My Career Journey, Part 3.
The end of my startup journey and the rise of my multi-hyphenate career aspirations
For new folks, refer to part one of this series (including more details on the motivation for this series) and part two before diving into this post.
After 1.5 years, I made the decision to quit the startup.
I didn’t wake up one day and decided to quit. It was a series of micro moments where I repeatedly questioned whether this was worth it, and consistently arrived at the same conclusion. Each time I did this exercise, I became more confident in my thought process, yet not confident enough to pull the trigger. I loved my team, mission, and product too much, so much so that I was willing to deprioritize my own wellbeing. This changed once my product launched. I hoped that the achievement would result in a slowdown of pace and change for my day to day. When nothing changed (and in some ways got worse), I handed in my notice the next week.
My original post-quitting plan was to take a sabbatical. I already had started brainstorming all the activities I was excited to explore (tennis, salsa classes, and more) as well as potential directions for my new career (MFA program? Tech policy fellowships?). This was 2021, when tech was booming due to crazy low interest rates, which meant that everyone was struggling to fill roles and hiring like crazy. All this meant some pretty interesting product opportunities came my way, including a head of product role at another Series A startup.
I loved the mission of the startup, which was very aligned with the work I was doing at my previous company. The idea of running a function was also attractive, as it felt like a culmination of where my career was naturally headed towards. Yet, I felt weary jumping into something new. Was this really what I wanted? I went back and forth in my head. Another tiny voice questioned whether I’d ever get an opportunity like this again. Like all good Asian kids, I wanted to preserve optionality, so I decided to do both by compressing my sabbatical into 3 months and starting the head of product job after.
This new role made me realize how much I didn’t want to work at startups. While I had more visibility into the inner workings of a growing startup, I also felt worse about not being able to do anything about it. I underestimated the alignment between myself and the founders, which led to constant friction over the role of product, and thereby my own role. I had also underestimated the team’s maturity and the feasibility on where they were trying to go. I had difficulty building strong relationships with my coworkers, and felt even further isolated and unmotivated. I had a sinking realization that the job I thought I was signing up for and the job I was in were two completely different things.
For a while, I blamed myself for how I felt. When I first decided to take the job, I told another former product executive of my decision. He strongly advised against the move. “You’re either going to get fired, quit, or get layered.” I despised that he was right. I felt dumb for jumping into something so opportunistically, for not listening to him. It felt like no matter what I did, I found it difficult to be happy in my career. Perhaps I needed to adjust my relationship with my work to make room for other areas of my life, like creative writing.
Let me take a step back. I had written tons of stories as a child, but gave up that hobby in college after a particularly scarring workshop experience where I decided that I wasn’t good enough to become a writer. But in 2018, I went to Cartagena, where I took a boat ride across the island. I felt hypnotized by the sparkling blue water, and I heard something inside of me telling me that I needed to get back into writing. As soon as I got back to San Francisco, I signed up for a writing class. It felt like a whole new part of my brain was unlocked. It was also part of the reason I wanted to move to NYC: I wanted to be closer to the writing scene, surrounding myself with serious writers as my interest in the subject deepened.
In 2021, after a series of writing workshops, I decided that I wanted to deepen my writing practice. I focused on regularity and hiring a developmental editor to expedite my growth as a writer. When I eventually decided to leave Landis in 2022, one of my biggest motivators was making more space for creative writing in my life, from both a work hours and emotional energy perspective. I wanted a job that gave me the financial freedom and flexibility so that I could become more than just a product manager. The itch to become multi-hyphenate was starting, and it was a matter of figuring out how to make it a reality.
Stay tuned for the final part of my journey, which will be slightly delayed given that I’m on vacation for the next few weeks. I swear I’m almost done with this series 😅
Things of Note:
Recap: This section is my way of bringing attention to a thing, person, or idea that’s meaningful/related to the mission of this newsletter. This week, I want to highlight Cece Xie’s videos that I think did a spectacular job of highlighting the reality of sabbaticals.
I’m a huge fan of sabbaticals, especially as mine really helped me explore new hobbies and interests that I’d never had the chance to explore. But I do wish I had taken a real sabbatical to truly explore a new career path, rather than taking an extended break before jumping into a new job.
That’s where Cece’s video comes in. She does a great job of sharing both the good and bad parts of going on sabbatical. It’s inspiring to see how she does it, since we have similar aspirations. My biggest takeaway is that sometimes, one “component” of your blended career might need more focus, which means the other goes on the backburner. For Cece, it required focusing her attention on her book project while law went on the side, and now, law is taking up more attention as her book project is in a better place. It’s helpful to see other models of how others are approaching a similar problem!