It’s okay to be a lonely, anxious mess, and more things I learn.

Samantha told me her secret of country life while we lay sprawled on a picnic blanket at sundown.

We were at an outdoor concert in the Berkshires in Western Massachusetts. Musicians weaved past picnickers on their way to the stage. Strands from a bamboo flute drifted by, snatches of drums, a man playing a moon-shaped lute. We’d both had some wine.

“Since I moved here,” Samantha whispered, looking sneaky, “I’ve come a lot closer to death.”

“Me too,” I said, beaming over at her. Finally, someone had said it.

“It’s the mountains, I think.”

“They’re so big,” I said. “And we’re so small.”

“And it’s so quiet, all of the time.”

We watched our friends divvy up a wedge of Brie a few feet away. It occurred to me, not for the first time, that I might have to stay in the Berkshires for the rest of my life. This was a scary thought, but I was getting used to those. I reached for some cheese.

***

When I moved to the Berkshires at age 28, I was overflowing with worries about the life decisions I’d made: deciding to move across the country to go to grad school, and then deciding, after three years, to drop out. Some recent tumult in my romantic life didn’t help, either. “You remind me of Pig Pen,” one friend said to me at the time, referring to the Peanuts character surrounded by clouds of dirt. “But instead of dirt, it’s chaos.”

I was embarrassed about my own indecision, scared about what I was going to do with my life, and convinced that all my peers were judging me. So I moved to the Berkshires—the only place I could find a job—and began to marinate in self-doubt and existential dread. I didn’t know anyone who lived there. All the coffee shops closed by 6 pm. It was the Bermuda Triangle of cell-phone reception.

People love the country because having plenty of space to think and move around sounds like a good way to reduce stress. But the downside of living in a place where you feel outnumbered by cows is there are fewer distractions from your anxieties. The country did force me to just be; but that was a hard task, at first, because what I was back then was kind of chaotic.

In the quiet of the mountains, I felt like I could suddenly hear everything—the tapping of a woodpecker and the wind rustling the leaves of the oak tree outside my bedroom, yes. But also every insecure thought swirling around in my head. And in order to get comfortable with the realities of my life, I needed to let those scared, angry, worried voices finish what they had to say.

***

My first few months in the country were ablaze with positive thinking. I finally taught myself how to ride a bike, wobbling in loops around an empty parking lot before braving the roads. I took up a lot of complicated DIY T-shirt projects. I got a regular gig writing features for the local paper and drove around interviewing townspeople about their various occupations—a three-generation family that sold silk-screened calendars, a woman who'd written a cookbook about how to make pop tarts and pickles.

The area wasn't overflowing with young people. But I hit it off with Samantha, a whip-smart librarian with a collection of perilously high heels, and her genial, sarcastic husband Jim. They'd moved to the Berkshires from Chicago the year before, and were equally startled to find themselves in a place so heavy with silence. We split orders of fried pickles at the local pub and forged our way to a Halloween party at a historic tavern in the midst of an early-fall snowstorm.

Was this the life I'd imagined for myself in my late twenties? It was not. But I was doing fine—right up until winter fully descended. Shut up indoors and hiding from frostbite, I suddenly noticed that I was super lonely.

And while I’d imagined that the ruminative beauty of a New England winter might get my creative writing juices flowing, in practice I found that being alone with my thoughts sent me into anxiety spirals.

Cooped up with my computer and endless cups of coffee, I thought about how isolated I’d become, and how it was all my fault. I'd taken people and lucky breaks for granted, and walked away from good things just because the possibility of something even greater was waggling in my peripheral vision. As past complaints came to mind, I composed lists of all the things I wished that I’d done differently on spare scraps of paper throughout the day, the way normal people jotted down groceries and errands.

“Not standing up for myself enough,” I scribbled on the back of a pharmacy receipt. “Caring too much about other people's opinions,” I wrote in the margins of my notebook during a meeting. “Leaving New York. Grad school, of course.”

It was a pretty cool hobby. The problem was, I couldn’t locate any kind of roadmap for people who were convinced they’d ruined their lives by being too dumb to understand what they wanted. Why weren’t more humans talking about this?

There were some novels and movies and TV shows about regret, but they didn’t tend to be very solutions-oriented. Walter White regretted losing his chance to be a successful millionaire, so he became a meth kingpin. Mr. Rochester regretted marrying his first wife, so he locked her in an attic and thumped around shouting at governesses unexpectedly. These were not helpful role models.

The most practical advice I could find on regret came from a TED talk by a woman who wished she hadn’t gotten her tattoo of a compass rose. Her words of wisdom boiled down to “give it time." This made me feel desperate and impatient, so I went in the other direction. I decided to make myself so busy that time would disappear.

***

Samantha, Jim and I began going to trivia night at a bar near their house. Each Wednesday we'd gather to sip pints of PBR and hiss the names of dead presidents and early rap songs under our breath, so our competitors wouldn't hear.

We got to know the other regular players: a solitary man rumored to have swept Jeopardy twice back in the 1990s; the local mycologist, who smuggled in flasks of black-truffle vodka that he passed around under the table.

In the summer, I joined a community garden, and spent eight hours a week crouched over rows of purple string beans that grew long and bumpy as witches’ fingers. I was intimidated by the graphic designers and jewelry-makers who worked in the garden with me, all casually beautiful in an Oil Method way and knowledgeable enough to know that dead-heading was an action unrelated to Jerry Garcia. After a while I felt comfortable enough to swap pickling techniques and calendula skin treatments with them.

Dating! I was doing that too. Pickings were slim in the Berkshires, but I gave it my sporting best. I went out with a painter, a political aide, a teacher, a lawyer, a couple of journalists. My favorite was an adorably discombobulated reporter who swore a lot, loved The X-Files, and was launching a deep-dive investigation into the recent surge of bobcat sightings in Western Massachusetts.

But mostly I filled my time by working. In addition to my full-time job, I had a pop culture blog with a few friends and was freelancing for more than one paper. And after a while, I took on a recurring gig that transformed my social life: I started taking party pictures.

The job was pretty straightforward. Once or twice a week, I'd drive out to a hospital fundraising gala or a retro-space-themed dance party. Then I'd march up to strangers, brandishing a camera and a notebook, and ask if they minded if I took their picture. Most of the time—much to my surprise, at first—they didn’t.

I learned picture protocol fast. Shoot from the waist up, no more than four people at a time. In group shots, get everybody's arms inside the frame, or else they’ll look like sock puppets. When a party guest gives a goofy fake name, laugh obligingly. (This last rule sometimes backfired. Early on, a smiling man in a suit told me his name was Smitty Pignatelli. I chuckled and asked what his real name was. Smitty Pignatelli was his real name, and he was our state representative.)

Taking photos gave me an excuse to slip inside the worlds people had made for themselves in the Berkshires. So this was what everyone had been up to that first isolated winter, while I padded around writing myself recriminating notes on napkins! There were artists' retreats in converted barns that culminated in raucous dance parties; buffet dinners spread out on the terrace of Edith Wharton’s gabled home in Lenox. I snapped pictures of farmers’ brunches and bluegrass concerts, art openings and Halloween parties in tents stacked high with local gin and bales of hay.

I loved talking to Berkshires natives and transplants at these parties, learning how they’d started their own nonprofits and breweries and theater companies. Of course, a lot of people had had money to begin with, which played an important part in determining whether they could make a go of becoming a handbag designer or green juice guru. But some of them hadn’t had much, and still didn’t. This was a place where people could try to reinvent themselves. And the longer I stayed, the lighter and steadier I became. I was less worried that I’d die alone and unfulfilled in the middle of an ice storm, and more confident that I might be able to grow into a different kind of person.

***

Part of the reason I’d been so miserable in the Berkshires that first winter was that I’d worried my loneliness there would be permanent, it would never change. It was an easy thing to believe, trundling down picture-postcard streets that looked like they hadn’t altered a brick since Norman Rockwell painted them in 1967.

But the longer I lived there, learning new names, accepting and extending invitations, erasing one set of memories in order to make room for the next, the more I understood: I couldn’t even stop change if I wanted to.

Almost two years after I’d moved to Western Massachusetts, I began looking for a new job in earnest, and I caught a break. Within a month I was in New York, a city I'd left once before and missed ever since.

The day I moved back to the city, I thought about that old Frank Sinatra chestnut: If you can make it here, you can make it anywhere. But the truth is, making it—building a big, messy life for yourself that you can be proud of—is a plenty hard job any place you might go.

After years among those mortality-evoking mountains, I still felt small, but not scared. I was ready to start over. I already missed trivia night and wading down rivers and sun-warmed tomatoes and all my old friends.

Standing on the deck of my new apartment, listening to the roar of the Brooklyn-Queens Expressway, I imagined a woman like me, 150 miles away in the Berkshires, carrying her first box of books into a farmhouse. I felt like she would: Just lucky to be there, lucky to choose.