What I Miss About Working at Stripe

Nostalgia for another way of working

Marvin Meyer | Unsplash

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 fora culture that, Brie argues, seems to have fallen by the wayside. There are reasons for that, of coursethe 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 challengingbut 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).

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@adventuring-sloth almost 2 years ago

The culture stopped because the equity-sharing culture of Silicon Valley leaders stopped. It used to be that equity was a very large part of a compensation package, partly because startups didn't have cash, but mostly to incentivize employees to work hard to achieve the company's success, knowing they'd share in that success.

Employees would be given very generous equity packages and as a result, many of the bottom line employees from the early days of the .com boom hit it big, with 6 or 7 figure payouts when the company was bought out or hit unicorn status. So they were highly motivated to work those 15+ hour days.

But the equity culture has changed for two reasons. The first is that the cash flow has significantly increased in the valley. After the first generation of millionaires and billionaires started up VC firms to find more unicorns, they began pumping their wealth into their investments. No longer strapped for cash, startups could afford to pay salary instead of equity.

However, this isn't the main problem, as there's nothing stopping a company from paying salary *and* equity. The real problem is that every founder in the valley now has dreams of being the next Jobs, the next Zuck, the next Bezos. Equity is hoarded for the founder, cofounders, and maybe a tiny handful of first gen employees. When I first moved to SV about 8 years ago, the first startup I worked at offered 15000 options vesting over two years. That's already a significant decline from the hay-day of high equity startups. My most recent startup offered me 5000 options vesting over several years. The next one will probably offer 1000 options over 10 years.

Usually when you bring this up to a modern valley CEO, they'll say something along the lines of "you should care more about the mission than about getting rich", which is a horrible attitude to have to attempt to gaslight your employees. They *do* care about the mission or they wouldn't have taken the job. There's still high demand for tech workers out here, none of us are desperate to just take whatever comes our way. We're able to be picky. If we chose your company, we want to be there.

The fact is that humans aren't one dimensional. We care about multiple missions. The mission of the company, sure. But also the mission of raising our kids. The mission of the volunteer causes we're involved in. The mission of other companies we've invested in. It's about work-life balance. At the end of the day, I care about work but I also care about life. If you want me to tip the scale towards work, you have to offer something more than just a noble mission. My life is full of noble missions.

Plus one hand washes the other. If you do take good care of me, that will come back to you, not just because I'll pull the extra hours, but because I'll be able to do so at lower stress levels. I'll be able to afford extra childcare so I don't have to worry that staying late at work means no one is watching my kid. I'll be able to pitch in on the weekend knowing my spouse is able to relax because we have enough to live off one income or that the house got paid off by a big equity payout.

For some reason, this still needs to be said to every generation of new CEOs: happy employees are productive employees.

Let me share in the financial success of the company and I will make sure the company is successful.

Eric Britton almost 2 years ago

@adventuring-sloth This hits the nail on the directly on the head. What you are willing to do as the "owner" of a company versus an employee is very different and it should be.

@teriminute almost 2 years ago

I see nothing but red flags in this post, unfortunately. It's clear that you love to be in the office, collaborating in person, and that much of the value you get from work happens in that environment. However, commitment to a job doesn't mean 15+ hour days and being told you can't take a vacation because your team needs you. That's a backwards value system, IMO, as one's personal relationships and time away from the office are just as important as working hard.

Stripe has a very chaos-driven culture and that trickles down to everyone in the org, and convinces employees they need to work harder/longer/more in order to combat that. That is probably the real issue that needs to be addressed (it's not even a secret as everyone spouts that proudly as.

There is no value in burnout. (Even if you love the long hours and all-around work focus)

There is no value in sacrificing personal one's personal life and relationships for a company (and yes, they get sacrificed if 15-hour days are the norm). And yes, your company would replace you in a heartbeat if they needed to.

It's better for everyone, if you work hard for the time you've set aside to work hard. And then, stepping away when it's time to recharge.

Kirill So over 1 year ago

@teriminute I think I get what the author is trying to say.
Unfortunately, not all of us will experience a comradery of this level because it's a unique occurrence that mostly doesn't happen because it wasn't the right time, right place, right team and right manager.

I've experienced it once as well. It never felt that I was working. We were a team of 20 people, doing something cool, travelling the world and conquering competitors all whilst making good money and not having toxicity in a workplace. It never led to burnout but eventually the org changed, culture breaks IMO after a certain # of employees and its hard to be on the same page with the wonderful set of folks that came initially with the same vision.

Hard work and sacrifice for the company doesn't always equal burnout, its a myth of this decade. Its when it is toxic and involuntary.

Unfortunately, places like that are more rare that unicorns. I was just lucky enough to experience it at the right time before it broke too.

@hstan.bus about 2 years ago

Intense work builds connection, community, and fulfillment there's no denying that. I've been through the pre-IPO do-or-die insanity. The ship-at-all-costs, Sunday launch war rooms. It sucked, but through those experiences I made some incredible connections. These kinds of work opportunities should be available for those who want them.

But then I burned out. I wanted to be around more for my partner and kid. And friendships built on reliving shared PTSD aren't the only thing I want in my life. So I left and joined a slower-paced company.

I learned that you don't have to kill yourself 10-12 hours a day to build something cool. You can have high standards and still move at a sustainable pace. You can still meet and connect with awesome people. And you can also make room for life outside of work. Consider the connection, community, and fulfillment people attain through "a jog or a drink with friends". Doing good, impactful work and prioritizing your health and relationships are not mutually exclusive exercises.

The radical shifts in ways of working took away a convenient work community and has forced us to confront questions like: Who are we really? What do we want? What makes us happy? Many in the working world are now more fortunate than ever to be able to answer that question with more autonomy than ever before.

I think it's time to realize that while "it's really, really cool to devote yourself fully to your work" it's also really, really cool to look at work as a means to an end and build a well-rounded lifestyle, filled with other professional or personal pursuits that you can devote yourself to.

@good.epic almost 2 years ago

@hstan.bus This times 1000. This essay is advocating plutocratic dystopia.

@nick.deshpande about 2 years ago

What if you could love your work AND take your vacation? That would be cool.

josh spilker almost 2 years ago

Wow. This is impossible for anyone with a family. Also if Stripe hadn’t been successful woukd it be worth it? I dont think the equity amount was disclosed, but a healthy amount would tend towards a rosier picture.

@vivsha4385 almost 2 years ago

@joshspilker Exactly. She doesn't mention equity which is the real driver (even if she doesn't realize it). Without it, everything she talks about is pointless.

Brittany Berger almost 2 years ago

As a disabled person who was always fired from cultures like this for "not being able to keep up," it's worth remembering who was excluded and discriminated against in order to allow that culture to thrive. It's good tech has gotten even just a little bit more inclusive and flexible.

@every.to_2221 about 2 years ago

Wow, that was so messed up. I'm sorry you had to go through that. Cried more than a few times? Cancelled your vacation? Would not leave before someone else did?
Masochistic, you nailed it.

@inlikeclint almost 2 years ago

Living to work sounds like a nightmare. Pressurised into not taking PTO, pressurised into working late continuously and at scale is to the detriment of your health, your colleagues, your future colleagues and all their families.
Get a life, then get a job that allows you to live your life. On your deathbed, will you still be so fond and gooey about 2015 when you worked like a slave for some job?

This article conflates caring with prioritizing work and especially hours of work over every thing. The assertion seems to be that the only way to build great products is to block out everything in life. Then I guess by extension any parent should not aspire to contribute to building great products and only young college grads who can have dinner together every day should attempt it. I was hoping for a more thoughtful piece that digs deeper into working methods and specific things that stripes culture rewards to build great product. This unfortunate is just surface level conjecture

@abelbayre94 about 1 year ago

Damn loved this one

@matt.donahoe almost 2 years ago

I thoroughly enjoyed this. Great writing!

I've worked a little too hard and burnt out a few times, but it still feels great to work with a team that cares.

Thanks for putting that feeling to words.

ps: What's your favorite Stripe Press book?

@mveritym almost 2 years ago

I've worked on a team like this and I find it hard to untangle whether I truly miss the work we did or the bonds we forged. An intense work culture is one of the only opportunities you have post-college to make super strong friendships forged under pressure. That us-against-the-world feeling made me feel really connected in those weird early/mid-20s transition years.
I think we did genuinely inspire each other to do better work but I can't remember why we thought that particular work was so important to begin with. My sense is that many companies cultivate these intense bonded cultures to generate buy-in on work that otherwise isn't very intrinsically motivating. Once a company is more established that culture is less necessary.
Now I'm older my life is much more well-rounded and balanced but to be honest, I don't think I wanted that in my 20s. What I really craved was the sense of purpose and connection I'd always had through school and work was the only obvious outlet for that.

@good.epic almost 2 years ago

This essay perfectly illustrates one of the key pieces of the fundamental rot at the center of SV. Sure it's excellent if people are excited about their work and the work culture encourages high standards. And if there's a big crisis or a major launch there can be times when at least some folks have to put it some long days.

But if you cite everyone staying at work for dinner and the culture of it being absolutely terrible to go home before your neighbor at work as examples of the outcome of great company culture you're doing it wrong. You're part of the problem. You're advocating poisonous company culture and an oligarchic society. Your deep, physical, negative reaction to that message demonstrates only how deeply you've internalized dystopia as the end goal.

@vivsha4385 almost 2 years ago

You did the work only because you were given equity - as someone else has pointed out in the comments. Expecting people to work for a salary and caring about "oh no! My API is letting people down!" is unrealistic.

If you're earning a salary and working like this, it's time to discover your true passion and build something for yourself.

Also: The list of "great" companies this author has listed are cults. Amazon? Apple? lol!

@abelbayre94 about 1 year ago


@standstoreason about 2 years ago

Great article - reminds me of the type of people who worked with me at companies like Sun Microsystems and nVidia back in the '90s and early-aughts. Everyone seemed to care not only about what they did, and how that was perceived, many would help out others who were getting "stuck" or had issues of keeping up. Many of us would come in at 5 or 6am and stay until midnight; we also had our share of all-nighters.

Of course, back in the days of Blackberries we could stay "connected" all the time; in fact, Sun Micro was the first "virtual" company in that they had, in addition to their dozen or so campuses around SilVal, many drop-off centers where all you had to do was sign in with your "smart card" and pick up right where you left off. As the Supply Chain Director, I could be in Colorado one day and Scotland or Penang the next. Made no difference.

It was an especially heady time for me because I left "heavy manufacturing" in the NYC area to try my hand at high-tech out west. Even in the early 90's, I was an "old man" by then-SilVal standards at age 40. Learned many valuable lessons from my younger direct reports and I've always blessed the decision that I made in the early 1970's to learn about computer hardware and software and programming, even when most of my contemporaries were saying that computing wasn't going to be a thing...how wrong they were.

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