Leaving San Francisco (for now)

where sappy meets the reality of being 30

A few weeks before I moved out of San Francisco, I boarded a bus wrapped in an advertisement for Delve, a compliance startup known for committing fraud. Incredibly, the bus ad read: “Delve: Keeping Your CISO Out of Jail.”

By then, that kind of thing barely registered. I’d spent the last few years boarding buses with inscrutable tech advertisements, first gibberish B2B SaaS acronyms, and then for AI robots taking my job. Bus ads were just another sign of the times.

When I first moved to San Francisco, the city was still recovering from the lost years of the pandemic. Downtown was so empty you could generally cross the street without looking both ways. Vacant storefronts were so common that many building owners didn’t bother placing a “for rent” sign. Within a year of moving here, I watched entire neighborhoods return to life – bars and restaurants reopened, foot traffic resumed, matcha cafes were suddenly everywhere.

I watched AI grow from something that my friends with math PhDs were vaguely concerned about to something that my friends with marketing degrees discussed eagerly. The longtime San Franciscans surrounding me were unmoved by the transition. It’s a city of people seizing moments and zeitgeists, they told me, where people and businesses drop in for one financial cycle and out when they get the email from Meta. Everywhere I went, young people told me they were busy building a new future, and they would be here only as long as it takes.

But for a select few, life in San Francisco meant something much more. Rich with countless subcultures and thriving immigrant communities, San Francisco collects and keeps die-hards easier than anywhere else I’ve lived. I found it’s also quite easy to orient oneself around the city’s massive parks, organic-only corner stores, and dive-y wine bars as a late 20s/early 30s woman about town. Initially, I’d moved sort of ambivalently due to my boyfriend’s PhD advisor moving to Stanford, compelling us to follow. When we moved from Chicago (which I understood to be a “real city” of “real people”), I hadn’t expected to fall in love with San Francisco at all. But this changed quickly when I began meeting people.

A few months into living in San Francisco, my boyfriend and I threw an overly-large Fourth of July beach barbecue that we really had no business throwing. To our surprise, everyone we invited showed up – from a coworker I’d just met to someone I’d messaged on Twitter. I was so worried about cooking everyone a sausage that I forgot sunscreen, and I still have the sunburns on my feet to show for it. Very few people knew someone else at the party other than me, but surprisingly, people stuck around. After hot dogs on the beach concluded, the dozen or so people returned to our 550-square-foot apartment, where we made cocktails and then climbed to the top of Bernal Hill. We laid down against the brush and passed a hydroflask of whiskey from hand to hand while fireworks exploded over our heads. Essentially everyone, except for Lukas and I, met for the first time that day. Three people have since told me it was either their favorite day in San Francisco, or the day they first came to love living here.

People are unusually welcoming here, open to new ideas and new people in a way that I had not seen where I’d lived before: Southern California, Boston, and Chicago. This became a recurring theme – a man telling me something insane at a party that couldn’t be true, but listening earnestly to me when I disagreed with him.

This obsession with fresh ideas and optimization generally leads to wackiness. My boyfriend always joked about the “sauna situation” at the gym: half of the men inside talked about an absurd diet – one guy exclusively ate potatoes – and the other half of the men were inventing new ways to subvert gym etiquette. One man, wearing nothing but underwear and running shoes, said he was there to “regulate his temperature for the fifth day of his water cleanse.” There was no judgment in that sauna.

Hyper-online tech person culture surrounded me everywhere. A moderately famous Twitter guy once hit on me by claiming to occasionally text Elon Musk’s personal line; squinting at me nervously, he then asked if I was a journalist. A billionaire blocked me on Twitter after I complained about city politics. Two people, on separate occasions, looked into my eyes and told me they knew the identity of Satoshi Nakamoto; they named two different people.

I watched several friends become unexpectedly fabulously wealthy, like a piano of cash was dropped on their heads. They were so painfully unsure what to do with it that I began to have sympathy for online philosophies like effective altruism, which at least guides them somewhere.

I attended parties celebrating newfound American citizenship, the funerals of Claude models, startup funding rounds, birthdays for dogs.

And then one thing gave way to another — I embraced the frontiers of tech, never how I’d expected. While biking to a dinner party, my boyfriend was hit by a car. Some hours later, we were standing outside the hospital, his face so covered in stitches and bandages that I couldn’t make out his expression when I told him it was 2am on Halloween weekend and there were no Ubers able to take us home. It was cold and blood slowly trickled down his cheek. Reluctantly, I downloaded the Waymo app. Seven minutes later, a car drove us home.

I have stubbornly analog tendencies. I write in my leather Paper Republic journal each morning, I shoot a few rolls of 35mm film each month, and I refuse to ever own a TV. Still, the city’s influence led me to buy an Oura ring and attempt to organize my life on Notion. Even if so much of the technology I’m exposed to is just there to “hyperscale” itself, I’ve made peace with adopting what works for me.

Still, my favorite moments living in the Bay had nothing to do with technology. Nothing beats getting snowed in on a Tahoe trip with nothing to do but eat home-cooked coq au vin and gaze up from the jacuzzi to watch the snow fall onto my face. On another Halloween night, I watched a close friend direct a play inside the house of a prominent artist; it concluded with another friend wailing while crawling down its creaky staircase. I entered a state parks lottery six times to sleep inside a cabin without running water.

I camped in the woods constantly – Point Reyes four times, Angel Island twice, Slide Ranch, Potrero Redwoods, Muir Beach, Yosemite, the Sonoma coast. There’s just so much stunning nature within an hour of the city, it feels ridiculous to leave a park unexplored. On one trip, six of us friends cooked an enormous pasta dinner at a campsite above the ocean and drank eight bottles of wine. Spirits were so high that no one bothered to complain about the pouring rain the following morning – even the couple whose tent had flooded. On our way back to SF, we stopped for breakfast at a diner and wordlessly took turns drying off in the bathroom.

Eventually I found a serene beach in Point Reyes National Seashore to my liking – a perfect place to sit back against the bluffs and watch the waves crash. It’s where, to my surprise, my boyfriend asked me to marry him.

I’ll never forget the barista near my house who knew not just my name and order but to congratulate me on my engagement, because my fiancé had been telling him about it for weeks. Or the bar managers who slid me “cheeky” free drinks after I complained about a long work day, or neighbors who stopped by to watch my cat while I was away. No matter how internet-influenced San Francisco may be, the city’s raw density lends itself to a neighborhood atmosphere that, if really taken advantage of, can hardly be beat.

Sure I was constantly subjected to overheard conversation about “AI frontiers” and materially non-public information about FAANG company plans while just sitting in a coffee shop, but there’s still a lot of the city left to lean on. No other city is so obsessed with embracing the new while becoming so effortlessly a place you know by heart.

When the time came for me to move from San Francisco to Boston this June, I wasn’t immediately thrilled, but I knew it was the right decision to support my fiancé’s career in quantum computing. Like so many others my age, we moved far away to an industry hub in the midst of its own “hype cycle” (somehow, Boston is to quantum physics what SF is to AI), and we’re not sure how long we’ll be here. Still, I am comforted knowing that my job is still based in the Bay Area, and I have visits scheduled every few months. My “bicoastal elite” card is in the mail.

Still, the city is changing rapidly and I may not recognize the next iteration. IPOs are minting thousands of new local millionaires this year, and the median rent for one-bedrooms jumped to $4,000.

As the city absorbs its biggest cost-of-living jump in years, I wonder how its culture will shift with the closure of its major arts school, relentless layoffs across non-AI tech industries, and tourism that still hasn’t bounced back. Will the city’s identity grow even more closely tied to AI — or is a bust waiting around the corner, ready to seed the growth of something different in its wake? For now I’ll be sipping a Trumer at SFO, taking in the “dominating” AI billboards crowding its walls, waiting to see which way it breaks.

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* If you’re in Boston/Cambridge and want to hang out – or know someone I should hang out with – definitely email me!

Thank you to all my friends for making my last few years in San Francisco so special. I promise I’ll be back.