Why I’m leaving San Francisco

I am about to become one of the 20 somethings leaving six figure paying jobs to live their “best life” traveling abroad. I cringe at the thought of being judged as “basic.”

already lived my best life here tyvm

There are many reasons people quit jobs, leave existing lifestyles, and choose to pursue something completely different and unfamiliar. I want to state first and foremost that I am not taking a gap year or time off.

We are often waiting for life to start after a certain milestone or event; such as waiting to graduate to start going out to network, waiting to get on a more regular work schedule to start going to the gym, waiting for after a holiday to start reading, but when looking back, I realized that was just life passing by as I was waiting.

Leaving San Francisco is not a break from my life, but a part of my life going forward. I don’t want to come back unchanged, as if I never made these decisions. I hope to continue to contribute to society, read, go to the gym, hike, pursue other hobbies etc, the same way I would have here.

Maybe I’ll find an exciting opportunity in Asia and decide to stay. Maybe I’ll start my own business and go where it takes me. Maybe I’ll decide I want to come back to work at tech companies in San Francisco. Maybe I’ll keep wandering. All these options and more are completely valid in my mind.

So why am I leaving? It was not an easy decision. Let’s start with what I’m leaving behind (in no particular order)

  • Friends ❤
  • A beautiful 1100 sq ft dream apartment + the 5.5k sunk cost to back out of my lease + never being able to rent there again because the landlord hates me now
  • A people manager position at Wish + unvested equity
  • Offers from Facebook and 2 start-ups with xx% pay raises
  • The benefit of being engulfed in the latest ideas, trends, technologies, and optimized operations so there’s no need to put effort in “keeping up”
  • The easy access to opportunities and people building crazy products and business that scale and change the world
  • The only adult life I have ever known where every part of it was fully my choice
  • The opportunity cost of everything if I come back having accomplished very little

I love the life I have built in San Francisco. I believe that if I stayed here and continue down this path I would lead a very happy, even fulfilling life.

At the time of moving to SF in September 2015, I shared a journal entry from September 2014:

“As people share what Facebook shows of what happened on this day years ago, I’m going to share a line I wrote in my journal before I boarded my flight to California on September 15, 2014. ‘I am so afraid of being alone with the unfamiliar, but I am more afraid of being stagnant. Terrified that If I stay in one place for too long that that will be all there is for me.’
I found comfort in a clear direction I wanted to head and failure to me was not an option.”

The terror of a certain life drives me still. I can see a clear path in front of me: a fairly linear, positive sloping career trajectory and standard of living. But what if that’s all there is to my life? The hunger for more, even if I don’t know what that is, takes over.


So why can’t I just shake up my life here? I like lists; so here are 3 reasons (with sub reasons).

1. San Francisco is making me less ambitious

a. Because I’m not taking enough risks here

Moving to San Francisco after graduating was the best decision I could make as a step towards my goals of working in tech and being a start-up founder.

Looking back today, I realized that no matter which role took (data, operations, sales) and which company I joined, I would have the same opportunities available to me today. No matter where I went, with 3 years of experience, I would likely have the same choices in front of me: be at a mid-level/manager position, a mid-level individual contributor role at Facebook, and a range of flexible titles at different start-ups. I would still have the option to quit and leave SF too.

I don’t want to look back 3 years from now and think the same thing: that my choices didn’t matter at all.

b. Because of the comfort a full time job gives me

Living costs are incredibly high in San Francisco. Average rent prices for a 1BD shared apartment is ~$1500 USD. My credit card bill averages $2000USD/month on top of rent.

c. Because I literally cannot work a side hustle or quit my job without leaving the country

I am Canadian and the TN visa (and most jobs) have clauses that do not let you be employed by any other employer (including self employment). Although this is a solvable problem, I can find a US business partner, get a VC investor to sponsor a visa, or go under the table, there’s no clear route.

d. Because my friends who stayed in Canada are more entrepreneurial than my friends here.

I see old classmates leaving corporate jobs to pursue their own ventures. I moved to San Francisco to train myself for the day I could be self-employed, yet those who stayed in Toronto are becoming entrepreneurs and launching ambitious projects at a higher rate than my entire network in SF.

e. Because San Francisco is very homogenous

Everyone is doing the same thing. From working the same jobs to thinking about the same problems. If I ever hope to find a passionate cause that I want to dedicate myself to, I need some outside inspiration outside of only interacting with people who live and breathe blockchain, self-driving cars, fundraising rounds, and CTRs.

f. Because I like going 100% all in, no plan B

I really don’t have the headspace if I’m working a demanding tech job.


I know that I can work through all these problems. I can be more frugal, more resourceful, and put more effort into networking in different industries; but these downsides are also what makes San Francisco so great. This is the best place to pursue a tech career, to meet likeminded, brilliant people, and to have an abundance of fun things to spend a paycheck on.

2. I want to find out who I am, without my identity tied to the life I had built here.

Every time I travel I come back with a bit more understanding of who I am. When abroad I don’t have my entire identity here in SF. Who am I without introducing what I do for a living, where I live, who my friends are, my hobbies and interests here?

How exciting it is to start anew and find out who I will become once I leave. Who will come into my life? Where will I spend my time? How will I support myself? What new skills will I learn?

3. There’s a world out of the bubble and I have a strong enough foundation in San Francisco to come back

I am confident that my network and work experience are strong enough to come back to San Francisco get back on my current life track — sans recession.

I joked that I haven’t done anything that isn’t irreversible yet after I made the decision to leave. There were days before backing out of the lease, before giving resignation notice at Wish, before getting rid of all my furniture.

But when will this decision ever be irreversible? I can get a new lease, I can buy new clothes and furniture, and I can find another job here.

There’s more out there, I’d like to go experience it too.

4. I’m taking enough with me

Here’s what I’m taking:

  1. A 40L backpack of belongings
  2. My boyfriend with his own independent goals
  3. $10,000 budgeted funds that I hope I won’t even touch
  4. One or two remote, part-time consulting contracts
  5. Me and my confidence that I can figure out a way to be productive and contribute to the world while sustaining myself

What could go wrong?


What I’ll be doing after I leave is thoughts in progress! — So are some fun projects to document this beginning of Chapter 2 of my life! (I consider SF Chapter 1 and anything before graduating the prequel)