I’d booked myself afternoon tea in Osaka, which is one of my favourite things to do when I travel, and on this particular day I was running late. I’d been working and was taking a break in the middle of the day to go, so I walked there a bit harried, with the feeling that the clock was ticking. A train would have been faster, and a taxi faster still. But I wanted to walk, because the walk was part of my break from work.
When I finally sat down, the harried feeling just drained out of me. They’d seated me where I could look out onto a little garden, the service was the kind where you feel they’re genuinely happy you’re there, and I love those small careful touches. The sun was moving across the room, and once it reached the tables, a waiter came over and lowered the blinds just enough to shade mine. The food kept coming: soup and a salad and seafood, more than I could eat. I didn’t try to finish it, but I enjoyed every minute of what I ate. And mostly I sat there and watched how everything moved through the space.
Nothing about that afternoon would make a list. There was no famous building, nothing I could point to and say you have to see this. It was a walk I chose, a table by a garden, soup and seafood and sun, and it was one of the best afternoons of the whole trip. Days like this remind me that there isn’t one right trip to find. Planning a trip you’ll actually enjoy is less about logistics than it is about design.
In this episode:
- The myth of the one right trip
- The subtraction effect
- Being good company for yourself
- One swap before you go
“Planning a trip is about design, not logistics. You design it for the woman who is actually going.” (Damianne)
Why is there no one right trip to plan?
There isn’t a perfect itinerary sitting out there that you’ll finally find if you research hard enough. What’s right depends on the season you’re in, and on the moment. The right trip for me a few years ago isn’t the right trip for me now, and the right afternoon on day one of a trip isn’t necessarily the right afternoon on day four. So for me, right is much more about tuning into the moment and recognizing how it’s going, and about feeling my feelings rather than being afraid of them or avoiding them.
Some days, right is afternoon tea in London, or Cape Town, or Osaka. And some days right is realizing there’s an invitation in front of you, some new friends, a plan already in motion, and the right thing is to say yes to that instead. Once I see it this way, the whole question of planning changes. If the trip is time with myself, then the test of a good plan is whether I wanted to be there.
This is one reason I think the 40+ solo travel advantage is real. By this point, you know more about your actual self than you used to. You can let that knowledge shape the trip.
What does it mean to be good company for yourself?
Intentional solo travel is really about being with yourself. It’s the same as when you take a trip with a good friend because you want to spend time with her and get to know her better. You’re doing that with yourself, and the whole trip is the company you’re keeping with you.
So I look for chances to laugh with myself, or sometimes at myself, and to find the amusement in things. If it’s something I’d laugh at with a friend, why can’t I laugh at it even when I’m by myself? I try to catch the moments where I’d normally hold back from enjoying something out loud just because there’s no one next to me, and I let myself enjoy it anyway.
I later learned there’s a name for the deeper version of this. Psychologists call a choice that genuinely fits your own values and interests self-concordant, and they’ve found that when something fits you like that, you put more of yourself into it and get more back out of it. That’s the whole difference between an afternoon you chose and an afternoon you endured.
How do you actually design a trip around yourself?
You subtract. Most planning goes wrong in the first ten minutes, when you open the search and within a few minutes you have a long list of the things you’re supposed to do in this place, the famous landmarks, the walking tour everyone rates, the day trip you’d feel silly skipping. None of it came from you. So before you add a single thing, look at what’s on the plan and ask, honestly, which of these is here because I want it and which is here because I think I should, and then take the shoulds off.
I find this harder than it sounds, and there’s a reason for that. Researchers have found that when people try to improve something, almost anything, they reach for what they can add and overlook what they could take away, even when removing it would make the whole thing better. We’re wired to add, so subtraction takes a little courage and a little practice.
I was in Krakow recently for work with one free evening, and the should showed up right away: download a guide, go exploring, make the most of a beautiful city. But I’d had a busy week, and what I actually wanted was a face mask, a couple of episodes of a Korean drama, a book, and bed. I walked around for about an hour and that was it, and it was exactly right for that evening. The proper exploring would have been me performing a trip I didn’t have the energy for.
If you’re planning something bigger, the adult gap year episode is a good companion: Your Adult Gap Year Doesn’t Have to Be a Year.
But won’t I be bored or lonely on my own?
This is the worry I hear most, the sense that a trip is just better with other people and a solo trip is the lesser version. I’m not going to tell you a trip alone is the same as a trip with people you love. It’s different, but different isn’t worse, and neither one is necessarily better. When you travel with someone you split your attention, which is lovely. When you travel with yourself, all of that attention comes back to you.
And being on your own doesn’t mean being alone the whole time. Years ago in New Orleans I went to Preservation Hall by myself and it was incredible, and I didn’t need anyone next to me for it. On the same trip I met people through the Couchsurfing app, and they were heading to a late show by the Rebirth Brass Band, who I knew nothing about and who turned out to be Grammy winners. I’m not a night owl and I almost didn’t go, but I wanted to spend time with these people who seemed kind, so I got dressed and went out with a group from all over. New friends are one of the best parts of travelling alone, and all it takes is a little curiosity when you meet people. The loneliness you’re picturing usually assumes you have to be solo the whole time, and you don’t.
The decision underneath all of this is often smaller than we expect. I wrote more about that in The Decisions That Build a Solo Traveler Aren’t the Big Ones.
Your invitation for this week
Look at your next planned trip, or the one you’ve been turning over in your head, and find one thing that’s there because you think you should. Maybe it’s the famous landmark you don’t actually want to queue for, the walking tour you already know you wouldn’t enjoy, or the early start that asks you to be a kind of morning person you aren’t. Take it off. Then put one thing in its place that you actually want, even if it sounds boring on paper, like an afternoon with nothing in it, a long lunch by a window, or a bus you’ll ride and not get off. And just notice how you feel about the trip after that one swap.
Taking one thing off matters more than adding ten good ideas, because adding is the easy thing we do on autopilot. Subtracting is the harder move, and it’s the one that makes the trip yours. When you make the swap, notice what happens in you. I’m hoping for a little tenderness, and a little curiosity, because designing a trip around the real you is a way of getting curious about who she is, the young woman you were with all her dreams and the woman you’ve become who has learned so much along the way. In solo travel we get a chance to meet all of ourselves.
Join community
If you want to do this with a whole trip and not just one swap, come into the community. That’s where we keep practicing how to design around the woman who is actually going, not the woman we think we’re supposed to be.
The community on Skool is a supportive space where you can build momentum, get clarity and start choosing yourself again.