A lot of us have a list somewhere, whether in a notes app, in a folder, or just in the back of our heads. It’s a list of all the places that look interesting, where we might go someday. And although every place on it sounds lovely, not one of them is an obvious yes. So we keep researching, and we keep not choosing. I’ve watched so many women do this, and I’ve done it myself. We treat the indecision as a sign that we haven’t found enough information yet when really it’s a sign that we’ve been asking the wrong question from the start.
I don’t think the problem is that you don’t know what you want. If you’re a woman over 40, you usually know what you want by now, at least in principle. The problem is that you’ve gotten so good at choosing what’s sensible, or what other people would approve of, that the muscle for choosing what you actually want has gone quiet, too soft to hear. So you look at that list one more time, and you can tell which places are the right ones, but you can’t commit to the one you actually want.
This episode is about the question that gets you off the list and into the trip.
In this episode:
- The 15 best places trap
- Situation selection, explained
- Following the feeling, not the feed
- Beauty at Kuang Si, ease in Japan
- Aliveness in Hanoi, warmth in Albania
- Your one feeling, your one place
“The best destination for you is not the safest one or the most popular one. It is the one that matches the feeling that you want to have on the trip.” (Damianne)
Why does more research make it harder to choose?
We sort by which place is safest, which place is most impressive, and which place we see most on social media with the most things to do. These are all fine things to think about. They’re just not the first thing, and they’re not the thing that actually gets you on the plane. So you start there, and you end up with a list of good answers, and you still don’t go.
And the more you read, the longer the list gets, and the longer the list gets, the harder it is to choose. Then you tell yourself you’ll figure it out later, when you have more time to really look into it. If this is the loop you’re in, you might recognise yourself in the destination indecision episode too, and in the companion episode on how to actually choose a destination. What I’ve come to believe is that the best destination for you isn’t the safest one or the most popular one. It’s the one that matches the feeling you’re craving right now. You pick the feeling first, and then you pick the place, not the other way around.
What if you’re sorting by the wrong thing?
There are two ideas from psychology that completely changed how I think about deciding a destination. The first is situation selection. Of all the ways you can change how you feel, the one that does the most work is choosing which situations you put yourself in. You already do this without thinking. You put on a certain kind of music, or a certain show, when you want to feel something specific. A trip is just a very big, very deliberate situation that you get to choose on purpose.
The second is affective forecasting, which is a slightly clinical way of saying we’re surprisingly bad at predicting what will actually make us feel good. The researchers who named it, Daniel Gilbert and Timothy Wilson, found that we lock onto one obvious feature of a future experience and let it crowd out everything else. So we look at a place and fixate on the loud thing. Is it safe? Is it impressive? Will it photograph well? And then a bucket-list trip can leave us feeling almost nothing, while somewhere unglamorous undoes us in the best way.
Social media makes this worse because now the loud feature isn’t just in our heads; it’s right there in the feed. We see the one perfect photo, the most photogenic corner of a place, and we forecast the whole trip from it. We’re not even predicting our own feelings anymore. We’re borrowing somebody else’s highlight. Choosing the feeling you want is how you climb back out, because the feeling is yours in what’s really yours.
What does it look like to choose for a feeling?
Here are four of the feelings I’ve chosen trips for, with a place attached to each. The feeling I come back to most is awe, and the place I think of is Kuang Si in Laos, those pools one above the other, water so clear and blue I stood there wondering if it could possibly be natural. Everywhere I looked was beautiful. There are pools to swim in, but for me the whole experience was about seeing, not getting in.
Then there’s ease, which sounds small until your real life is taking everything you’ve got. I spent a month in Japan recently, and a simple local bus to Nachikatsuura, in a language I don’t speak, with everything clearly signed, left me feeling completely taken care of.
There’s aliveness, the opposite of numb, which for me was Hanoi, where you have to be switched on just to cross the street.
And there’s warmth, human warmth, which I found at a table in Albania where someone left a full spread of food to go and buy bread because a guest should be properly looked after.
The point isn’t these four places. It’s that each one matched a feeling, and the feeling is what made it right. This is the same clarity I talked about in the 40+ solo travel advantage: by now you know more than you used to about what actually delights you.
How does the feeling arrive for you?
This part matters more than it sounds. For me, awe usually comes through my eyes. I’ve stood at a lot of waterfalls where people asked, “Aren’t you going in?” as if I wasn’t really there unless I got wet. I don’t have to get in the water to be moved by it. Knowing how a feeling reaches you, through your eyes, your skin, your stomach, or a conversation, is its own kind of self-knowledge, and it changes what you should choose. So if you’re hungry for beauty, you need scenery that doesn’t let up,and it doesn’t have to be expensive. If you’re hungry for warmth, you go where people pull up a chair.
A small invitation
Here’s your invitation for this week. Name the one feeling you want most from your next trip. Maybe it’s one of mine: ease, beauty, aliveness, warmth. Or it’s something completely different. Then match it to a single place you believe would give you that feeling. And if you want to take it one step further, open your calendar and block a three-day window to research only that one place. You’re not booking anything yet. You’re just letting the feeling pick a place, and giving it a little room.
Take the Solo Trip Fit quiz
If you’re not sure what feeling to build your next trip around, that’s exactly what my Solo Trip Fit quiz is for. It’s a quick way to see what stands out for you right now and which feeling might be the right one for your next solo trip.
Take the Solo Trip Fit quiz: https://freedomlookslikethis.com/solo-trip-fit/