on travel.
pack light, go big.
Growing up, we traveled a lot.
My dad worked for the airline industry — first, for American Airlines1, then for Sabre — so nearly every weekend, we’d pack our bags, head to Dallas-Fort Worth International airport, and hit the skies.
Looking back on it now, it was a pretty blessed childhood.
I had more stamps in my passport by the time I was ten than most people have in their entire lifetimes.
To be clear: we never traveled extravagantly.
I think my dad viewed “luxury travel” as a waste.
Why spend your hard-earned money on first-class seats, high-end hotels, and fancy restaurants, when you could simply… not?
Instead, we opted for coach, chain hotels, dives and street vendors.
There was little to complain about — we were traipsing around the world, after all.
Then, we went to Disney World in 2002.
That trip did something to me. Set me down a path toward stories, screens, the strange pull of media — but one small moment from it stuck for a different reason.
We were at Disney World. I was eight. Buzzed on sugar and possibility. Every time we passed a souvenir shop, I asked. Every time, my parents gently said: “Not now.”
I get it. Those shops were expensive, wasteful. Didn’t fit our travel philosophy.
Still, I watched other kids walk out with ears on their heads and characters in their arms. I tried to pretend it didn’t bother me.
When we got back to Dallas, my mom pulled a Mickey plush from her bag — something she’d picked up quietly, probably when I wasn’t looking.
It was thoughtful.
It meant something.
But it was a little too late.
And Mickey was… definitely not official.
Still, that moment stuck.
Not because of what I got — but what I almost didn’t.
It shaped how I travel now: chasing experiences, saying yes, dodging the kind of regret that only creeps in when it’s just a bit too late.
we travel well.
I can’t exactly pinpoint when my travel philosophy shifted. Maybe it was the consulting years. Maybe it was one too many bad hotel breakfasts.
But somewhere along the way, it became a well-known fact in our family: my sister-in-law and I have opinions about how we travel.
Let me put a finer point on it: we travel well.
And I’m not shy about it.
I points-max (a habit I picked up in consulting and never kicked), I pack and unpack with surgical precision (a gift, or maybe a curse), and I plan like the fate of the trip depends on it (it does).
I like a great hotel. An award-winning meal worth dressing up for. And a hole-in-the-wall joint that doesn’t show up on Google Maps until you’re standing in front of it.
So no, this isn’t a guide to budget backpacking or minimalist living.
This is for people who chase experiences like they matter — because they do.
Because if you’re like me, the quest for food isn’t just about making it, it’s about finding it.
The perfect bite. The perfect seat. The perfect street you weren’t supposed to turn down.
And that, my dear reader, requires, well, getting out there.
a million-miler who is perpetually on vacation.
The simplest way to describe my travel philosophy is this:
Plan like a million-miler. Indulge like you’re perpetually on vacation.
At first glance, those might sound like contradictions — but they’re not. In fact, the magic happens where they meet.
Let’s start with the million-miler.
You’ve seen them. The elite status holders. The loyalty-point whisperers. People who glide through security like it’s a form of art.
Their wardrobe is efficient: dark solids, wrinkle-resistant layers, elevated basics. A jacket that works for both business dinners and actual dinners. Sneakers that can survive a TSA sprint but still pass at a cocktail bar.
They never check a bag. Ever.
They roll through the terminal with an aluminum carry-on packed with militaristic precision: everything in cubes, everything intentional. A briefcase or backpack stacks perfectly on top. Nothing jingles. Nothing spills.
The million-miler is optimized — for movement, for uncertainty, for a life that’s always half in transit.
Then there’s the other archetype: the person who always seems to be on vacation.
You know the one. Their Instagram is all infinity pools, cobblestone alleyways, and #perfect-morning-light. They’re always at the dreamiest hotels, always at the best restaurants — and somehow their LinkedIn still says Senior Director of Equities at Haberdasheries, Inc.
They don’t travel light. They travel well.
So here’s the trick: don’t pick a side. Steal from both.
Bring one carry-on, but book the hotel you’ll still be daydreaming about a year from now.
Dress smart, but leave room for indulgence.
Be efficient — but don’t be stingy with your joy.
That’s the balance: minimize friction, maximize experience.
And above all, don’t come home wishing you’d done it differently.
Worst case scenario? Buy the swimming trunks from the hotel gift shop and have them shipped home.
my travel essentials.
If you’re going to travel like a million-miler and someone who’s perpetually on vacation, you need gear that does both: streamlined enough to fit in one carry-on, but thoughtful enough to elevate the whole experience.
So I’m not going to stand on ceremony here — just a quick list of what always comes with me, whether I’m flying across the country or across the ocean.
iPad + headphones — In-flight entertainment is hit or miss, so I bring my own: an iPad loaded with movies and shows, and noise-canceling headphones that block out everything but the good stuff.
A jacket2 — Straight from the million-miler playbook. Keeps you warm on the plane, dresses you up for any occasion, and (pro tip) dramatically increases your upgrade odds. Denim, bomber, or blazer? Choose your fighter.
(White) sneakers3 — Versatile, comfortable, and polished enough to work for everything from airport sprints to rooftop dinners. My go-to move.
Hat4 + sunglasses5 — A power combo. Great for hiding plane hair, under-eye bags, or a general lack of sleep. Also useful for pretending you’re not from here; wherever here is.
Mini toiletry kit — A hack I stole from some YouTube everyday carry guru (“EDC” for us nerds). Take the essentials from your main kit (face wipes, meds, Aquaphor, etc.), decant them into travel-sized containers, and stash them in a tech pouch (I use the Orbitkey 2-in-1). Total game-changer on long-haul flights.
There are more — my watch, my camera, chargers, water bottle, eyeglasses, laptop, and of course the bags themselves — but we can save those for another time.
en place.
I was going to end this with more lists — my favorite hotels, restaurants, cities.
The places I’d go back to in a heartbeat.
But then I thought: you don’t need my lists (though I’m happy to share if y’all are interested).
Because whether you’re interested in heading to Italy or India or somewhere in between, the truth is: the place isn’t the point — not really.
It’s how you feel there.
Who you become while you’re there. What you almost missed — but didn’t.
Travel’s not about checking boxes. It’s about what lingers.
The meal you can’t stop thinking about.
The alley you wandered down by accident.
The moment you said yes instead of not now.
I think about that a lot — how close we are, always, to missing something we didn’t even know we needed.
So bring the carry-on. Book the hotel. Order the dessert. Buy the overpriced hotel merchandise.
Travel like a million-miler who is perpetually on vacation.
Get out there. And above all — don’t come home wishing you’d bought the Mickey Mouse plush sooner. Just get the damn thing.
To my friends and family: this should explain my life-long penchant for flying OneWorld airlines, even if it’s an inconvenience. Looking at you, Jamie.
My current go-to: the Storm System packable jacket from Loro Piana. It’s a dream.
My current go-to’s are the Maison Margiela Replica sneakers.
My current go-to hat: the Loro Piana cashmere hat OR a hotel hat.
My favorite sunglasses are the Oliver Peoples O’Malley Sun, but have also been wearing the Jacques Marie Mage Zepherin a lot lately.