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)

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.