San Francisco, WWDC, the Summer Swift Was Born, and My First Solo Adventure
My first real solo trip as an adult: a WWDC lottery ticket from my job sent me to San Francisco the week Swift was unveiled. With the trains on strike I walked the entire city on foot, watched Bastille play, started a lifelong ice-cream tradition, and made my first, unsuccessful, run at the Pacific.
This was the trip that taught me I could do this, go somewhere, alone, as an adult, and turn it into an adventure. A lottery ticket sent me to San Francisco the week Apple introduced Swift, the trains were on strike so I walked the whole city, and I came home with a tradition I still keep and a piece of unfinished business with the Pacific Ocean.
How a kid from Missouri ended up at WWDC
Back then I was working for Suddenlink, the cable company based out of Missouri, and in 2014 a ticket to Apple’s WWDC was a lottery, you couldn’t just buy your way in. I got lucky and drew one through work, and my company stepped up and covered the conference ticket and a hotel room. Growing up we never had much extra spending money, so this was a big deal in more ways than one: it was genuinely one of the first trips I ever took as an adult, by myself.
WWDC itself was phenomenal. Sessions all day on every topic under the sun, and, of course, the keynote where Swift was introduced for the very first time, a language I’ve been avidly using ever since. I was in the room for the start of something.
The Hotel Union Square, and a tradition is born
I stayed at the Hotel Union Square, right near Market Street and the cable-car lines, a quirky, hodgepodge old place, and I loved my room. It looked out over a little parking area; when I pull it up on Google Maps now, in 2026, there’s a huge building standing in that lot, so the exact view I had either doesn’t exist anymore or has completely changed. A small thing, but it makes the trip feel even more like a moment frozen in time.
Across the street there was a Cold Stone Creamery. And here’s where a lifelong habit started: as an adult, on my own, I realized that after a long day, training, or training and walking across the whole city, I could just stroll across the street and get a scoop of ice cream. That became the tradition. To this day, any time I’m on vacation, I try to get ice cream every single night. It started right here, at a Cold Stone on Market Street.
A city on foot (because the trains quit)
That week, San Francisco’s Muni operators staged a sickout, and public transit basically collapsed. The one thing still running was BART, which is how I got in from the airport, and after that, I walked. Nearly everything I did that week, I did on foot: one BART ride and a single bus were the only times I wasn’t using my own two legs.
The first evening I walked almost the entire length of Market Street and back, then followed the Powell Street cable-car line as it climbs up toward Nob Hill. Up at the top there was a beautiful church standing in classic June fog, everything misty and gray and cinematic, and a grand old mansion up there too. I caught the sunset, wandered down into Chinatown, and eventually realized I should probably find my way back to the hotel.
The next couple of days were almost all conferences. But by June 4 I got out again and walked to a striking cathedral across the city. On June 5, I got a treat I’ll never forget: Bastille played live, back then Apple brought in bands as part of the WWDC Bash, and that year it was them.
The big day: Market Street to the Golden Gate
June 6 was the one. I walked the Embarcadero all the way, from Market Street out along the water to the Golden Gate Bridge. It was a full day of the city’s greatest hits, all strung together on foot: the piers (there was an old arcade/pinball spot out there, and the barking sea lions I first took for walruses or manatees), Alcatraz sitting out in the bay, rows of mothballed Navy ships, Fisherman’s Wharf, the little historic tall ships, and my first-ever In-N-Out Burger (honestly? just okay). Then the bridge itself, I walked out across it to the halfway point and back, before turning around and walking the whole way back to Powell and Market. No wonder this is the day my camera went into overdrive; it’s easily the most-photographed day of the trip.
Every single day followed that shape: training would let out around 4 or 5, and I’d head out for a micro-adventure, trying to see as much of the city as my feet could reach.
The one that got away (for now)
There’s one thing I didn’t manage. That single bus ride I mentioned, I took it heading west, and it was my first attempt to reach the Pacific Ocean. And I didn’t make it. I never actually got to the water. I didn’t know it at the time, but that piece of unfinished business would sit unresolved for eight more years, until a beach in Washington in 2022, where I’d finally stand in the Pacific and point across it toward Japan.
The takeaway
San Francisco gave me Swift, Bastille, a thousand steps a day, and the ice-cream-every-night tradition I still keep. But more than any of that, it gave me proof that I could set out alone and do something with it. For a kid who didn’t grow up with extra money, learning that the world was walkable, that you could just go, and look, and get a scoop on the way home, was the real souvenir. The ocean would have to wait.