Dear San Francisco, this is a breakup letter.

Jessica Tiao
3 min readApr 14, 2023

Fifteen years ago, when I met you, I wanted more than anything to live in the city.

You could get lost in any neighborhood, walk for hours, and come home happy.

Old Victorians lined the streets. The parks. The views. The alleys of Little Italy led you to the bookshelves of City Lights Bookstore. On cold nights, you could run into a laundromat for a moment and bask in its golden hue.

Strangers would say hello or give you a warm smile. If you eavesdropped on a conversation at a cafe, they talked about the social factors of inequality and ideas on how to solve them.

As our relationship felt the years go by, things changed between us. I didn’t mind it.

I was ready for the new decade. I was ready for 2020. Mother Nature had other ideas.

Don’t go outside, they said. You will catch a deadly disease. Don’t breathe the air. But, we need you to work.

As the pandemic hit the city, the sky turned orange.

George Floyd could not breathe. He could not breathe.

Asian Americans felt the voice of hatred.

You brought the homeless, and the mentally ill to our doorstep. That’s ok, I thought, they need a warm place to sleep. How are they meant to live in a city with sky-high rent and the sheer lack of livable wages?

As the days grew longer, I was consumed by work.

Our services support the COVID-19 Messaging Alert System. Lives depend on us. The world’s communications depend on us, they said.

So we all worked.

Meetings all day, every day. Work at night. Work on the weekends.

My friends worked even longer hours.

We did what we could to bring joy to the house: we cooked food. We watched movies. We played board games.

Don’t go outside, they said.

But, I needed space. I needed space to go outside. I needed space to rest.

I packed a bag, closed the door to my apartment on 16th and Mission/Capp Street. I’ll be back in a week.

But I didn’t. I didn’t want to come back.

I went home for a break. My brother and I built a deck in the backyard. We ordered chickens off the internet. We built a chicken coop. We painted the shed.

We spent a small fortune at the local hardware store.

My mom watched as we built a sanctuary in the backyard. I tried my hand at gardening. Soil. Shovel. Gardening pots. Water. Packets of seeds. Plant cuttings.

Neighbors welcomed themselves to the backyard. It was coming to life with people, home-grown vegetables, and dogs tearing through the grass.

Meanwhile, I didn’t think about you very much, San Francisco. But, I could feel the weight.

I outgrew you. I needed a quiet place with birds chirping. I needed tree-lined streets. I wanted to hear the wind rustle through the trees. I needed sunlight. I needed clean air. I wanted to walk home in peace.

You were exhausted, San Francisco; you were burnt out. You were tired. I was tired.

We grew apart.

I could not go back to you.

I flew back up to see you one last time. I packed up my room. I hired a moving company. I said goodbye to my roommates. I found a new apartment in Oakland.

It was great while it lasted: you helped me find a career I love. You introduced me to life-long friends. I could not be more grateful.

I miss bike rides down the wiggle at golden hour.

I miss picnics at Dolores and Golden Gate Park.

I miss your cute cafes.

You are charming. You taught me how to thrive. You taught me how to think and critique society (maybe a bit too much ;) ). You showed me all the things. To you, I am grateful. Thank you.

Goodbye and all my love,

Jessica Tiao



Jessica Tiao

Sr. Product Designer @Twilio. Past lives: Crazy Egg, Kissmetrics, Tradecraft. Puppy and llama fanatic. Star-gazer. @JessicaTiao,