What I Miss About Working at Stripe
Nostalgia for another way of working
Hello, Every readers!
When writer and researcher Brie Wolfson thinks back on her time working at Stripe, the thing that stands out to her is that people really cared about the work. Cared enough to do multiple passes on a piece of copy that wasn't working, or pull long nights sprinting toward a launch. Cared so much that they knew pieces of company documentation by heart, and that nobody wanted to be the first person to leave the office, even on Friday.
It's the kind of culture that Silicon Valley was once known for—a culture that, Brie argues, seems to have fallen by the wayside. There are reasons for that, of course—the current state of the world is making it challenging to give 110% to anything, let alone work. But Brie can't help feeling that something vital is being lost: a way of working that is, yes, extremely challenging—but also deeply meaningful for everyone involved.
Enjoyed this piece? Pair it with Sam Gerstenzang's Operating Well: What I Learned at Stripe for another perspective.
In my first five years out of college, I worked at five different companies. The allure of Silicon Valley pulled me in, but after a handful of pretty meh jobs, I was starting to wonder what all the fuss was about.
Then, in 2015, I joined a random little payments startup in San Francisco called Stripe where things felt different.
The office was pretty quiet—people were cranking. Conference room whiteboards looked like something you’d draw in a cartoon about a convoluted math proof (those, I soon learned, were the payments flows that we all eventually came to know by heart). We were encouraged to write everything down and then share it to a Google Group that anyone at the company could subscribe to and read, whether it was a meaningful strategy document, personal musings on a topic, or a mundane email exchange.
The mission of the company, they told us, was to “increase the GDP of the internet.”It was a little abstract, but we believed in it enough to recite it with pride. At meal times, people sat with whomever was around instead of pinging their cliques. Everyone stayed for dinner every night—in part because there was work to do, in part because chef Tony was cooking up something delicious, but mostly because there was no way I was going home before my neighbor was. Conversations often found their way to a whitepaper or book someone had recently read or posted in our inspiration Slack channel (I was surprised to learn that talking about the latest novel I was reading seemed as interesting as the whitepapers, even to the engineers).
When writing emails to customers, we were told not to use phrases like “thank you for your patience” (too presumptuous) or “as mentioned earlier” (passive aggressive). Sending meeting notes was a privilege, not a chore (documentation for the win). My colleagues chimed in on my work—because I asked them to, and because it made the work better, not because they didn’t trust me. Once, the CFO called me after sending out notes from a “postmortem” I ran to remind me that we should use the word “retrospective” instead (it’s more reflective of what we were doing and a lot less morbid). My work was meticulously but warmly critiqued by my peers and leaders alike, and my work got better and better because of it. You couldn’t get through a single day without hearing the operating principles cited multiple times in the run of work. Employees could recite content from iconic company documents verbatim —sometimes years after they were originally published.
I’d heard the trope that company culture was up to everyone to build, but here we were actually doing it. Stripe was a Big Mood and we were all all in. On all of it.
It felt like magic, but there was deep thought, care, and intention behind everything. I had a tingly feeling that I was part of an organization that had cracked something about creating a great culture. Over my subsequent half-decade working at Stripe, the company 10x’ed in size and the impact of the relentless focus on doing great work together, and being stewards of company culture, revealed itself over and over again. My work kept getting better. My relationships with colleagues kept getting deeper. The benefits of becoming a better collaborator and communicator extended to my non-work life, too.
Inspired by what was happening for Stripe as a company, and for me as an employee and person, I started diligently taking notes on the things we were doing to build the company together. I became obsessed with reading and talking about how company cultures come to life (somehow my dinner invitations are waning…). I also raised my hand to play a role in many of Stripe’s culture-shaping initiatives:integrating newly-acquired teams, drafting our first inclusion principles, standing up a company-wide planning process, interviewing candidates including prospective company leaders on their cultural fit, and creating a forum for Stripes to share their personal histories with each other. It all deepened my connection to my work and colleagues.
In 2018, my curiosity about culture-building turned outwards when I began working on Stripe Press, Stripe’s book publishing arm dedicated to advancing ideas for progress. I talked to readers and writers, most of whom were contemplating how to bring people together to do great things, whether within the walls of a company or in society more broadly. I studied how ambitious organizations known for having strong cultures built theirs (think: Apple, Amazon, San Francisco 49’ers, DARPA, Bell Labs). I devoured hundreds of books, podcasts, and essays on the topic. Then, I started writing my own stuff on the topic and helping companies implement the tactics I advocate for.
After all that reading and talking, I can say with confidence that nothing great in this town is built without the whole team linking arms to build it together. And, that true collaboration makes the whole greater than the sum of the parts. And, that getting there requires working your butt off to do work you’re proud of and leaning on and supporting your colleagues to do the same. At Stripe, we had all that pulsing through our veins.
There’s no way around it:the culture was demanding. I spent many late nights working. I cried more than a few times after feeling like I let a user or a colleague down. My heart would beat out of my chest before heading into an exec review. There were many times that I had to grab a colleague for a calm-down lap around the office after we decided to yet again delay the launch I was sprinting towards to get that final pixel perfect. My imposter syndrome was through the roof. Once, my manager asked me to reconsider the vacation I had been planning because my team needed me. “If you go, who will cover your work?” I looked around at my colleagues who were also regularly working 15-hour days and decided to stay put. I’m proud of that choice. Call me masochistic, but I have to admit that it felt good to care about anything that much. And, to be around people who I know cared that much too.
Once a candidate asked me what my favorite period in Stripe’s history was. I thought for a second. “This may be weird, but it was in 2015 when our API was facing major stability issues.” She raised an eyebrow. I started squirming. “You look surprised,” I continued, trying to regain some composure–I was selling her as much as she was selling me. “It’s just that we learned so much about how badly our users needed us and everyone really stuck by each other and made themselves available to help in some really spectacular ways.” I prepared to tell a story about how the sales team ordered a bunch of pizzas to the office for the account management and support team, when they realized we were going to be in for another late night. But she jumped back in. “I guess I am surprised. But it’s mostly because you’re the third person to mention that same thing to me today.”
Lately, I can’t help but feel like Silicon Valley has lost this culture. I don’t hear people talking about work this way anymore. Maybe that’s for the best. Maybe it isn’t.
The shift towards remote and hybrid work isn’t doing us any favors in the collaboration department. Coordination overhead is through the roof and colleagues are now literally and figuratively further away from one another. I know there isn’t a single person on this planet that hasn’t been deeply and existentially affected by the crushing weight of the relentless stream of dismal global events over these last few years.
I won’t speak for anyone else, but I will say that this is the first time in my life that I’m not so confident the future’s going to be as rosy as I once was. The reasons work life might not be number one on the priority list right now are not lost on me. But I am still nostalgic for a time when the gravitational pull of work was strong. For me and everyone around me.
I suppose it’s not so much that I miss working at Stripe (and I am sure it’s a largely different company than the one I left more than 3 years ago now). It’s more about missing that universal agreement that it’s really, really cool to devote yourself fully to your work. And to expect that from your colleagues in a way that makes you feel that “we’re all really, really, really in this together” kind of way.
I have encountered many people who talk, write, and tweet about that kind of all-consuming culture from a place of dissatisfaction, mistrust, skepticism, exhaustion, and restlessness. I know some people are working hard. I know others aren’t. I know people aren’t feeling seen or recognized or like they’re doing work that matters. Maybe you’re one of them. I get it. I feel that way too sometimes. And I don’t think people should cry or feel like impostors or skip their vacations regularly.
But I do think work can be a source of real meaning in life. But, we’ll only ever get out what we put in. And in the case of work life, it is kind of a collective decision. Once your neighbor starts signing off Slack at 3:30 consistently, it’s hard not to do the same. If your closest collaborators don’t turn stuff around quickly, why would you? If there’s no one in the room agitating for doing that extra copy pass to punch up that blog post, why not just ship the meh version and use the extra time for a jog or a drink with friends? The path of least resistance is right in front of us, and we are taking it.
I’m all for creating healthy boundaries that keep us satisfied and emotionally healthy—inside and outside of work. And of course I believe you can love something without it having to hurt. But I’ve never truly loved anything that didn’t move me to my core. I can’t help but wonder if all this effort we’re putting into keeping work at arm’s length is actually holding us back from being our best selves.
Because what I’ve learned from having the privilege of working in a place that asks for my best and helps me get there is how much it can unlock in a life. The benefits extend far beyond the skills required to get great work done. The really, really good stuff comes from looking back on something you created and thinking, “I had no idea I could do that.” It comes from looking around and thinking “wow these people helped me, really helped me, get there.” It comes from looking inside and seeing how deep and enduring those feelings of pride, satisfaction, and gratitude really are. And what happens when you have so much it gets to spill over to the other aspects of and people in your life.
A few months ago, someone complained to me that the new (very hot stuff) startup they were at had a “lgtm culture.” Upon inquiry, they explained that no matter what they do or how good it is, everyone just says “looks good to me.” “I know I should feel good about being a competent, trusted, contributing team member,” he continued, “and my new colleagues are so, so kind, but at the end of the day I just feel like no one has any standards.” He looked down at his coffee for a moment. “I’m afraid I’m never going to see my best work again.”
Yikes. Now multiply that same phenomenon across every other person working and every other company. What is that going to do for our collective impact? What will that do to progress? Mega yikes.
I’m not exactly sure how we balance the realities of the world today with a working life that asks so much of us. But I do know leaning all the way out isn’t the answer. I hope we find the right way through it, together. We certainly need the support of our leaders to get there, but I know from experience that anyone, in any corner of an organization, can play a meaningful role in building the organizations we want to be in.
And when we do, I think we’ve got a shot at transforming organizations into the incredible sources of community and self-actualization they should be.
Believe me, it’s possible. And believe me, it’s as good as you imagine it could be.
Brie Wolfson researches and writes about the ways great organizations coordinate and helps founders build more cohesive teams. Before that, she worked at Stripe (BizOps, Stripe Press) and Figma (Figma for Education).