Reflections On Living in San Francisco

This city always did shake you awake. As a teenager, I’d fall asleep on our family’s drive to San Francisco. The rhythmic thudding of our tires over the rickety bay bridge would jolt my eyes open to a sea of skyscrapers enveloping us as we entered the city.

San Francisco has always been a thread weaved throughout my family’s history. My parents protested the forced evictions in the I-Hotel in 1977. I’d rap Forgot About Dre lyrics on field trips to the Exploratorium. I remember staying at the Nob Hill Inn, on Pine & Taylor. We’d climb Taylor street’s steep steps and it made me feel like SF was a city where you could easily fall over. Driving through the city was terrifying, and I’d hold my breath, hoping our car was powerful enough to climb up California Street. In Japantown, we’d run through the aisles at Kinokuniya bookstore after slurping down handmade udon noodles from the woman with powdery hands.

Through the eyes of my childhood, San Francisco was a place of wonder and new adventures. San Francisco was the catalyst of my love for big cities.

When I first moved to the city, I lived in an in-law on 42nd and Ulloa. It was my aunt’s place and she offered it to me for free. Daily, I’d make the hour-long work commute to Mountain View, work for 12 hours, and then drive back to SF. I’d reach the misty outer sunset late at night, often exhausted. My bedtime ritual would be to blow my air mattress as full as possible in order to fall asleep before all the air escaped from the invisible hole I could never find.

Whereas Los Angeles nurtured me into adulthood, SF challenged me to discover who I truly was. It’s hard to live in the city without feeling challenged. While it’s a city of risk takers, it’s also a city of failures. People take leaps of faith here. Few people make it across the chasm. Many come crashing down. You can see their shattered dreams twinkling on the sidewalks all over the city.

But, where else can you make your dreams come true. The bay area has birthed global change several times over. People who live here get an early beta test of what the future looks like. Companies like SpaceX, Uber, LinkedIn, Facebook, Google all operate out of here. In 10 years, the names that are changing the world will likely be different, but I’m willing to bet that they come from the bay.

Dolores Park on a sunny day

Interestingly, in a place that prides itself on it’s ambition, my time in SF has tempered mine. I observed daily reminders of the toll that ambition takes. I see the strain it places on relationships and how lonely it can get. Living in the world of startups, I know that SF can be a city that grinds you down. I know many that are exhausted by the heavy burden they’ve placed on themselves, tired of the risks they’ve taken to taste greatness. The fog in SF makes it hard to see when you’re flying too close to the sun.

Recently, I’ve seen an attempt to swing the pendulum the other way as companies, VC’s, and the startup ecosystem start to promote the merits of balance. But sometimes I feel as though that’s not SF’s natural state. There’s a collective largeness of people’s dreams that lays on the city like a heavy fog. SF is bursting at it’s seams, which led to a huge housing problem, making it one of the most expensive cities to live in the world, and causing a huge population of natives out of the city or onto the streets.

Sometimes’ the grandness of people’s dreams make them forget to help take care of the city in which they live. In SF, it’s too easy to ignore these issues. In the very heart of the city lies the Tenderloin, a smattering of hotels turned run-down SRO’s. It seems as though people would rather Uber around it then face the reality of the society they live.

And still, the pendulum swings. In the birthplace of innovation, there’s a growing movement to use technology and the lessons of hypergrowth to affect local change. That’s the thing about SF — as imperfect as it is, it knows how to iterate.

I think I’ll miss the people the most. Most of the people I know came to SF looking for something. Looking for themselves. Looking to start something. Wanting someplace to feed their ambition. The scope of people’s ambitious is as diverse as the city. I’ve formed extremely close friendships with people here because it attracts the curious, the ambitious, no matter what the goal.

I don’t think I’ll ever be ready to leave a city. I tend to fall too deeply in love with its beauty and flaws. But, when I turned 30, I knew I was ready for a more dramatic change. How cliché, for the coming of your third decade to be such a stark reminder of your mortality, and a kick in the butt to get going on all your life plans. When I first realized that I might have the opportunity to move to Portland, I felt something slowly squeeze around my chest. Half fear, half excitement, I knew that Portland would be a new adventure, a new stage of life.

In Portland, I trade fog for rain. I trade skyscrapers for greenery. I look at Portland not with the uncontrollable excitement of a child, but with measured excitement that this place could be perfect for what I need in this next phase of my life.


I’m thinking of writing more…aiming for once a month. Hit that ❤ or share if you liked this and to give me the kick in the butt to write the next thing.