The Rooftop, the Wine, and the Woman Who Changed Everything

People ask me all the time how I ended up here — running a curated travel company, designing journeys for people who want to go deeper into the world rather than just through it. And the honest answer is: a party in Cairo. Wine and cheese. And a woman I'd never met before who had a very nice apartment.

But I'm getting ahead of myself.

Before the Foreign Service, before the diplomatic postings and the UN corridors and all of it, there was a version of me living on a rooftop in Cairo. Not on a rooftop — technically I had four walls and a door — but my apartment was built on top of the building, accessible only by stairwell, baking in the Egyptian heat while everyone sensible below me had something resembling air conditioning. I was so broke I couldn't afford the basement unit, which would have been cool and quiet and mercifully underground. Instead, I had the sky.

I was there for what was supposed to be a semester abroad. I stayed four or five years.

Cairo does that to people. There is no city on earth quite like it — not in energy, not in scale, not in its absolute refusal to sleep. You could be out at three in the morning and twelve million other people would be out there with you, completely unbothered, as if the whole city had quietly decided that night was just another kind of day. I studied Arabic. I ate things I couldn't name. I horseback rode at the pyramids in the dark. I fell in love with a city in the way you can only fall in love with a place when you are young and broke and have nothing to lose and nowhere else to be.

I learned my Arabic in classrooms and then, more fluently, in the back of taxis. It was street Arabic — gutter Arabic, my Egyptian friends called it, affectionately and not. Colloquial, immediate, exactly wrong in all the right ways. I can still navigate a city with it. I can still make myself understood. And I can still, as I will readily admit, deploy every swear word with considerable precision.

It was during those years that I stumbled into history without quite knowing it.

A friend — a journalist, I think, or someone adjacent to that world — suggested we cross into Israel, and from there into the West Bank. I said yes the way you say yes to things when you're twenty-two: without fully understanding what you're agreeing to, propelled mostly by curiosity and the mild recklessness of someone who has not yet learned to be cautious.

We arrived on the day of the first Palestinian elections. Yasser Arafat had long been the de facto leader of the PLO, but this was different — actual elections, actual ballots, a moment that history was quietly circling. There were journalists everywhere. There were election posters on every wall. And there was me, standing in front of one of those posters, a young woman from the United States who had no idea she was standing inside a page of history.

I did not know. That's the honest truth of it. You're twenty-two, someone offers you a ride to Bethlehem, and you go. You don't know you're in the middle of something. You're just there — present, wide-eyed, completely unqualified, and somehow exactly where you need to be.

I think about that day often now. I think about how different the world looks today compared to that moment. And I think about how travel, at its most honest, is exactly this: arriving somewhere without a script, without a brief, without knowing what you'll find — and letting it change the shape of you anyway.

The wine and cheese party came later.

I was invited to a gathering at an apartment in Zamalek — one of Cairo's loveliest neighborhoods, the kind with high ceilings and balconies and a view of the Nile. The woman who lived there had set out actual wine and actual cheese, which, when you are living on a rooftop with a tenuous relationship to your own address, is the height of civilization.

I asked her what she did for a living.

I'm a diplomat, she said. I work for — and she named her country.

I stared at her.

That's a job?

I mean this literally. I did not know. I had been living in the Middle East for years and had developed, by any measure, a genuine and serious interest in the world. But the idea that someone would pay you to live overseas — would provide the apartment, the title, the institutional weight — had simply not assembled itself into a coherent reality in my mind until that moment. I had a master's in international relations. I spoke Arabic.

She had a car. She had a salary. She had cheese.

I went home to my rooftop and started thinking about the Foreign Service.

That is my origin story. Not glamorous, exactly. Not the version where a young idealist is called to public service by some great and noble impulse — though of course I cared about the world, of course I did. But the moment that actually moved me to act was standing in someone else's beautiful apartment thinking: this. I want to fund this life by knowing things and going places and being useful in ways that also involve not being poor.

I did eventually join the Foreign Service. I did eventually get the apartment, the postings, the passport full of stamps earned by purpose rather than wandering. And years later, when I left all of it to build something of my own, what I was building was shaped — more than anything — by that rooftop. By the 3am streets of Cairo. By the Palestinian election poster I stood in front of without knowing why it mattered. By the woman with the wine and cheese who simply was what I wanted to become.

Sojourn & Soirée exists because of Cairo. Because I believe, deeply and without reservation, that the places we go — when we go to them fully, without armor, without an itinerary that insulates us from the unexpected — have the power to change not just where we've been, but who we decide to be.

The roof was sweltering. I wouldn't trade it for anything.

Planning a journey that actually changes you? Explore upcoming editions at sojournandsoiree.com.