Proud Like a Papa.


The words “encore” and “mentor” sound alike. I was 52 years old in early 2013 and had no idea what was next for me. In the movie “The Intern,” Robert DeNiro says, “Musicians don’t retire. They quit when there’s no more music inside of them.” I know I still had music to share, but I wasn’t sure with whom to share it.

You know my story. The three co-founders of Airbnb approached me, and I spent four full-time years there and three and a half years as a strategic advisor (mostly to Brian Chesky, the co-founder and CEO). Of course, you don’t know what advice will “land” with a mentee, especially when they’re 21 years younger and also your boss.

I loved watching this brief interview clip of my friend and author Simon Sinek interviewing Brian because it reaffirmed I’d had an impact for the following reasons (expressed in this clip):

  • Mindset is essential and it creates a “collective consciousness.”
  • Look for moments when innovation is essential and the org is primed to be open to it.
  • Be curious. Wisdom is more important than knowledge.
  • Be a “receiver of ideas.” Knowledge speaks and wisdom listens (thanks, Jimi Hendrix).
  • Don’t be embarrassed by a pivot. It’s part of what it means to be agile.
  • Operating in the “survival” mode isn’t fun. Use the PEAK pyramid to focus on transformation.
  • Don’t let your amygdala hijack you. Be conscious of your emotions. Leaders’ emotions are contagious.

In sum, your role as a Modern Elder isn’t to force a mentee into your way of thinking. But you may want to size-them-up in advance to make sure they’re open to your point of view. If there’s fertile ground for them to learn, and you’re humble enough to realize you’ll learn from them, you’ll feel like I did today when I watched this clip (or the time when Brian and I were on stage at the Commonwealth Club together).

Neither Brian nor I are perfect, and we’re quite different from each other in many ways. But I know I had an impact. As Erik Erikson suggested, “I am what survives me.” That’s true of a parent. And that’s true of a mentor.

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