“You are at the center of a mystery. It is a mystery of love and of time. And it is the only story worth telling.”

-Andrew Sean Greer, Less

In March 2022—somewhere between “lockdown” and “return to office”—I found myself in San Juan, Puerto Rico, standing in front of a group of mostly strangers, giving an impromptu talk titled “How Woo Are You?” The setting was a co-living community. The event was called fake church. And while the speech itself is a story for another day, the real question is: how did I end up in that particular place, at that particular time, doing that particular thing. 

It’s a journey story. And if you know me—or this blog—you know I love a good journey story.

This one started five and a half years earlier, in October 2015, when I left my job at OpenTable after nearly a decade. I had lined up my next role at Metromile, but I’d negotiated a three-month sabbatical in between. One of my goals was to write more (some things never change), so one sunny day during that break, I planned to take my laptop to a neighborhood café to do just that. Before heading out, however, I opened a piece of mail from my future employer that included a Metromile sticker and, without much thought, slapped it on my laptop. 

The cafe was packed, but I snagged a four-top and settled in. A few minutes later, two women asked if they could sit down since no other tables were free. After quick intros, one of them, Andrea, noticed the recently placed Metromile sticker and asked if I worked there. Despite the fact that Metromile was still a fairly unknown startup, it turned out that coincidentally, she knew an executive there. That small-world moment sparked a conversation, and that conversation turned into a friendship.

Fast forward about a year, we were back at the same café catching up when Andrea said, “I went on the most amazing trip to Israel. You have to do it.” She explained that there was a nonprofit based in Oklahoma that organized ten trips each summer, taking groups of fifty people to Israel to learn more about the country. The trips were organized by interest, and one of them focused on tech—which is the one Andrea had gone on and the one she eventually convinced me to apply for.

Like many things in my life, I approached the application with a healthy dose of procrastination and a complete lack of expectation. I submitted it the night it was due, including a short essay and a barely thought-through video where I rambled about being curious, loving new experiences, and having absolutely no connection to Israel whatsoever. Miraculously, I got in.

So in the summer of 2017, I found myself at the Tel Aviv airport, boarding a bus with forty-nine strangers. (To be honest, at that moment I was questioning the intelligence of saying yes in this particular instance, but given a lack of viable alternatives, boarded the bus and took a seat.) A woman sat down next to me and introduced herself as Gillian. I have no idea what we talked about as we headed to our first activity (which, as an aside, was a goat and sheep herding competition), but that conversation turned into a friendship. 

One of the things I learned about Gillian over time was that she had always dreamed of creating a co-living space—a big, shared house full of intentional community. Unlike most people, she actually did it. She moved to Puerto Rico shortly before the pandemic and established a co-living home in San Juan. So that is how, a few years later, with remote work still the norm, Parisa and I went to visit.

The house was busy—but in the best way. Ten people lived there full-time in seven bedrooms, with a few couples sharing rooms. There was a steady mix of short- and long-term guests, and the vibe was relaxed but thoughtful. People didn’t hang out constantly, but they genuinely liked each other. They’d share meals—usually loosely organized through WhatsApp—and they figured out logistics like bills, chores, and even car-sharing with remarkable efficiency. They also had a wide circle of friends who’d show up regularly for dinners, parties, and impromptu storytelling nights.

One of those storytelling nights was called fake church.

The idea came from a resident who said she wasn’t religious but missed the part of church where someone gave a heartfelt sermon or moral teaching. So the house created fake church: a rotating event where one person would share a story, ideally with a lesson or reflection, and then everyone would discuss. The first week in Puerto Rico, we sat in on one about a poet—Burke, I think—who specialized in the art of bleak realism. It was beautiful, surprisingly emotional, and completely different from any dinner party I’d ever been to.

Toward the end of our stay, they asked if I’d like to host a session. And—shocker—I said yes. Without (also shocker) thinking too much about it. Which is how I found myself in front of a group of people I mostly didn’t know, giving a talk titled “How Woo Are You?” in a tropical co-living house, because of a sticker I stuck on my laptop six years earlier.

“You can’t always get what you want / But if you try sometimes, you just might find… / You get what you need.”

— The Rolling Stones

I’ve come to believe that saying yes—especially when it’s not part of the plan—increases your surface area for luck. That sticker on my laptop. That crowded café. That spur-of-the-moment application. That half-baked speech at fake church. None of it was strategic. But every one of those moments opened a door to something else: a person, a place, a perspective I wouldn’t have found otherwise.

Which brings me to Arthur Less (finally).

Andrew Sean Greer’s Less, the 2018 Pulitzer Prize winner for fiction, is about a man who also says yes without a ton of forethought—mostly as a way to avoid dealing with things head-on. Arthur Less is a middling novelist on the verge of turning fifty. His former boyfriend is getting married, and rather than decline the invitation (and appear bitter) or attend (and feel worse), he accepts every literary event, half-baked opportunity, and far-flung invitation he can find: a teaching gig in Germany, a book event in India, a writing retreat in the Sahara, a wedding in Japan. What follows is a round-the-world trip full of misadventure, mistranslation, and unexpected grace.

This isn’t the first time I’ve written about saying yes. In my post about March, I complained—at length—about the novel’s protagonist, Peter March, who seemed constitutionally incapable of making an active decision. He wasn’t so much a character as a vessel of regret: a man who wandered into war, into marriage, into abolitionism, into fatherhood, and then wondered, decades later, how it had all turned out so badly. My frustration with March wasn’t just that the book felt inert—it was that its main character seemed allergic to agency.

Arthur Less is the opposite. He’s not exactly bold or decisive—he’s actually kind of anxious and bumbling—but he says yes. Not because he knows what he wants, but because he’s willing to find out. Less’s journey is made up of improbable moments – a misbooked hotel room, a shared cab ride, a stranger on a plane – that end up shaping his life. And his accidental yeses—clumsy, last-minute, sometimes entirely misinformed—end up opening his world in surprising ways. He connects with people he never would have otherwise. He discovers new dimensions of places and old relationships. And slowly, without meaning to, he begins to understand himself a little better. Not through reinvention, but through motion. Not through ambition, but through openness.

You’re not allowed to be fifty yet. That’s for people who have made their lives.”

— Less

At its core, Less is a comic novel about heartbreak, aging, and the quiet panic of irrelevance. Arthur Less is almost fifty, and he’s starting to feel like the world has moved on without him. His last book didn’t make much of a splash. His former lover is getting married. He’s invited to events where no one quite remembers who he is—or worse, they confuse him with someone else entirely. He worries he’s a footnote in the very life he’s still living.

Greer writes with a light touch, but there’s real sadness in Arthur’s self-doubt. He’s a man caught in that weird middle place between no longer young and not quite wise, unsure whether the choices he’s made have amounted to anything at all.

This isn’t a grand reinvention story. There’s no career triumph, no epiphany on a mountaintop. Instead, Less captures something far more honest: the low-stakes awkwardness of aging into your second act and realizing the only real solution is to keep moving forward. Or at least sideways.

In some ways it reminded me of The Stone Diaries, another Pulitzer winner steeped in the quiet tragedy of a life undervalued. But while Daisy Goodwill’s story was told in fragments, lost to history even as she lived it, Arthur Less’s story unfolds in real time—with all the confusion and comedy that midlife provides.

And of course, I couldn’t help but think back to A Visit from the Goon Squad—my post about time, memory, and the slow thievery of age. If Goon Squad was about how time steals, Less is about how time sometimes gives back. Not youth, not clarity—but perspective. And maybe that’s the better deal.

Time grabs you by the wrist / Directs you where to go.”

— Green Day, “Good Riddance (Time of Your Life)”

I think about that Metromile sticker a lot. About how easily I could’ve left it in the envelope, or sat at a different table, or avoided conversation altogether by putting on headphones like any normal café introvert. And then—no Andrea. No Israel trip. No Gillian. No Puerto Rico. No fake church. No sermon.

We make a thousand decisions every year that seem like nothing. We apply to things we’ll probably never get into. We say yes to a dinner that sounds sort of awkward. We get on a bus. We sit down next to someone. And those yeses—those tiny, throwaway, who-knows-maybe-it’ll-be-fine yeses—they’re what turn our lives into stories. Not always big stories. Not always neat ones. But real ones. And if we’re lucky, they bring us the people who make it all matter.

You don’t have to be certain. You don’t have to be fearless. You just have to be willing. Say yes, even when it’s awkward. Even when it doesn’t make sense on paper. Because sometimes, saying yes doesn’t just change your plans.

It changes your life.