The risk and reward in leaving

PM takes a break from the big tech grind

Apparently in China, nothing ever takes a break – not even funeral homes on New Year. At 5AM on the first day of 2025, three Buddhist monks chanted scripture – two sessions of 45 minutes each – as we kneeled on the ground. A hundred or so relatives poured out of shuttles that my mom rented to bring them in from all over southern Guangdong. We mourned, but my mom and uncle grieved the most. 

In the back of my mind, I had known that there was a chance I'd already seen my grandpa for the last time. Every five years, Uber lets employees take a month of paid sabbatical. I elected to spend the entirety of mine in China: the first third of the month to see David’s extended family, the middle third for David and I’s pre-moon, and the last third to see my family. My grandpa passed away on the first day of my second leg; I had been 8 days away from seeing him.

In my great fortune, this was the first time I’ve needed to confront mortality up close. When I returned to the US, the depth of sadness had passed. Coming back to corporate tech was familiar ground. On my second day back at work, I joined a meeting to rehash the same argument I thought we solved three months ago. A nauseating wave of existentialism hit me. 

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My last year at Uber

I spent five and a half years at Uber, during which I was a part of five teams. I transitioned into PM, was re-orged once, was promoted once, and switched teams twice. By the time I quit, I had quadrupled my total compensation. I worked on everything spanning platform, model-based pricing, internal tooling, and consumer/business product. Objectively, it’s been a great journey. Subjectively, I wondered if there was something wrong with me that I wanted to try something new every year. Or if there was something wrong with Uber. Or both.

Many companies tout internal mobility, but few actually live up to supporting its employees through the journey. In my experience, Uber held its promise, and to that I’m eternally grateful. 

But after five and a half years, I realized that what I was looking for either no longer exists at Uber or never will. That conclusion started congealing around summer of last year, and I let it marinate until I finally decided it was time to leave. In March, I:

• Found 3 HRBPs at Uber for an informational chat + had a conversation with an Uber HM hiring for an employee culture role

• Decided to not pursue transitioning to HR and that I wasn’t quite done with product yet

• Called/texted 6 friends to hear some thoughts on the transition, one of whom recommended that I test the realities of the startup market rather than just churning on hypotheticals

• Applied to 4 startups, 2 of which I had intro recruiter interviews with. 

• Decided that what I needed was a pause. Let the recruiters know I would love to reconnect in the future if they were still hiring

• Put in my 2-week notice

• Wrapped up everything and finished my last day on April 1st.

All of my friends expressed surprise at how quickly I moved, but it wasn’t quickly at all. I simply decided at some point that rather than sitting around and thinking about the knife in my torso, it was better to just yank and deal with the blood after.

Telling my coworkers that I was leaving opened up the floodgates. I had decided to write my bcc list manually instead of relying on a Google group. When I hit 100 people, I learned that bittersweetness is tasted on the sides of my tongue. Somewhere in my last year, buried in my exhaustion and isolation, I had forgotten how many people I worked with – and how much I liked them. I had always assumed that farewells disappeared into the bottomless well of Gmail inboxes with a 3-digit unread count (I, guiltily, have missed a few). A few folks found time on my calendar, in person or Zoom. My tech lead and a TPM partner from my first team as a PM drove up from Sunnyvale to grab a last lunch together. My manager threw me a goodbye boba party (at my request, instead of a happy hour) and my EM partner a virtual farewell with our engineers.

On my last day, I rode the elevator to the top floor of our office building and walked down, taking the staircase between each floor. I got an oat matcha three times from the building baristas. I booked my last shuttle home. At 6:02PM, while I was sitting at home on our couch, I was suddenly flooded with a torrent of Slack notifications informing me that I “have been removed from {groupname} because [I] am not in a group connected to that channel.” I put my phone down to cut some carrots for dinner. The next time I opened my Slack app, my Uber workspace was gone. I bursted into tears.

In my brief thoughts on the matter, I thought that on my last day I would feel at best exuberant, and at worst neutral. To be honest, I didn’t think much about the emotional side at all; I was consumed by my vision of leaving. Once I accomplished my goal, I was hit by the emptiness of it all. While it’s natural to grieve a romantic breakup, I can’t help but feel that grieving the loss of my workplace is a little Stockholm-esque. At the same time, this was a relationship. It demanded my time, my best cognitive output, my limited social energy, my life, dammit. 

I keep reminding myself that I had valid reasons for leaving Uber – growth made and lessons learned – and that grieving a goodbye is not the same as wanting to return. When I sweep myself up, I find that there’s many memories and people that I look back on fondly. A few Uberians (Uberians? Uberees? Fellow Uberers?) asked me for my Substack before I left – so if you’re reading this, I appreciate you.

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Money and capability

I quit my well-paid big tech job voluntarily, during one of the hardest job markets for tech workers and an unnerving political and economic shakedown. To start, I’m grateful for my financial and circumstantial situation that allowed me to do so (and to my husband, who is now an SIWTP – Single Income, Wife and Two Parrots). And second, I think it’s worth the risk.

On a macro level, I was motivated by this video on XiaoHongShu (RedNote). There’s a (somewhat readable) English CC so I recommend you just watch it, but the tl;dr is that it challenges us to think about whether we actually know how to make money. I’ve always more or less equated hireability with capability: the more capable you are, the more a company will pay you in compensation and title (and vice versa). But without the backing of their title or company infrastructure, I’ve met many white collar tech workers that are essentially hireable idiots. They’re able to perform competence, but aren’t necessarily able to “make things happen”.

I’m not trying to be judgemental in this application. I believe that economic downturn and general instability will reveal what truly “making money” means, and I’m terrified that I don’t have the skills to do so. Given what I know of myself, I’d say my fears are founded.

David’s coworker had told him (and then David in turn told me) that when young, we learn how to reach our goals in the context of our environment. In my half decade at Uber, I learned how to accomplish things “the Uber way”. Taken out of Uber, those same principles might fail, and I’d be left grasping at how to accomplish my goals, or even what my goals are. I didn’t want to go too far into my career before getting a reality check.

And I don’t want to get too far into my life, either, before deeply understanding what my life goals are. I think often of a poem I like, Lying in a Hammock at William Duffy’s Farm in Pine Island, Minnesota. I think about whether my grandpa would’ve said he achieved what he wanted out of his life. I take his age and divide it by mine. Then I usually decide to think about moving in a positive direction instead. 

That said, I have no idea where I’m going. I’m taking my ex-coworker’s advice to “get so bored that creativity hits you” (which in the last 2 weeks has meant: a lot of pole, racking up overdue notices at SFPL, and getting suckered into a game of Civ V). It feels suspiciously like being lazy. I’m trying to combat that by reintroducing agency to myself and my community, which sometimes is as simple as hosting friends at our new apartment.

After a decade of work, I suppose it’s not so bad to take a breather. Even if I get nothing else done, I’ll rest and recharge my mind. At best, I realign my career with my life. In a worst case scenario, I’ll get deported back to Canada under Trump’s increasingly erratic border control policies. Maybe I’ll finally visit eastern Canada like I’ve always wanted to. 

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Bits of gratitude

• Jamie, who inspired this section. He doesn’t know this. Hi Jamie!

• My friends who counseled me while I thought through leaving – 

  • Lisa: who advised me on faster action and feedback, 

  • Kathleen: who somehow became my therapist mid-call and set me on the right track, 

  • Derek: whose equal parts insight and empathy gave me a lot of comfort,

  • Ros: for giving me an extensive startup v. big tech breakdown as an ex-Uberian

  • Kevin: for lots of thoughts over the years on Uber + quitting, 

  • Priscilla: for giving me an unfiltered HRBP highs and lows (makes me appreciate HR a lot more)

• My pole friends and teachers. April 4th was my one year anniversary of pole!! I took up pole on a whim after feeling like I’d never get over my performance anxiety in dance. I figured that I would be forced to practice performance in pole, since it was either commit to the move or fall. Even though I started pole dancing as a “training path” for dance, I’ve really fallen in love with the art and community in its own right.

• You, for reading. If you took some time off from work, I’d like to know what you were happiest with and what you regret doing or not doing during that time.

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What I’ve been reading

Derek asked me why I chose Substack over Medium, and I had to think about my answer a bit because Medium wasn’t even a choice in my mind. Over the past year, Substack has somehow become the place I go to for fresh, diverse, and thoughtful short-to-medium-length material:

Anyways, I want to share some great articles I've read on Substack recently:

• Career

  • Liquid vs. illiquid careers

  • When to join a startup

  • Take asymmetric bets

  • How to waste your career, one comfortable year at a time

• Personal growth and writing

  • Our souls need proof of work

  • Turning off the TV in your mind

  • You have time

• Information consumption, sociology, and other

  • MAGA as master morality (really interesting take imo)

  • The death of the public intellectual

  • How to break free from dopamine culture

  • The intellectual obesity crisis

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