On Leaving, Returning, and Beginning Again

On Leaving, Returning, and Beginning Again

After years spent arranging the lives and travels of private clients, I took a year for myself, exchanging endless requests for Swiss hotels, Italian wine country, and the freedom to write. I discovered that being on the other side of luxury hospitality could teach me a few things about my old profession, and about myself.

I have always maintained that one of the great pleasures of traveling is staying in a beautiful hotel, preferably one where someone else is responsible for the laundry. I enjoy museums and restaurants as much as anyone, but there's something rather civilized about ordering room service and having absolutely nowhere to be.

After nearly a decade working in private service, most recently supporting one of the world's most prominent family offices, I had become rather accustomed to making other people's lives run smoothly. The requests could be wonderfully specific, the expectations extraordinarily high, and the hours occasionally absurd. For almost three years, fifty-hour workweeks had been my normal, and I had spent much of that time arranging the sorts of experiences most people only encounter on holiday.

So when I decided to take a year away to travel through Europe and write two novels, my ambitions were relatively modest. I wanted to stay somewhere beautiful, eat extremely well, finish my manuscripts, and remember what it felt like to have no one else's schedule to manage.

Naturally, things didn't go entirely according to plan.

Zurich

My first stop was The Dolder Grand in Zurich, a hotel whose scale and beauty left me momentarily speechless. Its grand architecture and views over the city were remarkable, but I was just as taken by the life unfolding within its walls. Children wandered through the corridors, families came together over meals, and strangers moved past one another, each carrying an entire world of experiences and concerns that remained invisible to everyone else. I loved being among them, observing these passing glimpses of other lives while feeling, for the first time in years, wonderfully removed from the demands of my own.

Some afternoons, I barely left my room. I would order something with a French or German name that required a little research, enjoy my meal at whatever pace suited me, and allow the afternoon to pass without consulting a schedule. After years of being responsible for so many moving parts, I found the absence of urgency both delightful and surprisingly difficult to get used to.

From Switzerland, I made my way to Casa di Langa, a secluded resort in the hills of Piedmont, where vineyards rolled across the countryside and the days seemed to pass at their own pace. I had imagined it would be the ideal setting for my novel: quiet mornings, hours of uninterrupted work, and enough time afterward to enjoy being in Italy.

Instead, I found myself increasingly content to do very little. The food was delicious, the wine plentiful, and the people possessed a warmth that made even the simplest interactions a pleasure. There was something about the place that made the usual concerns of daily life seem very far away.

Tyler Moses

The experience taught me something I had been trying to articulate in my novel: that there is value in simply being without the constant pursuit of something to show for your time. Away from the measures of a productive day, I find myself paying closer attention to the experience of living rather than what I might accomplish. In a foreign place, stripped of routines and expectations, you are left with the curious experience of being both a stranger to your surroundings and newly familiar to yourself. I accomplished very little writing in Langhe, but what I experienced there eventually made its way onto the page.

From Langhe, I continued to Florence, a city whose beauty I could appreciate considerably more than its crowds. The streets were filled with students and tourists, everyone seemingly in a hurry to reach somewhere of equal importance, while I was left navigating a steady collision of shoulders and overlapping conversations. I did not enjoy Florence.

Vienna, however, was another matter. I eventually rented an apartment and spent my days wandering through its seemingly endless neighborhoods, walking for miles with music in my ears and no particular destination in mind. I discovered little cafés, galleries tucked away on side streets, museums alive with visitors, and strangers willing to share a conversation. I ate long lunches alone in beautiful hotel restaurants, feeling only occasionally self-conscious about it, and dated men whose troubles ranged from an ordinary fear of commitment to father issues that seemed to warrant professional intervention. Somehow, between the solitude, the encounters, and the occasional romantic misjudgment, Vienna began to feel like home.

I continued taking short trips, following my curiosity wherever it led. Dublin gave me towering cathedrals, satisfying meals, and crowded pubs in which laughter carried over the conversations and I made another unsuccessful attempt to appreciate beer. Ballyglan offered a few days of green countryside and near-total seclusion, interrupted only by the discovery that visiting the nearest town required arranging transportation an hour beforehand, an indignity I still remember. And then there was Lisbon, which remains one of the places I return to most often in my thoughts. There was something about its colors, its food, its people, and the simple pleasure of walking its streets that made me feel less like a stranger than someone returning to a place I had somehow known before. Porto, with its … grittier streets, did not inspire quite the same affection. But I came away from all these places with more than memories. Away from the relentless expectations of my working life, I began to recognize parts of myself that had been neglected for years, not lost so much as waiting for me to pay attention.

Tyler Moses

When I eventually returned to the United States, suffering from the post-vacation blues and missing those European water bottles with the caps that stay attached, I had every intention of finding another job.

Instead, I accidentally became a founder.

I began by writing about my travels while searching for my next position. I revisited the hotels I had loved, the places that disappointed me, and all the small details that had distinguished one experience from another. It reminded me of the information I had spent years gathering in private service, much of it scattered across documents, emails, and conversations I could no longer entirely recall. A hotel's or restaurant's reputation was easy enough to establish. What mattered was knowing the particulars, the things you discovered through experience or by asking the right questions, and having that knowledge available when you needed it. I started organizing those details for my own future reference.

That little exercise became Averrin.

I became interested in the difference between knowing that a place was worth visiting and knowing precisely what could be arranged there. A restaurant might have a private room no one thought to advertise; a hotel might be able to accommodate a request that seemed impossible from its website; an experience might be entirely different when arranged through the right person. I began writing to providers directly, and what started with travel soon extended into the many services that support private households and their daily lives. I wanted the people doing the work I had once done to have those answers before they needed them, rather than spend their days trying to discover what someone else might already know.

When I consider everything the past year has brought, what astonishes me most is not how far I traveled, but how far I allowed myself to go. I had spent so much of my professional life making things happen without being seen, and suddenly I was putting my writing, my ambitions, and my ideas in front of people whose judgment mattered.

There is a peculiar vulnerability in creating something that belongs entirely to you, because criticism of the work can feel inseparable from criticism of the person who made it. This year, I had finally allowed myself the possibility of failure, which also meant allowing myself the possibility of becoming someone I had never quite dared to be.

I had gone to Europe to write, to travel, and to remember the pleasure of having a life that belonged entirely to me. I finished my novels, fell in love with places I had never seen, and found that I was capable of much more than the work I had allowed to define me.

The year came with its share of uncertainty, difficulties, and frustrations, but it also gave me something I had not known how to ask for: the freedom to become myself.

With perseverance, a little success, and the occasional kindness of circumstance, perhaps the coming year will find me at The Dolder Grand once more.

Article by Tyler Moses

Tyler Moses is a writer and the founder of Averrin, an international provider-intelligence platform for professionals supporting private clients.