for Brian Chesky in founder mode was challenging due to Brian's expectation that everyone would match his intense pace and duration, his strong belief in his own product vision (like Steve Jobs), and his tendency to set unrealistic goals, which created stress for teams.
To be effective, it's crucial to establish clear alignment on intentions, success metrics, and meeting goals upfront. Building credibility through deep customer understanding and limiting reliance on rigid presentations can also help navigate combustible founder personalities.
Intergenerational collaboration is brilliant because it combines the fluid intelligence of younger team members (fast, focused problem-solving) with the crystallized intelligence of older members (holistic thinking, connecting dots), leading to comprehensive and effective solutions.
Ageism is a real problem in tech, where older workers can be perceived as expensive and slow, especially with rapidly evolving technical skills. However, the rise of AI might favor older managers with emotional intelligence, pattern recognition, and wisdom, as AI handles technical tasks.
Older professionals can thrive by showing up with voracious curiosity, passionate engagement, and positive energy, acting as both a learner and a teacher. Being approachable, providing support to younger colleagues, and demonstrating 'invisible productivity' are also key.
Hiring managers should seek generalists who can think broadly, as AI accelerates the need for such skills. They should also look for candidates who are passionate, curious learners with good energy, and consider creating mutual mentorships within the organization.
Company culture is crucial because it dictates 'what happens around here when the boss is not around,' guiding employee decisions and attracting the right talent. In remote settings, it's even more vital, requiring intentional in-person gatherings to reinforce shared norms.
Job seekers should actively interview the company by asking questions like, 'What are three to five adjectives that define this culture?' and 'What's the biggest problem in this culture?' Comparing answers from multiple interviewers can reveal cultural alignment or misalignment.
Based on Maslow's hierarchy, the employee model consists of compensation at the base, recognition in the middle, and meaning at the top. While money is foundational, differentiation and employee satisfaction often come from recognition and a sense of purpose.
Shifting your mindset on aging from negative to positive can lead to significant benefits, including an average of 7.5 years of additional life. A pro-aging perspective encourages better self-care, a willingness to learn new things, and a focus on the unexpected pleasures of getting older.
The U-curve of happiness describes a global pattern where life satisfaction tends to decline from the early twenties, reaching its lowest point between 45 and 50, and then steadily increases into older age, with people often being happier in their 50s, 60s, and beyond than in their 40s.
AI, specifically tools like ChatGPT, can serve as a valuable source of inspiration and help generate first drafts for creative writing tasks like daily blog posts. It can quickly produce content based on a prompt, which can then be adapted and refined by the writer.
A lesser-known aspect of Burning Man is its ownership of Fly Ranch, a 3,400-acre property about 10 miles from the main event site. Unlike the alkaline desert of Burning Man, Fly Ranch is a lush, porous landscape with hot springs, hot pools, and wildlife, offering a contrasting natural experience outside of the event period.
26 Actionable Insights
1. Shift to Positive Aging Mindset
Adopt a positive mindset towards aging, viewing it as an upside rather than a decline, as this shift has been shown to add 7.5 years to life by encouraging better self-care and openness to new experiences.
2. Increase Meaning to Reduce Despair
Understand that despair equals suffering minus meaning; therefore, to reduce despair, focus on increasing meaning in your life, as suffering is often a constant.
3. Address Anxiety with Balance Sheet
To reduce anxiety, which stems from uncertainty and powerlessness, create an ‘anxiety balance sheet’ with four columns (what you know, don’t know, can control, can’t control) to make it tangible and less overwhelming.
4. Use Anticipated Regret as Catalyst
Ask yourself, ‘10 years from now, what will I regret if I don’t learn or do it now?’ to use anticipated regret as a form of wisdom and a catalyst for taking action and trying new things as you age.
5. Maintain Curiosity and Passionate Engagement
For those in midlife in tech, show up with curiosity and passionate engagement for your work, as your energy will be more noticeable than your age.
6. Project Positive and Youthful Energy
Show up with both physical energy (not resting on laurels) and positive energy, aiming for the kind of vitality seen in people 10-20 years younger, to be perceived as ‘age fluid’ and approachable.
7. Cultivate Humility and Curiosity
Be both wise and curious, and don’t be afraid to be the ‘dumbest person in the room,’ as this requires humility and fosters learning.
8. Practice Humility and Respect
Don’t pretend to know things you don’t, maintain a sense of humor and humility, and show respect to others to foster a collaborative environment.
9. Transform Painful Lessons into Wisdom
Recognize that challenging or painful life lessons are the raw material for your future wisdom, meaning difficult times contribute to valuable personal growth.
10. Establish Meeting Alignment Upfront
Before presenting to a founder or in any meeting, clearly state the intention, define success, and what you aim to accomplish to ensure alignment and provide a reference point if the conversation deviates.
11. Craft a Problem-Solving Resume
Instead of just listing roles and bullet points, articulate your accomplishments by describing a thorny problem you faced, the skills you used to solve it, and the result, using this as a conversation piece in interviews.
12. Interview the Company’s Culture
When interviewing, ask multiple people about 3-5 adjectives defining the culture and its biggest endemic problems, and observe if responses align to assess cultural fit and potential influence.
13. Prioritize In-Person Gatherings
For remote or distributed teams, prioritize more frequent in-person gatherings to reinforce culture and provide cues on ‘how we do things around here,’ which are harder to convey virtually.
14. Develop Generalist Skills
Focus on developing generalist skills and the ability to think broadly, as AI accelerates the shift from specialists to generalists, making broad thinkers increasingly important.
15. Foster Mutual Mentorships
Seek out and create mutual mentorships where both parties teach and learn from each other, bridging generational gaps and fostering intergenerational collaboration.
16. Consider Reduced Hours for Value
If you’re an older professional (45+) and financially stable, consider taking a pay cut for reduced hours (e.g., 60-80% time) to continue contributing valuable institutional wisdom and process knowledge to a company.
17. Limit Detailed Presentation Reliance
Be cautious about being overly reliant on detailed presentation decks, especially with ‘combustible founders,’ as meetings can go off-path; use decks primarily to set principles and goals at the start.
18. Be Approachable and Positive
Be approachable and maintain a positive demeanor in meetings and interactions, as this draws people to you and fosters a supportive environment.
19. Be a Confidant (Confidence Giver)
Act as a confidant by asking questions that help younger mentees find their roadmap to success, thereby giving them confidence.
20. Cultivate and Share Experience
Actively metabolize your life experiences and mindfully share them for the common good, as this process defines and builds wisdom.
21. Ask ‘How Can I Help?’
When interviewing, ask the interviewer, ‘What’s the biggest problem you’re dealing with here? And how can I help you?’ to show initiative and problem-solving orientation.
22. Assess Culture for ‘Add’
Before taking a job, thoroughly understand the company’s culture to ensure it’s one you can thrive in and potentially add to, rather than just ‘fit’ into, which can be exclusionary.
23. Understand Employee Motivation Hierarchy
Recognize that employee motivation follows a hierarchy: compensation at the base, recognition in the middle, and meaning at the top, with meaning often being the differentiator.
24. Apply Customer Needs Hierarchy
Understand customer needs as a hierarchy: meeting basic expectations, then desires, and finally, identifying and meeting unrecognized needs to create exceptional value.
25. Use AI for Creative Drafts
Leverage AI tools like ChatGPT to generate first drafts for creative writing tasks, especially when inspiration is low or deadlines are tight, then adapt the output.
26. Utilize Free Wisdom Resources
Access free resources on the MEA website, such as ‘Why Successful Leaders Value Wisdom’ and ‘The Anatomy of a Transition,’ to develop transitional intelligence (TQ) and wisdom, which are crucial modern skills.
8 Key Quotes
I had to be both wise and curious and often the dumbest person in the room.
Chip Conley
It's great to be in founder mode. It's not as great to be working for someone in founder mode.
Chip Conley
When you have older brains connecting the dots, younger team members being really fast and focused, it's brilliant.
Chip Conley
People won't notice your wrinkles as much as they'll notice your energy.
Chip Conley
Midlife is not crisis.
Chip Conley
Culture is what happens around here when the boss is not around.
Chip Conley
Your painful life lessons are the raw material for your future wisdom.
Chip Conley
We sort of say we don't want to age, but we do want to live. And quite frankly, aging and living are the same thing as are aging and growing.
Chip Conley
1 Protocols
Anxiety Balance Sheet
Chip Conley- Create four columns for your free-floating anxiety.
- In the first column, list 'What is it you do know about the thing that's making you anxious?'
- In the second column, list 'What is it you don't know?'
- In the third column, list 'What is it you can control or influence?'
- In the fourth column, list 'What is it you can't control or influence?'