Road Trip Part 3 - The End

I jinxed it. I said more than a few times, "I don't know where I'll end up after this trip, but definitely not San Francisco." So of course I live in San Francisco now. I'll explain how this happened.

I posted my last update a bit over a month ago from Salt Lake City. By then it was almost time to send out job applications. In a basement in Boise, I finished my interview prep curriculum. The next morning I went down the list of companies I had researched and applied to all of them. The relaxed part of the trip was over and the hectic one had begun.

From Idaho I drove out to Seattle, where I had set my heart on living. Close friends from Pittsburgh and Youngstown put me up at their apartments in Bellevue and Tacoma. I took buses into the city and got to know the menu of young people neighborhoods. I pictured my life there. Yes, I thought. I could live in a condo like that, a few blocks from the Trader Joe's. I could frequent this park with the massive trees. I could bring my dog and mingle with the other flannel-clad, dog-owning young professionals. We could exchange tips on which happy lamps to use to keep our seasonal affective disorder at bay.

From Seattle I schlepped down to San Francisco. I expected to hate it. I had visited SF only briefly before, so my impressions were shaped by the many think pieces that paint SF as a tech-driven dystopia.

With my heart set against San Francisco, I still endeavored to see it with fresh eyes as I had with all the cities on my trip. If I gave Cincinnati the chance to exceed my expectations, why not San Francisco? And sure enough, there is a lot to like about this town. There are hills with views of the Pacific, the Bay, and rows of gorgeous Victorians. The weather is pretty much ideal for me - not too hot or sunny, plus no snowy or rainy season. The biggest draw is the houses packed with ambitious, curious young people. I remember starting my road trip in New York City and feeling so energized by night after night of great conversation with fascinating people. San Francisco feels the same way, but while in NYC everyone had a podcast, in SF everyone had a deep learning side project. It's absurd and I can't help but love it.

On my second day in town, I had an onsite interview with Sourceress. I had avoided applying anywhere in San Francisco, but I happened to be acquainted with one of the cofounders and they seemed interesting. When I came in for my interview, the four SF-based members of the company were still operating out of a spare room in the cofounders' apartment. (Since then they have moved into separate office space by renting out the apartment upstairs.) Talking to every member of the team, I quickly concluded that they were all crazy smart. And looking at what they had built in a short time, it was also clear that they worked crazy hard. The whole environment was intoxicating. I had only ever read about places like this, and here it was in front of my eyes. A short time later I had an offer.

I started to fear how smitten I was with Sourceress. I had already taken a pretty big risk by leaving my stable life in Chicago and ventured out into the unknown. Was I really about to roll the dice at a startup? Meanwhile, responsible options were turning up in Seattle. After spending a few more days exploring San Francisco and the East Bay, I had to drive back up to Seattle for a round of two onsite interviews there. I emerged with two strong offers on good teams at Microsoft and Axon. A job at a well-established, publicly traded company was precisely what I was looking for when I started my search. Now I had two in front of me.

I agonized over the decision for days. I threw away half-full bowls of cereal because I was too nervous to eat. As I assume all Seattleites do when making pivotal life decisions, I stood on rainy beaches and stared at the water. I made 12 pages of pro & con lists. To their great credit, the Sourceress founders patiently addressed all of my cons and respectfully yet insistently kept making the case to join them.

My pro & con lists and seaside reveries kept leading me to Sourceress. They had made me a strong offer, I would get to dive deeper into ML and data engineering, and - most importantly - they would push me the hardest in both engineering and people skills. But I kept recoiling from that conclusion. I worried I was unduly infatuated with the hip, young company and and undervaluing the older, better-established ones. Phone calls with my closest friends helped push me over the edge. I trust the people closest to me to know if I'm not thinking like my usual self. Once my friends not only confirmed my thinking but also started listing off arguments that were word-for-word the same as the founders' arguments, I was sold. I started driving back to San Francisco the next morning.

The last two weeks have been a euphoric, anxious blur. Within a few days I had signed my papers at Sourceress, sold my car, and found a place to live. I still wake up every morning in a mild panic. "Oh my God. I'm really doing this, aren't I?" Then the panic subsides and I start my day in the California light.