A client called last month. Smart guy, head of engineering at a 90-person startup, makes good money, has been a client for three years. He opened with: “Shane, I want to do twelve countries this year. I’m going to call it my Year of Adventure.”
I told him no.
Not “let me try” or “interesting, let’s see what we can do.” Just no. Then I told him what we’d do instead, which was three trips — two weeks each, deep into one place — and I’d rather lose his business than help him execute his original plan. He hired me anyway. He’s about to come back from his second of three trips. The first one was the best two weeks of his year and he’s already talking about going back to the same place next time.
This is the conversation I keep having. People come in with bucket lists — long ones — and the bucket list is the problem.
How the Industry Got You Here
The travel industry sold you the bucket list because it sells more trips. A 50-item list of places-before-you-die is an annuity. You’ll come back next year, and the year after, with a new line item. The cruise lines, the airlines, the booking platforms, the influencer travel content — all of them benefit from you treating travel like a checklist to grind through.
The thing is, that’s not how anyone who actually travels well does it.
The most experienced travelers I know — the diplomats, the foreign correspondents, the cruise line executives, the people who’ve been everywhere on someone else’s expense account — almost universally have short favorites lists. They go back to the same fjord in Norway every other year. They book the same lodge in Botswana three years running. They have a small village in Tuscany where the proprietor knows their order. They’re not collecting countries. They’re cultivating relationships with places.
What “Going Deep” Actually Looks Like
Here’s the test. Pick a country you’ve been to once. Now answer these without Googling:
- What did the air smell like in the morning?
- What was the worst meal you had there, and why was it bad?
- Who was the person you remember most from the trip — not the friend you went with, but a stranger?
- If you went back tomorrow, what’s one specific place you’d want to revisit?
- What did you misunderstand the first time?
If you can answer four of those five, you went deep. If you can answer one or two, you visited.
I’ve sent people to Antarctica, the Galápagos, Iceland, Japan, Norway, Patagonia, Botswana, all the heavy hitters. The trips that change them aren’t the ones that hit four places in seven days. They’re the ones where they spent eight nights in one camp, or fourteen days on one ship, or a month in one country with a great car and a flexible itinerary.
The Math Is Counterintuitive
Twelve countries in one year sounds like more travel than three trips. It isn’t.
Twelve countries means twelve airport mornings. Twelve hotel-check-in dances. Twelve “what’s the WiFi password” interactions. Twelve flights with the seat-back screen frozen on the safety video. Twelve days of recovering from jet lag instead of using them. By trip four, you can’t remember what was particularly different about trip two. You’ve spent the year accumulating boarding passes, not memories.
Three trips of two weeks each means about 42 travel days. The first three days of any trip are setup — finding the rhythm, recovering, getting your bearings. Days four through ten are the trip itself. Days eleven through fourteen, you actually start to belong. The day-fourteen version of you in Tuscany is unrecognizable from the day-three version. That growth doesn’t happen on a four-day stop. It happens when you’ve stayed long enough that the same waiter at the same trattoria starts making suggestions you haven’t asked for.
The Three Categories Worth Taking Seriously
If you ditch the bucket list, what replaces it? In my experience, three kinds of trip actually move the needle:
The Anchor Trip. A place you go back to, year after year, that becomes part of who you are. For some clients it’s a particular Caribbean island. For others, it’s a specific lodge in Africa or a town in Italy. The accumulated experience of seven years in the same place beats seven different countries every time. The people there know you. You know which boat to take, which restaurant has the table by the window, which guide actually likes their job. You arrive already in the trip.
The Threshold Trip. A trip designed to mark a real transition — a milestone birthday, an empty nest, a sabbatical, a recovery from something hard. These trips deserve their own intentionality. You’re not collecting countries; you’re processing a life change. The places that work for threshold trips tend to be quiet, slow, and somewhere with weight to it: Bhutan, Iceland, Japan, the Alaskan inside passage, a Norwegian fjord. These trips are often best at 14-21 days.
The Real Adventure. Once a decade — or once a life — there’s a trip that’s actually new and hard. Antarctica. The Northwest Passage. A serious safari into the Okavango Delta. A multi-week expedition in Patagonia that requires actual fitness. These trips earn their place on a list because they’re transformative, not because they’re famous. You don’t take three of them in a year. You take one, and you remember it for the rest of your life.
That’s three kinds of trip. None of them are “knock out four cities in Europe.” If your travel year fits into these three categories, you’ll get more out of one trip than the bucket-list person gets out of four.
What I Tell Clients Who Don’t Want to Hear It
Some clients won’t listen to this. They want their year of adventure, their twelve-country sprint, their checked-off list. I can deliver that. The systems exist; the prices are knowable; the bookings are mechanical.
But here’s what I tell them as we’re booking it: the version of you who comes back from twelve countries is going to envy the version of you who took three trips and went deep. And six years from now, when you’re trying to remember which of those twelve countries had the bridge with the lights and the bridge with the bagpipers, you’re going to wish you’d done it differently.
The clients who are easiest to work with are the ones who already know this. They come in saying things like: “I want to spend three weeks somewhere I’ve never been, somewhere quiet, somewhere with great food, somewhere I might want to come back to.” That’s not a bucket list. That’s a person who’s done some living and figured out what travel is actually for.
The Honest Pitch
If you want a list of fifty places before you die, there are a thousand websites for that. Don’t hire me. Don’t hire any travel advisor — you’re spending money on a service you don’t need.
If you want help figuring out what your anchor place is, or how to plan a threshold trip that actually works, or which of your three or four serious adventures should be next — that’s worth a conversation.
The most valuable thing a travel advisor can do isn’t book your trips faster. It’s help you trade ten okay trips for two great ones, and watch what happens to you over the next ten years when you stop chasing countries and start belonging to places.
Reach out when you’re ready to think about it that way.
