Lessons from Chip Conley on building a midlife career of meaning and relevance

By Michael Melcher
Partner, Next Step Partners

New York Times Bestselling author and mentor to Airbnb’s CEO in conversation with Michael Melcher on his Career Stewardship podcast

We used to think of careers in three stages. We would learn up to age 25, earn until age 65 and then retire until we die. Life today isn’t so linear.

After selling the company he started as a rebel entrepreneur at age 26, Joie de Vivre Hospitality, Chip Conley wasn’t sure what was next. He could have retired at age 52. But the young founders of Airbnb came calling. He served as Airbnb’s Head of Global Hospitality & Strategy for four years — while also being CEO Brian Chesky’s mentor — and continues today as a Strategic Advisor to the company’s leadership.

In Episode 11 of my Career Stewardship podcast, Chip Conley tells me that he thought his role at Airbnb would be to share his insights on leadership, entrepreneurship and the hospitality business. He discovered what they really needed was something else. Something that grows with age: emotional intelligence.

Intergenerational workplaces

Chip says, “We’re living with five generations in the workplace for the first time. I like to think of it as an intergenerational potluck where we each bring to the table what we do best. And often what we do best has a generational component to it.”

His alliance with the Airbnb team meant that his younger colleagues brought digital intelligence, while Chip brought emotional intelligence. “The EQ of emotional intelligence showed up in all kinds of different ways,” says Chip. “Everything from how to run a good meeting, to how to give a great performance review that actually sticks and inspires greatness, to really understanding how to build relationships with competitors.” 

Responsibility for relevance

Chip goes on to discuss the responsibility for relevance and how important it is to understand the context to know how to deliver your wisdom.

“Having been a long time brick and mortar hotelier, all of the sudden in a tech company focusing on disrupting the hospitality business, a lot of my knowledge and mindset was really not all that helpful at Airbnb. I needed to know what I needed to let go of and then what of my wisdom and knowledge was valuable here. 

“Once I understood the relevance of what was important, I had a lot to offer. But if I took a blunt instrument and sat everyone down and said let me tell you about how the hospitality industry works and I went on for an hour talking about the history of the industry … no one would have wanted to hang out with me or listen to me.” 

To help others fine-tune their relevance in midlife, in 2018 he co-founded The Modern Elder Academy, a fascinating place devoted not so much to lifelong learning but rather to “long-life learning.”

Chip Conley’s career advice 

Over the course of our 30 minute conversation, Chip and I discuss building careers of relevance and meaning at all stages of life –and it’s an episode full of golden nuggets, including:

  • Navigating career transitions: learning to cultivate and repurpose what you’ve learned
  • Building intergenerational alliances where wisdom flows in both directions
  • The shift from a “proving” mindset to an “improving” mindset
  • How the Modern Elder Academy focuses on engendering a mindset of curiosity and learning
  • Cultivating learning: what Chip has been writing in his “Wisdom Book” every week over the past 32 years
  • Chip’s favorite book of all time and its central lesson

About the Career Stewardship with Michael Melcher podcast

This 20 episode podcast from career expert, Michael Melcher, will help you figure out what to do about your career during lockdown and beyond. Each episode offers best practices, stories from the field, and bite-sized tips to help build your career success in both the short and long term. 

As one of the partners at Next Step Partners, Michael is a seasoned expert on developing leaders and helping senior professionals make career transitions. A former lawyer, foreign service officer and startup CEO, he has navigated several career transitions himself.

Subscribe to Career Stewardship with Michael Melcher on Apple Podcasts, Spotify, Stitcher, Google Podcast or your favorite platform. You can find additional resources on the show website:

About Chip Conley

New York Times bestselling author Chip Conley is the hospitality maverick who helped Airbnb’s founders turn their fast-growing tech start-up into a global hospitality brand. In Wisdom@Work: The Making of a Modern Elder he shares his unexpected journey at midlife — from CEO to intern — learning about technology as Airbnb’s Head of Global Hospitality and Strategy, while also mentoring CEO Brian Chesky. Chip is the founder of the Modern Elder Academy, a school dedicated to helping people navigate midlife. He serves on the board of and the advisory board for the Stanford Center for Longevity.




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