Seeking Serendipity

why I still live in ny · Aug 21st, 2019
You Are What You Love · Chance Encounters · Defining Serendipity · Active Waiting · Finding Community, Finding Home · Anticipation · The Magic of the Web · Fear of the City · Sanctifying Time · Surrender

For this post, I adapted my thoughts from last month's "stream of consciousness" newsletter that I write for my supporters!

I wanted to share something that feels impossible to quantify at times: why we love (or learn to love) someone, something, or in this case, a place.

You Are What You Love

Over the last year, a number of people have asked me why I decided to stay in New York instead of living in another city, moving back home, or even becoming a “digital nomad”. It’s an appropriate question, especially right after I quit my job over a year ago and unsure about what was going to happen next.

It got me reflecting about why anyone dreams of moving to the city, let alone settle there.

In so many recognizable ways, it makes no sense. Living here causes me to think differently about how I live: how I spend my time and money. Maybe it’s working multiple jobs, taking public transport instead of getting a car, cooking instead of eating out, rooming with people instead of getting my own studio, living farther from the city, and simply having less stuff. Is it worth putting up with all the effort, sacrifice, and inconvenience?

It turns out that for me, it’s been worth it all. And I can confidently say that because of how well I’ve meshed with one particular ethos of the city: that we care about work too much (for better or for worse).

But is that any reason to stay, when I've left my job and could go anywhere to work?

Chance Encounters

I think the city compels a real, visceral reaction from anyone that comes.

"Why not?" is too nonchalant an answer to be convincing. Without some conviction I'd be forced to face reality and leave.

On paper it doesn't look so great either. I've told myself a number of rationalizations for the typical negatives of NYC: unpredictable weather ("I like having real seasons”), the busyness and hustle (“the city is alive, and I feel it as well”), the huge crowds (developing a sixth sense to stay away from Times Square), the noise (justification for buying expensive headphones), the smells (okay there’s no silver lining here), the high cost of food/rent/activities (developing money management skills). In that light, no wonder people here can be so jaded.

I wouldn’t always describe NYC as a hustle-filled, busy-bodied, anxiety-inducing place (it certainly can be for me), but instead it’s often an invitation for variety. The fact that people are too busy with their own lives means it can simultaneously feel lonely while a sense of solidarity persists, especially in times of strife (a recent example: when volunteers helped direct street traffic during the recent power outage). Everyone seems to have this unspoken, shared understanding of the struggles of life here. There's a certain conviviality in the atmosphere regardless of the borough I'm in; it's also embodied in the people inhabiting it.

So I’m led to the conclusion that my reasoning (which I would consider a feeling) must come from a nebulous quality about living in an urban city. Something that can somehow override all those evident negatives.

I’d describe it as a deep sense of awe and wonder. Because of the occurrence of so many "chance encounters" during my travels this past year, I couldn’t help but notice that what I was looking for was something I'd forgotten about until moving here: serendipity.

Defining Serendipity

It's something that is both unexpected and fortunate. It’s what I didn’t even know I was looking for but goes beyond my imagination. We can't force it; it happens to us and makes us feel alive.

..serendipity, which is the chance encounter that leads to a longer, richer interaction with a topic or idea. It’s the way that a metalhead bumps into opera in a record store, or how a young kid becomes interested in history because of the book reviews that follow the box scores. It’s the way that a course taken on a whim in college leads, unexpectedly, to a new lifelong pursuit. -Engagement is the Enemy of Serendipity

Active Waiting

Now that I’ve named it, I want more serendipity! Is it something that I can grasp or “take” more of? Or does attempting to strive and use effort to make it happen go against the whole point? I think not!

"..but a lot of times there is repetition. I claim that luck will not cover everything. And I will cite Pasteur who said, 'Luck favors the prepared mind.' And I think that says it the way I believe it. There is indeed an element of luck, and no, there isn't. The prepared mind sooner or later finds something important and does it. So yes, it is luck. The particular thing you do is luck, but that you do something is not." -"You and Your Research"

Most of us recognize the importance of preparation in many aspects of life. But does working towards that which isn’t guaranteed even desirable? I would say yes! We must face all sorts of unknowns in this life. A commitment to something isn't only helpful, but required to make sense of any of it. We risk failure, loss, reputation with the hope for a surprise.

I'm learning that the kind of intentional exposure in continually putting myself out there opens up possibilities for greater personal connection with people and the world.

Finding Community, Finding Home

I'm a part of some great communities here: my church, my (previous) co-workers at Adobe, and tech communities like BrooklynJS. And there’s always opportunities to discover new ones - most recently for me were groups like the ping pong crew at Bryant Park and the greater creator/startup scene in the city thanks to Patreon and Stripe.

It’s simply amazing how it things can tie together, how relationships can be formed so organically.

An example with my interest in ping pong:

And this past summer, we were able to catch up and play again when he had an opportunity to visit!

And a few months ago I stumbled upon this award-winning documentary about the ping pong tables at Bryant Park: The Tables (15 min).

It was so inspiring to hear the stories of the kinds of people who play there. In some sense, the conditions aren’t ideal at all: it’s outside (the wind, hot/cold temperature), the tables/net are metal, and there are random people everywhere. But yet there’s a thriving community there. People from all walks of life show up: those who work in the buildings around the park taking a lunch break, others that are homeless, visitors/tourists on vacation, or even locals (like me) who have lived here for years without realizing the tables were there. It was so cool to see and convinced me to check out the community a few times since then; I recognized a few of the same people in the documentary and even had the opportunity to play & chat with them.

What that community helped me see was this idea that I could be a part of a long-standing group that doesn’t even have formal membership and yet is sustained. The fact that I could go to the same place and expect people to be there without contacting anyone ahead of time or planning anything out is so special. It’s like a hangout place (a cafe, someone's place) with the same group of friends week after week, but with a shared understanding that someone will be there.

A place where I don’t simply know of others, but I am inexplicably known by them.


“There are no ordinary people. You have never talked to a mere mortal. Nations, cultures, arts, civilizations - these are mortal, and their life is to ours as the life of a gnat. But it is immortals whom we joke with, work with, marry, snub and exploit - immortal horrors or everlasting splendors. This does not mean that we are to be perpetually solemn. We must play. But our merriment must be of that kind (and it is, in fact, the merriest kind) which exists between people who have, from the outset, taken each other seriously - no flippancy, no superiority, no presumption.” - C.S. Lewis

I've noticed more and more, every month there's a handful of times where I see old friends, people at meetups, coworkers on the subway or during a casual stroll outside. Like Devon, I’ve started to use my calendar to record the past. And when I meet a friend unexpectedly on the street, I mark it with an 👀 emoji to remember the occasion!

I think back to the day before my trip to Romania in April. I was taking the subway home from a friend's place and randomly bumped into a middle school buddy visiting family at the 72nd St downtown Q station.

On another trip to Boston, I checked out a sister church of ours for a prayer meeting, and recognized the same friend I had met there two days later while wandering around for lunch!

And these opportunities don’t just come for people I'm already familiar with! I became one of those people willing (though not always initiating) to talk with strangers on flights. Even on a recent Amtrak ride back to NYC from Boston, Yusuf started a conversation with me by asking about my headphones and eventually we really connected in talking about faith and tech. As he says, “It’s not a coincidence that we met!”.

Maybe I shouldn’t be surprised that the probability of bumping into someone is fairly high, it's a dense city after all. But there's also so many people, so many things to do at any time of day, without knowing anyone's schedule.

I wonder how often I've passed by someone I know but was too preoccupied to notice?

The Magic of the Web

Experiencing serendipity in the physical world makes me wonder how it's fostered in our digital lives.

Recently I asked for some help with Stripe support. I was surprised to get some amazing help but also the response: "It's pretty cool to meet someone who helps maintain Babel! -- I'm actually learning to be a web developer now, and I'm in awe of what you guys do."

Sometimes it's as simple as the chance to meet (email) anyone in the world.

As a recent example:

After Nadia wrote about her thoughts in reading "The Death and Life of Great American Cities", I was really intrigued at the last chapter. I stumbled upon the guest of our last podcast episode on cities, Timothy, by essentially searching for someone who had written from a faith background on the subject using Google.

His paper, “The City as Liturgy” resonated with me so much I finally had the courage to send a cold email. To my surprise, he was so enthusiastic to talk! In my understanding, getting a random email from someone (entirely outside your field or group) that is super invested in what one cares about means a lot.

Soon after I had a chance to visit him in Boston! All that to say that being able to access so many people around the world does have some amazing benefits.

Fear of the City

Despite all that, we constantly hear (even from myself) the audible sighs that remind me about the perils of living in the city: the loneliness, the performance anxiety, the impending doom. It's almost as if we turn and use the city as an excuse for our issues and long for an escape away to greener pastures. The city itself loses respect and becomes our scapegoat.

Instead of time healing all wounds, the grind hardens our hearts. We feel defeated by the environment. Being jaded is now the default.

The openness to connect fades away. Our outward focus to relationship and to others folds in on itself. We become skeptical of the world and those around us.

I remember a friend in my small group shared about a fear of sharing life, making friends, and being vulnerable because you never know who is going to stick around. People leave in a year, stay for an internship, move back home. Why should we put in the time and effort to make relationships in the city then?

But should we continue to live in doubt? We do it anyway.

"I can’t be an idiot, but I would rather be duped from time to time — and pay that price — than become a person who lives in mistrust. When I get duped, I just chalk it up to the rent I’m paying for not living on Planet Suspicious." - Abigail Disney

At the same time, we try so hard to manipulate the world for ourselves, to innovate and replace rather than maintain and preserve.

"More is better" permeates the world. Everything is measured in utility, a specific from of purpose. It seeps into our sense of self, where to have more is to be whole. Everything becomes another form of measurement and optimization. We tend to think of silence, boredom, and quiet to be negative things in our distracted, technological age.

"Engagement is about avoiding silences, eliminating boredom, filling every moment with some exchange of my attention for someone else’s profit—with the promise that it will be better than one of those moments of silence and boredom." -Engagement is the Enemy of Serendipity

We tend to find ourselves keeping busy, which I’ve discovered to be a form of sloth. Laziness isn’t only a habit of not doing anything but an indifference to life, a spiritual condition of not caring.

But we feel this way because we don't actually want to think, to contemplate the issues facing ourselves. We need the space to allow ourselves to step back, where serendipity is fostered. As designers harness the power of space in user interfaces and art, we could take note to do the same in other areas. Notably with our time.

Sanctifying Time

Our hearts are restless, until they can find rest in you. -Augustine

Can we learn to see our time as not flat (not all the same), but meaningful, even sacred? That being productive isn't about getting from A to B faster and "doing more" but experiencing more of what life gives us, of being fully alive?

"People always believe they save time by taking a taxi. Let's say you take a taxi and it takes 10 minutes when walking would take 20. Mathematically, you save 10 minutes. But in those 10 minutes in a taxi, you didn't experience anything." -"Why Walking is the Key to Being More Productive"

We’re a people that tries so hard to be productive, to make it to the next job, school, step in life. It's in the city that never sleeps that we must practice intentional rest.

The Sabbath. The way we stop a cycle of overwork, burnout, anxiety may in the end be a stand against its goals entirely. To not do. A place where there is no striving or proving for a place. A place where we belong, our home.

I'm reminded of a book I read earlier, "Liturgy of the Ordinary" by Tish Harrison Warren, which asks: How do we "embrace the sacred in the ordinary and the ordinary in the sacred?" The author shows how the minutiae of daily life can be a source of joy as well as depth. Even the first chapter, Warren presents the simple act of waking up in the morning as a daily reminder of learning to be beloved by God.

When she wakes up tired and vulnerable, without any identity she has given herself (a child, friend, mom, employee, citizen, etc), God delights in her despite not having done anything. She gets up remembering her identity in Christ is given rather than earned.


Despite it being freely given, does serendipity "ask" anything of us? We need to leave "room" for it to show up: with our time, with where we are, with our thoughts. It's planning to be unplanned, to expect the unexpected.

There's no formula here, no obvious cause and effect. It goes beyond the notion of making use of our time productively. What's needed is downtime, free play, day-dreaming, the capacity to imagine again.

It asks more than we might realize at first. It calls for an act of surrender rather than an act of volition. We lay down our specific plans, strongest desires, and indomitable will in a hope unseen. We know in seeking serendipity that nothing is guaranteed, and yet we still commit to it. Why?

Because we experience a gift beyond what we expect, one that we understand we can’t attribute to our own doing. We realize that we aren't the captain of our souls and are humbled yet free. Serendipity, especially through the city, has shown me that life is all by grace, undeserved and yet somehow ours. I didn't even know it was what I was looking for, until it found me.