The Letter

What Twenty-Five Years Abroad Taught Me About Traveling Alone

I moved to the UK in 2001 with one of the Big Four accounting firms, a job title I could barely pronounce with confidence, and the kind of certainty you only have before you have actually done the thing. I grew up in upstate New York. I started my career in New York City, which I thought had prepared me for anywhere. It had not. Nowhere prepares you for anywhere. That, it turns out, is the whole lesson, and it took me twenty-five years to get it down to one sentence.

Here it is: foreign is a feeling, and it fades with competence, not with time.

When I first heard a version of that — much later, from someone wiser than me at a dinner party I was too jet-lagged to enjoy properly — I thought it was a nice turn of phrase and nothing more. It is not a turn of phrase. It is the actual mechanism. You do not stop feeling foreign in a place because you have clocked up years there. You stop feeling foreign the moment you can do the ordinary things without translating them in your head first.

The supermarket, not the skyline

My first supermarket trip in England was harder than any city break I have taken since — and I have now traveled to more than seventy cities in this catalogue alone, most of them solo. That first trip, I stood in front of a wall of items I half-recognised, converting prices in my head, and I did not know if "biscuits" meant what I thought it meant, or something closer to what I would call a cookie, or something else entirely.

I did not know which queue was actually a queue. I did not know that "you alright?" from the cashier was not a health check — it was just hello, and answering it with an actual update on my wellbeing marked me out as new in ways my accent already had. I carried two currencies in my purse for months, doing the maths twice on everything, unsure which pocket held which country.

None of that was about England being far away. It was about competence — the thousand small fluencies you do not know you have until you are standing somewhere they do not apply:

Once you have rebuilt that stock of small competences in one new place, you find out something useful. The rebuilding gets faster every time — not because the place is familiar, but because you have gotten good at not knowing. You know what to look for. You know that the first grocery run, the first ticket machine, the first "how do I ask for this" is the whole test, and that it passes in days, not years.

Why I would rather book the trip than "settle in"

That is why I would rather take a solo city break somewhere I have never set foot than settle in somewhere for a month before I feel entitled to explore it. The tenth city break is nearly always easier than the first supermarket trip anywhere new, because by the tenth trip you have stopped needing the place to feel familiar. You have just gotten quick at figuring out the parts that are not.

I think this is the piece nobody tells women traveling alone later in life, and it is the reason I wanted this column to exist. We are braced for the big, dramatic unknowns — the language, the safety, the logistics of getting from A to B without anyone else's name on the booking. But the thing that actually wears you down in the first forty-eight hours anywhere new is never dramatic. It is granular:

And the good news — the thing twenty-five years has proven to me over and over — is that granular things are exactly the things you get fast at solving. Competence transfers. Confidence, oddly, does not have to. You can feel a little unsteady and still be entirely capable, and after enough trips you learn to trust the capability over the feeling.

What I would tell you, standing in that aisle

So here is what I would say to anyone standing in an unfamiliar supermarket right now, purse heavy with the wrong currency, unsure which queue is real. You are not behind. You are exactly as far along as everyone else was on their first day, including me on mine. It gets easier by Thursday. It always does.

What is the "foreign supermarket moment" from your own travels — the small, unglamorous thing that told you you had landed somewhere new before anything else did? I would genuinely love to hear it.

— Jennifer

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