In Search of Serendipity

Three years ago today I moved into my place in Fort Point in Boston. It’s the first place I’ve ever owned. I moved in in a snowstorm. My friend Loryn hiked over in her ski gear that night to celebrate with me. I’d moved out of the Back Bay apartment I’d shared with my long-term boyfriend for almost three years. We’d lived together in Brooklyn before that and in Watertown before that. I wasn’t quite 25 when we started dating. And I moved into my new place at almost-34 with the same furniture I’d owned when I first met him: my mattress and my dresser. Loryn and I sat on the living room floor and drank Veuve out of the bottle. It would be two more days until my glassware arrived from Crate and Barrel and a couple of weeks until my Room & Board couches showed up. I loved everything about my place. I loved scrubbing the painters’ footprints off the wood and wiping the bathroom vanity every time I washed my hands or brushed my teeth. I finally understood why my mom had followed all of us around with a vacuum and a roll of Bounty for 18 years. I was psyched to make this place as perfect as I could. I was ready to make it mine.

Three months ago today the guy I fell for left. And from that night on, when I looked around my place, all I could see was what was gone. Guitar case absent from its resting spot behind the recliner. Toothbrush missing from the holder. Clothes disappeared from the closet and the pile beside the bed. For the first time in almost three years I didn’t feel good here. I stayed on friends’ couches and in my parents’ spare room so I didn’t have to sleep in my own bed. I went on work trips. I went on vacation. I wondered if I’d ever feel at home again.

Four days from now I leave for Seattle. When I tell people what I’m doing their first question is usually: “Why Seattle?” I have a number of answers; some feel more true depending on the day. It’s a city I love. It indexes high on rowing and low on snow. It’s a way to geographically force myself out of ruts and unhelpful patterns I’ve fallen into. I know just enough people not to be lonely, but not so many that I won’t be forced to make new friends. …and maybe everybody’s wrong and you can run away from your problems?

But I think the most true answer is the one I don’t usually say out loud: I’m going in search of serendipity.

Which is the most dumbass thing in the world to do.

I remember the most furious I ever got at a work event. It was years ago at a panel featuring a bunch of tech/marketing guys who were all hawking their latest apps. A kid named Seth was on the panel and his goal was to create “a serendipity engine”: a data-driven, always-on virtual reality experience that would overlay every move you make. Your phone would get super smart about what you liked, what you were interested in, who you were friends with, and it would start to ping you in real time throughout the day when the data suggested you might like something around you. You’re walking down the street, about to pass a hole-in-the-wall restaurant you’d ordinarily stroll by, and PING. Data suggests you should stop dead in your tracks and try it. A sunset view is just out of sight, but if you head left and walk twenty five steps, 99 out of 100 friends agree it’s worth a look - PING. So you turn and start walking.

I. Was. Incensed. I skew technophobe anyway, and this idea just rubbed me raw. I waited till the Q&A, stood up, and asked: “Do you worry that if this gaming layer actually gets built, and this technology does start to control each move we make and each thing we experience, serendipity is actually the thing that will go away forever?” Seth didn’t seem to understand the question. He moved on to someone else.

And now here I am, ten or so years later. Pot. Kettle. Black. The truth is I booked this trip to Seattle a couple months ago because I want something to happen to me. I don’t know what. Something wonderful. Something transformative. PING - hang the next right, say yes to this opportunity, smile at this person, and BANG. I’ll feel good again. I’ll feel like myself again.

I’ve been thinking about the moments of serendipity that, in hindsight, have shaped my life. And how all the moments where I thought I was in control - the moments I felt I was actively conjuring fate - were just rest stops on the way to the actual situations where something meaningful happened. I was sure that my move to Hollywood at 22 years old was the moment that would unlock my career as a screenwriter. I was devastated when, less than a year later, I was back home and completely clueless about what I actually wanted to do with my life. Two months later I was working at my first advertising agency. They were the only agency that had responded to the twenty cover letters I sent out. It was a shop run by a failed director and a failed actor. I found out later they only hired me because they saw Hollywood on my resume, and they thought I could get their movie project in front of someone who mattered (spoiler alert: bad strategy). Fifteen years later, advertising is still the industry I work in and love.

At seventeen, after my first trip to California, I was sure that Stanford was where I was destined to go to school. When I didn’t get in I was heartbroken. I decided to go to Harvard because - and only because - I thought it would give me the best shot of transferring to Stanford the following year. I told the bookstore I only needed a one-year membership. I didn’t bother filling out course preferences for sophomore year. I mailed my transfer paperwork in late October and I waited. And as I did…things started to change. I couldn’t get enough of this strange new rowing motion that my body was learning. The thought of leaving my new friends made me hurt. I started to take the long way home from class, walking an extra loop through the Yard when the trees were beginning to turn. And today I have my best friends in life and the sport that I love because of the place I was sure would be my one-year, brick-clad waiting room as I made my way to where I was meant to be.

Seattle is the biggest, most deliberate change that’s come from that awful time in November. But a lot of little things have changed, too. I’ve started writing again - and I’ve heard from so many friends that I thought I’d lost touch with years or decades ago. I’ve started reading books about Buddhism, and how to find joy and peace when you’re struggling and feeling groundless. I’ve spent more time on the phone with my family. I’m a noob meditator. I’ve gotten a little better at asking for help. Who knows whether any of these will prove to be “the thing” that helps steer me towards where I’m meant to be next. (Maybe I should actually pay attention to my Buddhism books and stop looking for an effing “thing.”)

Last night I was supposed to start packing. But instead I walked around my little place and took pictures. Of the art on the wall. The photos and cards on my bookshelf. The little trinkets from travel I’ve collected over the years. So that I can keep a piece of them with me when I’m away. Because I can start to feel that, as excited as I am to go, I’m going to miss my home.

It wasn’t the feeling I’d been deliberately searching for. But I’m glad that it found me anyway.