How to Manufacture Luck
On serendipity, midlife renewal, and the quiet courage to begin again.
When Chip Conley sold a majority stake in his boutique hotel company, Joie de Vivre, in 2010, he was 49 and ready for a quieter life. Two decades of success had brought him wealth, respect—and exhaustion. But three years later, a call from Brian Chesky, the young CEO of Airbnb, changed everything.
Chesky asked if Chip would mentor him and help the company grow up without losing its soul. By then, Chip was 52—twice the age of most Airbnb employees, from an entirely different industry, walking into a tech culture obsessed with youth. Yet he said yes.
That yes became a hinge moment. It sparked his next chapter and, eventually, the founding of the Modern Elder Academy—a place dedicated to reframing midlife as a time of renewal, not decline. Years later, when I found myself in my forties navigating my own questions about meaning and change, I spent time there as an intern and later a fellow. What I witnessed in that desert community in Baja wasn’t luck in the lottery sense—it was something quieter and more intentional.
Chip and the people around him seemed to manufacture luck through presence, generosity, and openness. They noticed opportunities others overlooked. They acted before they felt fully ready. They created space for surprise.
The Inner Science of Serendipity
Psychologist Richard Wiseman calls this luck readiness—a mindset that turns uncertainty into opportunity. His research shows that so-called “lucky” people share three habits: they’re curious about the unfamiliar, attuned to subtle cues, and quick to reframe setbacks as openings.
Luck, it turns out, is a pattern of awareness. It’s less about what happens to us and more about what we’re able to notice. When our minds are rigid or overplanned, life has no room to intervene. When we loosen our grip, our field of vision widens—and we begin to catch the threads of meaning that are already there.
That’s what I saw in Chip. He didn’t stumble into a second act; he created the conditions for it to find him. His curiosity, humility, and willingness to keep learning made him magnetic to new possibilities. He didn’t chase luck—he invited it.
A Micropractice for Everyday Serendipity
Before your next meeting or conversation, pause and ask:
“What might I learn here that I don’t yet know I need?”
Then pay attention—to what’s said and unsaid. Notice small coincidences, repeated themes, or people who seem to appear at just the right moment. Serendipity often whispers before it knocks.
Where to Practice It
On your commute, look up instead of scrolling.
Over coffee, talk to the person you usually pass by.
When plans change, ask, “What is this space making room for?”
Each pause is an opening. Every moment, a potential invitation.
The Small Openings That Find Us
Luck, at its deepest level, is participation. It’s saying yes to life before knowing where it will lead.
Perhaps that’s the quiet truth Chip embodies—and what I felt during my time at the Academy: luck begins when we stop trying to control the story and start staying awake to it.
Meaning rarely arrives all at once. It grows quietly, when we begin to listen.