My Career Journey, Part 2

My journey in product

For new folks, refer to part one of this series (including more details on the motivation) here.

 During my first two product roles, I treated every project as if we were saving lives, emulating the sense of urgency that was rewarded. I learned how to take notes, facilitate meetings, and build “alignment.”  I took on extra work like organizing team socials and taking meeting notes, having no idea that this type of “housework” is unrewarded and targeted towards women. I debated every message, email, and comment, making sure that it had the right combination of content, tone, and timing. I stayed late for dinner and worked on the shuttle ride home. I learned about good and bad managers, and how mentors matter. I tried on different types of product work and found my niche as a consumer product builder. I learned how to take enough space to be taken seriously but not too much to threaten others, after a few bad experiences ruffling some feathers. I constantly felt busy, posting IG stories of my calendar, subconsciously equating my busyness with my worth, even though I didn’t know what I had actually done. I told myself I was making an impact, even though I didn’t know if that’s the impact I wanted. 

Soon, I started feeling bored. There was a part of me that wondered if the boredom was the product role or company, but it felt easier to examine the latter. So, I got a job at a startup as their third PM in New York in March 2020. It was a tough interview process, and I felt grateful to have gotten the offer. Plus, I’d get to work on a more mission driven company with direct exposure to the founder, setting me up well to eventually do my own thing. After all, it was the next step for someone with my background (and what a lot of my peers had done after their product jobs), and allowed me to flex my leadership skills while having impact at scale. While I didn’t have an idea, I was confident I’d figure it out. My dreams felt in reach. 

My first launch as a product manager!

Working at this startup was the most transformative part of my career, especially in the midst of a global pandemic. I accomplished and learned so much with some of the kindest, smartest people I’ve ever worked with. But the transition was too much, as I learned to shed big company product management for scrappy, always on startup product culture. It was difficult for me to feel grounded in my role, and the persistent chaos severely triggered my anxiety, which I started managing with medication. I was constantly reading into signals from other people, especially the founders. I was angry at myself for wanting their validation so badly, yet I also didn’t know how to stop myself from chasing it. 

The company prided itself on helping some of the most underserved people in America, and I felt proud of what we were trying to accomplish, especially during the pandemic when many of these folks were struggling. Yet this desire to help didn’t always carry over into our day-to-day product decision making, especially when it conflicted with the needs of the business. I often felt this deep seated guilt of building tech for low income people while we received shiny, fancy perks for our work. I also didn’t fully understand the historical context of the space in which we were building products, but I had little time and emotional energy outside of work to learn. I wanted to be the perfect PM, but the bar felt like it was constantly moving. Little things would constantly trigger this insecurity: not being involved in meetings that felt relevant to my work, not presenting clearly enough, not executing fast enough, not having good answers to thorny, strategic questions. I rarely felt enough, and I didn’t know if I ever would. 

I debated (again) if product was right for me. I talked to people who left product to do other things- cannabis tech, film making, acting, author- and decided that I wasn’t like them. I liked building software too much. Plus, there were things worth sticking around for: promotion, product launch, my team. But the longer I stayed, the less certain I became about whether I wanted to become a startup founder. It came with too many lifestyle, business, and leadership sacrifices that I wasn’t sure I wanted to make. But the desire to become a founder was my identity for the last five years. What else would I do? 

Stay tuned for Part 3 (hopefully the last part!)

Thing 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 Annie Duke’s book “Quit.”

I recently started Quit by Annie Duke, and it’s just as good as people say it is. She talks a lot about how people have a negative connotation associated with “quitting” (both from a language and cultural perspective), which is definitely something that I’ve experienced. Her words remind me of something one of my old personal trainers used to say: “You don’t have to overcome every challenge put in front of you. Fitness is all about optimizing yourself so you can confidently choose and overcome any physical challenge that you want.” (This applies to non-fitness challenges too). One of the biggest unlocks for me in the book was this idea around “peeking into the future” as a way to understand if you should keep going, as well as the idea that if it’s a toss up between staying vs quitting, it’s probably better to quit. Both of these seem obvious in retrospect, but her framing and examples are incredibly helpful!