Let’s flip the script.
When I left the hotel business to become a “modern elder,” I was terrified. First of all, I disappointed a lot of people who didn’t want me to change my identity as the founder and CEO of my boutique hotel company. People are threatened by your change because it may mean they have to change.
And, then, what if I failed in this new role at Airbnb? I felt like such an imposter leading hospitality and strategy for a tech company when I didn’t understand any of the tech lingo. And, I was twice the age of seemingly everyone in the company. A geezer amongst geeks.
We live in a culture that’s allergic to mistakes. But mistakes are fertile ground—they’re the mulch from which wisdom grows. Neuroscience tells us we learn more from errors than successes. And most personal breakthroughs—whether in relationships, careers, or identity—come after we risk being misunderstood or misjudged.
Here’s an idea: intentionally make a “beautiful mistake.” Try something that stretches you, even if it doesn’t fit others’ expectations. Start painting. Move to Portugal. Launch that podcast (I’m sure I’ll make lots of mistakes on The Midlife Chrysalis – a new episode just dropped today). Say no. Say yes. Let someone down who was holding you back from your own evolution.
At MEA, we talk about the U-Curve of happiness—how life satisfaction dips in midlife but rises after. Part of the climb back up? Shedding the need for perfection and applause.
So this week, go make a mistake. Be a disappointment. Show your humanity. Then pay attention to what’s left standing after the people-pleasing dust settles. That’s probably your soul saying, “Finally.”
Welcome to the freedom of your second adulthood.
-Chip