Tapping Wisdom at All Ages

In his upcoming book, Wisdom @ Work: The Making of a Modern Elder, best-selling author, hospitality entrepreneur, and self-described business rebel Chip Conley challenges us to liberate “elder” from the word “elderly” and rethink life after 50. He captures his own experience coming out of “retirement” after serving as founder of the boutique hotel brand Joie de Vivre to join as an advisor/intern for the then-tech start-up Airbnb.

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What follows is our conversation with Chip, who also serves as an Esalen trustee, on what it means to have five generations in the workplace today and how age really can be just a number.

Esalen News: Chip, many of us know you from your book PEAK: How Great Companies Get Their Mojo from Maslow. Did Esalen or Abraham Maslow play a part at all in your new book on the modern elder?

What was definitely at play here was the idea that from the time of the 60s it’s become clear that wisdom can move both ways. Esalen was able to prove that in its early years. Having read Abe Maslow’s diaries, I know he was fascinated by how much he could learn from younger people at Esalen as well as how much he could teach them. From everything I’ve read on Maslow there was a mutual mentorship happening between him and the young people at that time at Esalen.

Esalen News: You share that this book was the manifesto you wished you had when you joined Airbnb as an advisor. What do you think you got right then, and what would you have done differently?

The thing I would have done differently was to have been less naïve about joining a tech company for the first time in my life. There was a glossary of terms I needed to study the first day. What I did well was to shift to a place of thinking “Well…I have to be a mentor and intern at the same time”. This is the art of mentoring privately and interning publically. Many of us Boomers had decades to become fully baked leaders, whereas Millennials have had to microwave their leadership skills as power is granted to them so quickly today due to our growing digital reliance. So I would ask questions and be humble in public and then move from “sage on the stage” to “guide on the side” for mentoring.

Esalen News: What do you think are the most common misconceptions Boomers have of Millennials and Millennials of Boomers?

Stereotypes such as Boomers being technophobes and Millennials being terrible with emotions may not be true on an individual basis, but I do believe as people live longer on the planet they improve their emotional intelligence, or EQ. We have an opportunity to collaborate and exchange EQ for DQ, or digital intelligence, and we can do this by understanding each other better.

There’s a Mark Twain quote about age and mind over matter, and that if you don’t mind your age, it doesn’t matter. We all have the capacity to be a perennial—someone who is constantly blooming. It calls to mind the story of Satchel Paige who was a rookie baseball player and didn’t know his real age. So the owner of the Cleveland Indians went down to Mobile, Alabama, to get this player’s birth certificate only to discover Paige was 42. What would life be like if we didn’t know our age?
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‍Esalen News: What is the impact on an organization if we can successfully create collaboration across generations?

I believe intergenerational collaboration, virgin territory in many companies, could become the ultimate disrupter. I had led multigenerational teams at Joie de Vivre, and I learned that an aligned and empowered team is like a crew rowing in unison. When you tap into the diversity of personality types and perspective across generations, it’s similar to what happens when the crew is stroking as a unified body—rather than a group of individual rowers—at just the right pace. Rowers call this miracle of physics “swing,” and it allows the elevated boat to move more quickly since there is less friction in the water holding it back. A key to this is articulating the mission and purpose of the organization—a shared mission reduces friction. It also helps people elevate themselves beyond petty grievances that people tend to have in most organizations. When people sense meaning and impact of their work, they are going to do what supports the mission.

Esalen News: You share your personal experience with the U curve of happiness—a concept that our happiness can see a dip in our 40s and then begin to edge back up again. Is part of the attribute of a modern elder the ability to rethink the pursuit of happiness?

Many people think that when they have success they will have happiness. Yet there are an awful lot of studies that show happiness drives success more so than success driving happiness. The key is to get clear on your metrics.

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In my TED Talk I asked how do we start to bring the idea of meaning into our work and make it more tangible? One way is to identify the role models we admire and determine what was it that gave them the motivation and inspiration to pour energy in their work the way they did. Few of them did it primarily because of money. I think money is an important ingredient to having less stress, but I think that at some point we aspire towards meaning over money and recognition over time.

Esalen News: This January you launched the Modern Elder Academy in El Pescadero, Baja California Sur (Mexico) based on principles you’ve outlined in your book. What are your plans for the academy? What kind of wisdom do you hope your students will walk away with (or tap into)?

The Academy has probably more to do with Esalen than my book does. In a sense it takes my boutique hotel background and my fascination for personal growth and for Esalen and uses those two ingredients to create a new way of passage into midlife. We have a curriculum, and not just a facility, for a specific demographic. We recognize people in midlife are going through transitions and so much of this is private.

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Historically we’ve created rituals and celebrations in transitional times—bar mitzvahs, weddings, and baby showers. There is a whole period of middle life that is without educational components to understand what we’re going through or rites and passages to help lead the way. We just finished the beta program of the academy which, for our two-week Immersion group, included a vision quest in the desert. We will open to the public in November.

Esalen News: Speaking of wisdom, when was the last time someone shared some words of wisdom with you and what was it?

My dad is 80 and we recently went on a diving trip to Indonesia. He was saying to me that he doesn’t feel 80 and doesn’t think like he’s 80. I asked him how long he thought he’d live to be and he replied 98.

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We started to do the math: if adult life started at 18, and he lives to 98, and he is now 80 years old, he is completed 62 of 80 adult years. I told him you’re barely in the fourth quarter of adult life. He said, “Yeah, here I am at 80, and I just learned about Buddhism and continue to learn new places to scuba dive. My life is far from over.”

Just when you think you’re not in space to do it, you can become a beginner again. I feel lucky to have been able to be involved with Esalen in so many different ways and apply that learning at the Academy.

Wisdom @ Work will be published September 18.

Photos courtesy of Chip Conley.