why I left nyc
personal note
my story with new york didn’t exactly have a happy ending. a few months ago I decided to hand off my lease in williamsburg and go nomadic for a while, starting with a few months in san francisco. I wanted my goodbye to new york to feel heartfelt and optimistic, but instead it mostly felt rushed and numb. and in an ideal world, I never would have said goodbye to new york at all.
something I’ve written about is a desire for long-term friendships and stability. the first two years I had in new york I craved that, and then for about a year and a half I finally had it and I wanted to keep it that way forever, and I was sure that me and my good friends were all gonna stay in the same place until we got old—except that another year or two later, I felt about as alone as I had felt when I first moved here.
to be clear, I had an amazing life in new york. I had hundreds friends and acquaintances, I was hosting regularly, I had a variety of different interesting communities I was a part of, and I loved my roommates. and yet somehow, four and a half years into my time there, I would often go to sleep thinking, “what kind of life have I setup for myself here, and why do I feel so alone?”
I think the version of me from a few years ago would have hoped that after five years in new york, I would be so settled, have such deep roots, that the prospect of moving wouldn’t even cross my mind. but instead, I somehow felt like all the work I had put in to building friendship and community just…didn’t amount to much. let me try to explain what I found unsatisfying about it, while also recognizing that despite all this I’m still one of the luckiest people in the world to have the amazing friends and communities I have—
in new york, everything felt transient. I constantly met new people, only to never see them again. everyone packs their social schedule, which makes it hard to make spontaneous plans, and some people pack their schedule with multiple social activities in a single night, which makes it hard to have the slow, several-hours-long hangouts I prefer. despite all the work I did to create social spaces that were not just about drinking in dark and loud spaces, it still felt like the “center of gravity” for social life was drinking in dark and loud spaces. I hosted tons of events, but the overlap between “my close friends” and “people who attend my events” was frustratingly small. I had friends in very different worlds, which is nice—but it felt like the worlds they were in were too different, and trying to host one big party where all my friends would be in one place seemed like a recipe for awkwardness, and people not really “getting” each other.
the transience was what got to me. I’ve always wanted something very simple: a small group of close friends that I see consistently, week after week. friends I feel comfortable just sitting with. friends I can make my stupid absurdist jokes with, friends who will prioritize me by setting aside an entire evening rather than just “let’s catch up between 7-8pm three tuesdays from now.” I had a semblance of that kind of community in new york for a while, but by the end of my time there it was nonexistent.
now the question is—what do you do about this? you’ve found yourself in a situation where you don’t have the consistency and depth of connection you want. there are two strategies: start where you are and make incremental improvements; or blow everything up and start from scratch.
for the longest time I was implicitly trying the “incremental improvement” strategy, and at some point I gave up. I still believe that at the end of the day, this problem is in my control, if I’m willing to put in the effort. there is a parallel universe where I actually did create exactly the kind of community I wanted in new york, and I’m still there. it’s just that building such a community takes effort. and between my work, my hobbies, and the various other preoccupations and interruptions in my life, I did not have much energy left for building and maintaining a close-knit community of best friends.1
and this is where san francisco came into the picture. I came here for a month this year to try it out, and I was surprised to find that I somehow felt more at home here than I did in new york. hosting and making plans felt less effortful than it does in new york because people were open to making plans last minute, and people were down for “slow, relaxed” hangouts that might take up an entire afternoon or evening. also, more of my friends here are into the exact same things I am (writing, meditation, obscure intellectual rabbitholes), and the circles feel small enough that even when I bring together friends from different worlds, there’s enough common ground to have interesting conversations. I was enjoying my visit so much that I even pushed back my flight to nyc to get an extra weekend here.
that month in SF showed me that maybe it’s time to try out the “blow it all up” strategy. that, as disappointing as it is to admit, I never ended up building the “deep roots” I wish I had in new york. the life I had built for myself was something I was willing to let go of.
so now I’m in SF, at least for the next few months. I handed off my new york lease and got rid of all my stuff, and found a sublet here. rather than insisting that any one place is the place I’m gonna be for the next decade, I’m leaning in to being a bit untethered for a while. the end goal is still to find a place and community for the long haul, but I’m no longer insisting that I have to know where that place is right now.
however long I stay here, I want to make the most of it. I want to make every place I go to feel like home, whether I’m there for a weekend or for a year. I want to be “that annoying guy who keeps inviting you to things / asking you to hang out,” at least until I feel like I’ve found some consistency in the people I see.2 I want to prioritize my closest friendships and not spend all my time doing “quick catchup over coffee” with people I only see once a quarter. I want to befriend people who are down to be silly and goofy. I want friends I can grow with, friends who are willing to be there for me, but who are also willing to challenge me.3
even with the frustrations about friend-making that I’ve written about, I can see just how incredible my life already is. there are a large number of amazing people in the world—some of whom I already know well and some of whom I haven’t met—and I have the chance of building lifelong friendships with a small number of these people. I work remotely and get to live where I want, I can use the internet to connect with people and share my thoughts, and some people are actually willing to listen to me and join the conversation. I am young, healthy, and free. and I know that with the passage of time I will find the community I’m looking for.
addendum / practical notes
a few other notes I couldn’t weave into this letter:
if you’re considering a big move, consider one non-obvious benefit: shaking things up gives you better perspective on life, regardless of whether it ends up being the “right decision.” deciding to move helped me remember how temporary everything is. it forced me to have several cathartic “goodbye conversations” and get some things off my chest, and it also helped me realize that people appreciate me more than I had thought. in my last few weeks I saw more beauty in new york than I had in a while. I spent one of the nights of halloween weekend just sitting on the L train, riding it back and forth, getting off at random stops and walking around, appreciating how silly and joyful everyone looked.
also, if you work remotely, moving is such an easily reversible decision! before I did it, it felt like such a huge deal conceptually to move across the country but like, literally it’s a matter of packing some bags and buying a flight and maybe buying/selling some furniture off facebook marketplace.
it’s only been a week, but so far I’m loving SF. I’ve had lots of “cozy spontaneous hangouts,” like the other night when my brother invited me to a dinner with a few high school friends and we had dumplings and made vision boards. (also living with a sibling is so great, damn.) I organized a friendsgiving on very short notice and actually have a few friends coming that I’m very excited to see. I went to playspace (which was the original inspo for me to ping jaclyn and help her start cozy sundays). SF is also not perfect: some people are flaky and it obviously doesn’t have the energy of NYC, but it really has its own charm.
the fact that apartments in SF are actually spacious and pleasant to spend time in is significant. across all the apartments I lived in in NYC I never had a proper, spacious living room. this makes it harder to have casual hangouts late at night—bars (or the rare community space like Verci) end up being your only option.
if you’re in NYC and are looking for chill events to connect with others, check out midnight cafe! I helped start it and my cohost is continuing to run it. I also recommend fractal, verci, storytell, and telos haus.
and if you’re in SF and interested in joining the events I’ll host here, fill in this form.
I’ve also noticed that this isn’t just a problem of not having enough energy: I tend to give up on friendships too easily when things get uncomfortable or boring. looking back, there are a handful of friend groups that I was tangentially part of (a high school friend group, a coworker friend group), and who are still close to each other to this day, but which I never stuck with for various reasons. I do think that I’ve gotten better at identifying situations like this and not taking such friend groups for granted.
one other part of finding the stability I’m writing about here is to find a life partner. that’s a whole other rabbithole that I didn’t want to get into here but which I recognize as an important part of the picture and intend to work on.
in general I want direct feedback from my friends more, even if it hurts. I’ve had a few very difficult/painful conversations this year where a close friend shared savage feedback, and it was upsetting at first but ultimately helpful for me.
Hey Kasra, I see many young people (I’m 54) lamenting struggling with friends. A couple things I’ve observed:
-It’s harder to make friends in big cities. With so many options for things to do, meeting with you is just 1 of many options.
-Big cities tend to be more transient. Many people try NY or LA etc because they are definitely exciting places to be but they can be harsh in a variety of ways that causes people to leave.
-Age matters. In your 20s/30s many factors contribute to losing friends: job changes, going back to school, marriage, having kids. This does get better in your 40s as people’s lives stabilize again
-Give up trying to replicate what you had in high school/college dorm. Those were unusual physical proximity/frequency environments that are nearly impossible to replicate as adults
-If you find even one person you REALLY resonate with, put more effort into that person, 1 awesome friend is better than 50 acquaintances. The kind of person you call in an emergency.
-By the time they’re 50, most men do not have any close friends, take this warning seriously, it’s an absolutely miserable feeling realizing that fewer and fewer people would come to your funeral. Invest now because…
-Time spent together matters. You can have one amazing outing but if you only do that once a quarter it doesn’t feel like a friend. I’ve found 2x a month feels like the minimum. In person preferable but call if not.
-Don’t look to marriage to solve loneliness. Your spouse and later kids will become your primary relational world, but many married people are lonely too, plus your spouse can’t meet all your relational needs. You need friends outside the marriage.
I wish you the best,
Dave
Thanks for sharing your thoughts in this piece. Have enjoyed your pieces in my inbox.
FWIW, what you describe wanting 'long-term friendships and stability' is part of why I ended up leaving San Francisco. It's a very transient city. I realize the irony of leaving a transient city haha. Of the group of say 50-70 friends and acquaintances who I knew there in 2011-2013, I think roughly 2-5% of them were still there 5 years later. The ones I know who are still there had to make huge tech money and/or sell a company to be able to buy a house. I'd recommend the east bay if you're looking for somewhere less transient.
But yeah, I can totally relate to having multiple disparate groups of people who don't quite gel. Having to schedule people out for an hour hang 3 weeks ahead of time. etc. I remember reading about the term 'planshopping' in a Tim Ferriss book (who lived in SF for a long while). [Planshopping - That is, deferring committing to any one plan for an evening until you know what all your options are, and then picking the one that’s most likely to be fun/advance your career/have the most girls at it—in other words, treating people like menu options or products in a catalog.]
The East Bay is still fairly transient but people stick around a lot longer. I'm also finding it's easier in my 30s to find people who are down for long chill frequent impromptu and satisfying hangs.
I wish you the best of luck in SF.