Bay to Barca
I’ve spent 20 years telling clients to “do hard things.”
Here’s proof I take my own advice:
You know that voice that says, “Well, what if we just…left?” I listened to it.
We moved to Barcelona.
Look, I'm 47 with three kids. Sara and I had everything figured out in the Bay Area.
But here's what kept bothering me:
I found myself having the same conversations over and over.
Football, real estate, stock picks. I'd go to these dinners and think, “How many times can we talk about the same stuff?”
We get really good at executing the playbook, but sometimes you need to throw out the playbook entirely.
Sometimes you need to do hard things. You have to be comfortable being uncomfortable.
So, we packed up our family of five and moved to Barcelona. Now Sara and I are writing about it.
And I'm still running Object Edge full throttle. Turns out you can do hard things from anywhere.
But being here, watching my kids navigate new playgrounds in a new language, sharing killer views with Sara on Sunday afternoons…it's irreplaceable.
If you're curious about what happens when a tech CEO trades Silicon Valley for the Mediterranean Sea, when a family chooses adventure over optimization, come along for the ride
Bay to Barca
Episode 7: Honeymoon's over, but we are still in love
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Soccer wins, Sunday blues, and the seven changes we’re making to fall back in love with life abroad.
We’ve officially entered the “trough of disillusionment.”
That magical phrase every expat hears about but hopes won’t apply to them. Turns out—it does.
This week, we’re talking about what happens after the honeymoon. When the novelty fades, the logistics pile up, and the question “how long are we staying?” starts sounding less hypothetical.
But first, big news:
After weeks of checking Spain’s football federation site hourly, Sara finally saw the word “Approved.”
Amalia can now officially play for her Barcelona team. There were tears (Sara’s), relief (mine), and a collective lifting of the dark cloud that had hovered over our weekends.
With that, we started asking ourselves—what else can we do to make life here better?
I actually made a list. Seven things, to be exact:
- Amalia’s soccer approval. Check. ✅
- Hire a driver. Because spending four hours in traffic to soccer practice isn’t romantic.
- Reclaim our terrace. We’re adding a netted play area so the kids can actually use it.
- Get organized. Enter the Skylight Calendar, our new family command center.
- Find a finca. Somewhere an hour outside the city, for weekend escapes.
- Maybe (maybe) get a dog. Jury’s still out.
- Travel more. Because part of moving abroad is remembering to explore it.
We also get into some real talk:
- How living in a big city changes the way you experience time.
- Sara’s Sunday struggles (everything’s closed—and she’s not over it).
- The not-so-warm warmth of Catalonian service culture.
- And why no one here cuts their pizza slices for you. (Still a mystery.)
There’s also some joy sprinkled in—paddle matches with new friends, morning rides on my new Brompton bike, discovering an incredible Ecuadorian hole-in-the-wall (El Nano), and the best Indian food we’ve found in Barcelona (Shanti—highly recommend).
Somewhere in between, home started meaning two places at once.
San Francisco felt like home when I visited. But so does Barcelona. And maybe that’s the point—home isn’t one address anymore, it’s a balance between them.
We’re learning that expat life isn’t an escape. It’s just a different kind of living—with its own rhythms, challenges, and tiny joys.
🎧 Listen to Episode 7 of Bay to Barca:
“The Honeymoon’s Over” — now streaming on Spotify and Apple Podcasts.