“When you create an environment where you have a mixture of ages, just like a mixture of genders and a mixture of races, you create a better workplace and more effective teams.” – Chip Conley

In our increasingly accelerated world that venerates the young, many in mid-career sense that the ground is shifting beneath their feet, leaving them feeling invisible, undervalued, and threatened by the digital natives nipping at their heels. However, today’s guest on Finding Brave argues that experience is on the brink of a comeback.

Rebel hospitality entrepreneur and New York Times bestselling author, Chip Conley disrupted his favorite industry… twice. At age 26, he founded Joie de Vivre Hospitality (JdV), transforming an inner-city motel into the second largest boutique hotel brand in America. He sold JdV after running it as CEO for 24 years, and soon the young founders of Airbnb asked him to help transform their promising start-up into the world’s leading hospitality brand. Chip served as Airbnb’s Head of Global Hospitality and Strategy for four years and today acts as the company’s Strategic Advisor for Hospitality and Leadership. His five books have made him a leading authority at the intersection of psychology and business. Chip was awarded “Most Innovative CEO” by the San Francisco Business Times, is the recipient of hospitality’s highest honor, the Pioneer Award, and holds a BA and MBA from Stanford University.

In this episode, he tackles the hard truth that ageism is as big an issue in the working world as any other bias. In the process, Conley liberates the term “elder” from the stigma of “elderly” and ignites a conversation for society to embrace age like any other diversity while also celebrating the value of wisdom and experience.

Highlights from this Episode:

  • The impact two particular authors have had on Chip and how he draws on them for inspiration in his own work [3:40]
  • The way he has turned despair into an equation [4:22]
  • What Chip has come to realize about the need for transitions in life and why they’re so hard for us to navigate through [6:12]
  • What’s really going on with ageism in today’s society and the role that technology is playing [10:25]
  • The tremendous opportunity available now for baby boomers and why Chip says the “pendulum is swinging” [11:42]
  • The advantages of creating a work environment with a mixture of ages [15:37]
  • Who his new book is for and what it will show the reader about wisdom at work [16:42]
  • Why Chip has always been humble in learning and how he became an intern in Silicon valley while mentoring others privately [26:40]
  • The difference between the modern elder versus a traditional one [28:38]
  • Why modern elders need to recognize their strengths and be confident in their work environments [33:08]

For more information:






Resources Mentioned:

Chip’s New Book, Wisdom @ Work: The Making of a Modern Elder and his Previous Works

Modern Elder Academy

Man’s Search for Meaning The Classic Tribute to Hope from the Holocaust by Viktor E. Frankl

Paul Tasner’s TED Talk, How I Became An Entrepreneur at 66

Mindset: The New Psychology of Success by Carol Dweck

Kathy’s Forbes Interview with Donna Hicks, How To Build A Culture Of Dignity, And What Happens If You Don’t


“I really appreciate that the intersection of psychology and business can be a complex one.” [3:46]

“I was able to realize that if on a weekly basis I just made an inventory of all the things that gave me meaning this week, that focus on the meaning helped reduce the despair.” [5:11]

“So we need to figure out how to address the fact that this is a period of life that has all kinds of transitions, and we have not figured out how to provide the rites of passage for that.” [7:29]

“If digital intelligence is the defining characteristic of what most companies are looking for, who is the most digitally savvy out there? It’s the digital natives…” [11:17]

“There’s more and more evidence out there that going out and doing it on your own is not something that is just meant for 20-year-old hoodie wearing boys.” [26:24]

“I’ve always had a fascination with creating things that people wanted. I wanted to make people happy.” [28:18]

“That’s what you thought you had to be as a young person in Silicon Valley;  you had to be the smartest person in the room. I was proving you could be the dumbest person in the room and still be extremely valuable.” [30:28]

“I think the bottom line is that the idea of a modern elder is that you are curious and wise at the same time.” [31:39]

“We are hopefully growing whole more than we are growing old.” [37:30]

Sponsor Highlight!  

I’m thrilled to share that Audible.com is a sponsor of Finding Brave! Take advantage of their great special offer of one FREE book of your choice with a 30-day FREE membership trial! And feel free to keep the book even if you cancel the membership. Click here to sign up for your free book! http://www.audibletrial.com/FindingBrave

Watch the video of this episode!
Now you can experience each Finding Brave episode in both audio and video formats! Check out new and recent episodes on my Youtube channel at YouTube.com/kathycaprino. And please leave us a comment and a thumbs up if you like the show!




  1. 45: The Future of Work and Staying Competitive, with Alexandra Levit - […] Episode 38: Embracing Your Age and Wisdom – The Making of a Modern Elder, with Chip Conley […]


Kathy’s new book The Most Powerful You: 7 Bravery-Boosting Paths to Career Bliss shares vital information on the 7 most damaging power gaps that 98% of professional women face and how to overcome them. Boost your power and confidence today!


Best Career Coaches 2020