Next week, I’m boarding a plane to Valencia, Spain with my wife and two small kids. We’ll be in Valencia for a month, then spend a week in Maine with my wife’s family. This is our first international trip since becoming parents, and it’s a significant departure from the day-to-day rhythm that governs my life—one that usually plays out within a three-mile radius of our house in Carrboro.
When I tell people what we’re doing, I usually get the same reaction:“You’re doing what?”
Understandably so. Taking two toddlers abroad for a month sounds ambitious (or chaotic, depending on who you ask). Add in the fact that I’m the CEO of a growing healthcare company, and it gets even more improbable. But that’s part of the reason I’m doing it.
People are surprised for three main reasons:
- I’ve historically been a workaholic.
- Traveling internationally with two kids under four is… bold.
- There’s a deeply held belief that CEOs need to be physically local to lead effectively.
Why We’re Going
My wife and I both love to travel, but we’ve largely paused that part of our lives since having kids. Life turns into logistics—packing lunches, drop-offs, playdates, dishes. We’ve missed the sense of wonder that comes from being in a new place, the way it slows you down just enough to notice the small things and enjoy the everyday moments.
We fed our criteria into ChatGPT (exchange rate, safety, healthcare access, walkability, public transportation, climate, outdoor space) and came out with a few options: Porto, Barcelona, some Croatian city, and Valencia. We landed on Valencia. It’s family-friendly, highly walkable, has great food, and plenty of kid-friendly activities. We found an apartment in a great neighborhood—walking distance to Ashtanga Yoga House—and started planning.
While my wife has taken the lead on family logistics—playgrounds, day trips, nap schedules—I’ve been preoccupied with a different question:
What does it mean to lead a company when I’m physically absent?
The Guilt of Going
There’s a part of me that feels like I don’t deserve this. I’ve carried stories about what leadership “should” look like, and one of those stories is that you don’t leave. Not for long. Not while others are holding down the fort. Not while there’s work to be done (read: always).
But I’ve also started to realize something I should’ve internalized long ago: Being “always on” doesn’t make me a better leader.
In fact, it can do the opposite. When I’m too close to the action, I unintentionally get in the way. I insert myself into problems my team is already equipped to solve. I carry tension that isn’t mine to carry. I default to doing instead of leading.
This trip is a kind of permission slip—to trust the team, to operate at a different altitude, and to reorient myself toward longer-term, strategic thinking.
A Leadership Reset
For the past few years, I’ve been deep in the weeds: launching new services, building our data infrastructure, negotiating insurance contracts, recruiting A players. All of it was necessary. But it’s also been all-consuming.
I’m overdue for a reset. I need to step back and spend more time thinking about:
- Vision
- Brand
- Culture
- Structure (that scales)
- Strategic positioning
This isn’t a typical vacation—I’ll be working EST hours most days. My tentative schedule looks something like this:
- 6:00–7:00 a.m.: Meditation, reading, journaling
- 7:00–9:00 a.m.: Ashtanga yoga at a local studio
- 9:00 a.m.–3:00 p.m.: Family time (parks, museums, beaches—just being present)
- 3:00–11:00 p.m.: Work
This rhythm lets me show up for my team and our company, while also being present with my family during the best part of the day. It feels like a win-win—but it’s also a test:
Can I lead from across the ocean without slipping into over-functioning?
Letting Go (Finally)
One of the more humbling parts of building a company is realizing that you’re no longer the best person to do most things. That’s where I am now.
Our executive team is stronger than it’s ever been—and far more capable than I am in their respective domains. That may have been true for a while, but this is the first time I’ve fully felt it. And trusted it.
This trip is both a test and a signal: a test of our systems + a signal of my trust.
On a Personal Note
None of this would be possible without my wife. She’s carried more than her share of late nights, tight budgets, emotional whiplash, and general uncertainty.
When we started dating, I was in law school and she was in a PhD program. We (she) had a vision of stability and high salaries. Then I dropped out. I started a healthcare company. We had two kids. We went through some lean years. And I’ve worked like hell to get us to solid ground—but she’s carried a lot along the way.
This trip is a way to finally access some of the upside of entrepreneurship: flexibility. Freedom. Time.
I want to give my family a version of me that isn’t always rushing, distracted, or preoccupied with the next fire to put out. I want to walk slowly. I want to be the one who slices the fruit, who runs through fountains, who reads too many bedtime books (though let’s be honest—current conditioning makes that unlikely).
If entrepreneurship doesn’t buy moments like that, then what’s the point?
What I Hope to Learn (or Unlearn)
This trip wasn’t inspired by wanderlust or Instagram daydreams. It was shaped by reading Four Thousand Weeks and realizing how deeply out of alignment I’ve been with the life I actually want to live.
This is an experiment in alignment. In slowing down. In trusting.
Some of the questions I’ll be sitting with:
- What parts of my leadership are rooted in control, not trust?
- What rhythms help me flourish—personally and professionally?
- What am I still holding on to that I don’t need anymore?
- Can a founder step back without stepping away?
- What kind of father, husband, and CEO do I want to be ten years from now?
I expect a few things to happen:
- The team will function better than ever—which will be both humbling and liberating.
- I’ll begin to redefine the relationship between work, family, and rest—and find a more sustainable rhythm for the long haul.
Final Thoughts:
We live in a culture that glorifies urgency, speed, and constant availability. But the real work—at least for me—is knowing when to slow down, and why.
This trip is a recalibration. A chance to work differently, live more fully, and lead with clearer intention.
And hopefully, it’s the first of many experiments in building a life that’s aligned—not just efficient.