The barriers to entry are low. The barriers to endurance? Sky high.
Every era of entrepreneurship has its storms, but lately it feels like we’re living through a perfect storm layered on top of a hurricane wrapped in an earthquake.
I’ve had a front-row seat to this reality more than once.
At Joie de Vivre Hospitality, I navigated two once-in-a-lifetime downturns back-to-back: the dot-com bust and September 11 attacks, followed just a few years later by the Great Recession. Just when you think you’ve earned your resilience badge, the universe hands you another test.
Then came my “modern elder” time at Airbnb, where the headwinds weren’t just economic—they were existential. Regulatory battles. Trust issues. Skepticism about whether this “home-sharing thing” would even survive.
And then, with Modern Elder Academy, the hits got more personal and more global at the same time: Covid shutting down travel, my own cancer diagnosis, and a major leadership reorganization—all while trying to build something that had never quite existed before.
But here’s the thing: the past year may have taken the cake.
Tariffs.
A near stock market crash.
A Mexico cartel war (that, frankly, has had no impact on Baja where our campus is; it’s as safe as ever, but the fear persists and fear doesn’t drive sales).
War with Iran.
And even the surreal frustration of a TSA system that seems to forget how airports are supposed to work.
These aren’t just operational challenges. They’re energetic headwinds—the kind that seep into your team, your customers, your psyche.
They’re torturous.
And yet…this is the job.
Which is why, more than ever, you better love what you do.
Not in a romantic, Instagrammable way. But in a grounded, almost stubborn way. The kind of love that can withstand uncertainty, ambiguity, and the occasional desire to throw your laptop into the ocean.
You better be deeply committed to your mission.
Because when the external world becomes chaotic, mission becomes your internal compass. It’s what keeps you from overreacting to every headline or underreacting to real risks.
And just as importantly, you better help your people feel two things:
- The mission at work — what the company does in the world
- The mission in work — what they do inside the company
Because in times like these, people don’t just want a paycheck. They want to know their effort matters. That their contribution is part of something meaningful.
That’s the real insulation against chaos.
Entrepreneurship has never been easy. But today, it requires something more than grit.
It requires purpose with staying power.
Because when the winds are this strong, the only thing that keeps you standing…is knowing exactly why you’re still here.
If you’re an entrepreneur, I feel you. I know what you’re going through, the messy, dark, solitary chrysalis. Resilience will buy you time, but adaptability will buy you a future, so it may be time to adapt and evolve your business.
On Friday, I released a Midlife Chrysalis podcast episode with one of my favorite entrepreneurs in the world, Ari Weinzweig, the founder of Zingerman’s family of business in Ann Arbor, Michigan. If you’re looking for an entrepreneurial pitstop (and, Lord knows, you deserve one), consider joining me and Ari for our Santa Fe workshop, Radical Wisdom: The Natural Laws of Business and a Meaningful Life, May 24-28.
And, thanks so much for all of you telling your friends about MEA. In times like these, word-of-mouth support is incredibly valuable.
-Chip