One year at Stripe
November 07, 2019
I joined Stripe over a full year ago. It was my first foray into full-time employment, which meant that there were many ways to stumble and many things to learn. To mark the occasion, I wanted to reflect on those things, as well as share them with the new class of new grad engineers (hello!). And just a caveat: this is not any sort of definitive guide, just my own experience. In the words of Mary Schmich:
If I could offer you only one tip for the future, sunscreen would be it. The long-term benefits of sunscreen have been proved by scientists, whereas the rest of my advice has no basis more reliable than my own meandering experience.
Also, these are things that I am by no means perfect at! I am still working on all of it. So without further ado, here is an unsolicited, wordy, and non-exhaustive list of what I’ve been learning in my first year at Stripe:
Asking better questions
I’m not the best at asking for help. I err on the side of struggling on my own much longer than I’d like— something I realize as it’s happening, but especially in retrospect. In addition to that, Stripe has a lot of documentation to navigate: we have a plethora of information and internal docs, both up to date and not. As a result, getting unblocked was challenging at times. I could spend way too long stuck on certain tasks, going down rabbit holes only to emerge sheepishly for help.
What’s helped me in making progress are documenting my thoughts and asking good questions. Julia Evans has a fantastic blog post about this! Some things that I find to be helpful:
- Framing my questions in the context of “what are you really trying to do?” This can often save the answerer a lot of time and get me the answer I actually need.
- Stating what I already know. I try to explain what I’ve tried and where I’m coming from. The act of doing so helps me reason through my understanding better, and helps uncover the gaps in my knowledge.
- Using existing public forums (e.g. Slack channels, JIRA) over private forums or DMs when possible. This allows for shared information and captured state.
- Just being okay with asking questions that I might think are silly. Especially in conversations, asking for clarifications when I don’t know something is crucial for making it a productive one.
Keeping a record of my work
In my first performance review, I scrambled to look through all my old PRs and docs and calendar events — we have reviews every half, and I definitely could not remember everything I did in January by the time June rolled around. I don’t think I completed all my reviews until the morning of July 4th (the day of the deadline), right before leaving for a trip. 😬
Now, I capture all of my work in a centralized doc. It’s a simple Paper doc that is for my eyes only, where I have a list of prioritized to-dos that I review daily. It’s also a dumping ground where I document things I’m learning and doing in real time. If I’m stuck on something, I have a record of what I’ve tried or ways I’m thinking about it. I also use it to reflect on past work: it’s fun to scroll through and see what I was thinking, what was challenging, and what I actually did.
Every few weeks, I use this doc to add to my brag doc, a concept I learned at Stripe. Brag docs helped me reflect on the half (what went well / not so well? how have I grown? what did I really love doing and how can I do more of it?), and to make sure that my work was not forgotten. In the last performance cycle, it was especially useful since I got a new manager halfway through— so I shared it with him and peer reviewers to use as a reference point for their reviews. (And whenever someone shares theirs with me, I am very grateful.)
Being vulnerable about how I’m doing
I often found it hard to be open about how I was doing, particularly when things got more challenging. I felt the need to reassure my manager and team that I was doing fine, just as everyone else around me seemingly was too.
But doing that was not nearly as effective (and relieving) as being very honest with them, especially if I was struggling. If I was having a bad week for whatever reason, I’d make it a point to share what was going on in my 1:1s. I realize how especially important it is (at least for me) to have a manager and team who allows me to feel that level of openness. It’s also great to have close friends and communities at Stripe that I could share a safe space with, even outside of my team. Confronting challenges together meant that we’d build a mutual level of trust, and I’d grow much more with them than struggling alone.
Being proactive about my growth with regular check-ins
I didn’t receive my first performance review until a couple months ago, which was a full 11 months into my time at Stripe. I realized this would be the case a few weeks after I had started in September, and felt a bit nervous— what if I didn’t know I was doing poorly until then? Luckily, I was able to get a lot of helpful feedback in those 11 months that helped me learn and grow.
Some practices that helped:
- Checking in with my manager about expectations for my role. Once every few months, I’d chat with them about how I was fitting with Stripe’s expectations for my level, and we identified areas to focus on together. In 1:1s, we would try to check in on my progress on those areas.
- Setting up regular (~biweekly) 1:1s with teammates I worked with. It was a great way to hang with them and get to know them personally, as well as to have a dedicated time where we could check in about our work together, and give and receive feedback.
- Working with my manager to get more formal written feedback after I’d been at Stripe for about 6 months.
- Learning how to give and receive feedback better. I took our feedback workshop (facilitated by Stripe’s Education team), which was helpful! I especially like the nonviolent communication framework.
Learning how to manage energy, motivation, and focus
In an ideal world, I’d be super productive all the time and highly effective at getting things done exactly when I want to. But I have needs, whims, desires, distractions. Sometimes I’m a bit sleep-deprived, or stressed, or feel completely unmotivated, or am incapable of focusing. I’m not a robot, even though I have an occasional tendency to set unrealistic expectations as if I were.
What I’ve learned is that it’s ok to not meet those expectations. Instead, my responsibility is more to develop an awareness of what makes me tick, and strive to create the best environments for myself. I’ve learned that:
- I have the most energy on a solid 8 hours of sleep, after running through Golden Gate Park in the morning. Some tea in the morning and a break in the afternoon keep me going.
- I’m most motivated and excited when I encounter a good-sized challenge, after great conversations / pairing sessions, or when I feel ownership over something.
- Large chunks of time help me get into a deeper focus mode, so I try to block out my calendar for that every week.
- When I’m most stressed or anxious, I tend to try to wake up super early and get less sleep. This never really works out well! It’s usually better to take a full night’s sleep.
These nuggets of insight about myself might evolve, but they serve as helpful guides in structuring or approaching work. I find it helpful to share them with my manager as well, so we can check in about them occasionally.
Feeling less afraid to take ownership
For me, taking ownership means caring a lot about Stripe’s work, impact, and users, and pushing for ways to make things better. My first manager really encouraged this. In our first 1:1, I eagerly asked for advice on how to do my job well. One of the things that he said was to identify areas that need attention and own them. I was a bit skeptical— how could I possibly do that while knowing so little?
But he— and many others— gave me the space and encouragement to try it out. I brought up issues that I saw (e.g. in product or process) and ran with them. Sometimes I faltered and needed a lot more help, but other times things actually worked out okay, even well! I realized that a fresh pair of eyes on a team or project is often valuable, and that maybe I had underestimated my ability. These experiences built up my confidence and pushed me to grow a lot, which also made work much more fun.
Finding ways to align values + interests with the job
Here’s a question I’ve wondered a lot: what makes someone love what they do? It’s certainly different for everyone, but the answer has become a bit clearer for myself. In addition to working with wonderful people, I’ve realized that having strong alignment between my values + interests and what I do is a crucial piece of the puzzle. At Stripe, I feel pretty lucky to be able to find plenty of ways to do that. And it makes a huge difference.
A few examples:
- I really care about empowering others → I had an intern this past summer and it was one of my favorite experiences.
- I value intentionality and reflection → I helped formalize my team’s sprint process and run retros, which required a lot of that. And I write things like this.
- I care about engaging with my local community in SF, and issues we’re facing here → I got involved with our SF community engagement team, partnering with local nonprofits.
As I’m gaining more experience, I’ll get to learn more about what makes me excited, which in turn helps me identify things I’d want to work on.
Cultivating work-life balance
As a new grad who just moved to a new city, I definitely felt the pull and had the ability to put in long hours. (The great food at the office doesn’t hurt either!) I felt like I had a lot to learn and prove. Fortunately for me, the teams I’ve been on actually cared a lot about work-life balance.
So instead of working more, in the past year I’ve also done some other things too. I learned to play a bit of guitar, read a bunch of books, wrote poetry and essays, cultivated my community, learned some Spanish, volunteered, and got out in nature as much as possible. And I did these things for the pure enjoyment of them, instead of attaching any sort of ambition or expectation.
Having a full life outside of work has helped me come to work feeling energized and whole. I’m super grateful for being encouraged to foster this balance, and plan on continuing to establish those boundaries.
Finally, I’ve been surrounded by wonderful mentors and peers who’ve supported me throughout, and made me see how much better it is to not go about it alone. Be it anxieties or tears, celebrations or exciting milestones, their generosity and presence have made my time at Stripe particularly great. Onwards!