A Life Measured in Trips
There's a version of my life where I'm perpetually somewhere else — a different city every month, no fixed address, a passport with no blank pages. I've made my peace with the fact that version isn't mine. The job, the mortgage, the calendar full of things that need doing: they're all real, and I'm not pretending otherwise. What I have instead is something I've come to value more than the fantasy — the kind of traveler who treats every trip as precious precisely because they're not infinite.
Since my daughter arrived in 2023, that feeling has sharpened into something almost urgent. There is a specific joy in watching a small person encounter the world for the first time — the ocean, a mountain, a city that smells and sounds like nothing she's ever known. I want her to grow up understanding that the world is large and strange and worth exploring. The best way I know to teach that is to show her.
So we go. Not as often as I'd like. But when we do, it counts.
The Obsessive Planner
A great trip doesn't happen by accident. It's designed. I've spent years treating itinerary planning less like a chore and more like a craft — the kind where you fall down a rabbit hole of satellite maps, obscure travel forums, and elevation charts at 11pm on a Tuesday. My north star is pacing: that precise sweet spot where the trip feels full without feeling rushed, where there's enough white space to be surprised. I dig for the spots that don't make the listicles, cross-reference opening hours across time zones, and map driving routes around the light rather than the clock.
My current tool of choice is Blue Planit's Travel Mapper — clean interface, Google Sheets backbone, exactly the kind of thing a spreadsheet person with aesthetic sensibilities would build if they got tired of ugly planning tools.
The Road Less Indexed
My compass points away from the crowds, almost reflexively. Not out of contrarianism — I genuinely believe the best version of most places is hiding just past where the tour buses stop. The true Hawaii, for me, isn't Waikiki. It's a trail on Kauai where the only sounds are wind and your own breathing. I'm drawn to dramatic landscapes, small towns with outsized stories, and destinations where nature hasn't yet been edited for mass consumption.
How You Move Is Part of the Trip
The way you get somewhere is a design decision, not just a practical one. In the American West, nothing unlocks the landscape like a car — the ability to pull over mid-nowhere because the light just turned extraordinary is a freedom I'll never take for granted. But I'm equally in love with the counterpoint: traversing China at 300 km/h on high-speed rail, taking a slow ferry across a harbor with no particular agenda, boarding a local bus just to see where it goes. Transit, done right, is itself a cultural experience. Some of my best travel memories are just sitting and watching the world go by.
Luxury Is a Skill
Premium travel doesn't require a premium budget. With the right credit card strategy — points, miles, transfer partners — I've consistently flown business class and stayed in hotels I'd otherwise only photograph from the outside. It takes some homework upfront. It's absolutely worth it.
Credit cards are just one piece of a broader financial philosophy I've spent years developing — if you want the full picture, I have a dedicated page on how I think about money, investing, and building toward the life I actually want.