[2022-10-17] Basta's weekly notes

The first time I'm writing outside of work

Next Friday (October 28) will be my last day at Stripe. In 2017, I joined as a front-end engineer working on Express, a product that’s part of the Connect family, but my role sort of got mushy and ambiguous as I took on the archetypes of “The Fixer” and “The Architect” to address the needs of my team and my org. Being at least a little bit successful in that role is something I intend to write about more in the future, but a good preface for this blog/newsletter/whatever is my weekly ritual that served as its predecessor.

In June of 2020, one of the folks on an engineering team that I worked with pung me with some candid feedback. They said that they were grateful for the work that I do, but actually didn’t really know what that was. I realized that my job was not just about serving my teams’ interests, but to be a bridge to the outside organization.

That week, I typed up notes about what I did and who I met with. I gave a brief summary of all of the conversations I had. A few people read the notes, and they were well-received.

Over time, my notes got more verbose. I started leaving a reading list of documents that I’d consumed at the top of my notes: not only did this help to shine light on what I was paying attention to, it also served as a fantastic memory aid. I also started writing long-form sections about things I was thinking about. Sometimes I’d write about deeply technical concepts, and other times I’d write about team dynamics. There was no theme or structure, it was just whatever was on my mind that week.

As my notes evolved, the number of people reading them grew. Folks outside my team started reading my notes. Folks outside my org started reading them. It became a great way to have conversations with people who had similar interests or were working on similar problems.

I first realized that my notes had some amount of influence when I wrote a bit of a rant about the state of Stripe’s QA environment. I logged on the following Monday to find hundreds of people reading them. I spent a good chunk of the week responding to DMs and meeting with folks who were doing things in and around making our QA environment better.

On one hand, I can’t think of a more anxiety-inducing scenario. I frequently have nightmares where I’m still in high school or college and haven’t studied for the final exam or gone to class all semester. Just the other night, I woke up in a cold sweat because someone reminded me that by quitting my job, my credits wouldn’t transfer and I’d have to stay in school an extra semester. None of these give the same hole-in-the-pit-of-your-stomach feeling as being under the spotlight for something you’ve written down.

I think that for a lot of people, myself included, we are conditioned to not say things that we think are worth saying. When we’re young, speaking out of turn results in some kind of discipline. We associate expressing our displeasure with punishment. But what I found when I wrote my notes about QA was that a lot of folks’ ears perked up and they paid attention.

On one side, you had people who were responsible for the QA environment. I can’t imagine they’d gotten a lot of direct feedback about their area of ownership before. QA isn’t something you should hopefully have to spend many mental cycles thinking about. On the other side, you had leaders who were eager to hear about developer productivity concerns, and hearing about QA and the consequences of its problems was something that was of interest. And on yet another side were the other folks who had toiled with QA before, who felt seen.

In the many weeks since writing those notes, my manager had never told me what to write, but he did give me some feedback. First, he said that I had folks’ ears. Writing to a substantial audience meant that I needed to write accurately and with empathy towards the people who were implicated in what I was writing about. Second, he said that there was great power in being frank.

Writing accurately is something that admittedly did take practice. While I have been diligent in being truthful in my writing, truthfulness isn’t sufficient: what I believe to be the truth may not be a fact. And I have been caught out in subsequent weeks’ notes, with folks pointing out inaccuracies. Thankfully, none have been significant enough that I have a lot of regret for the error. In some ways, it feels like being a journalist: when you state something as fact, it’s important to either explicitly write that what you’re noting is what you’ve been told, or to fact check. Going through this exercise has led me to rewrite lots of weeks’ notes, after I discovered problems with my own understanding.

Writing with empathy is also something that takes practice, but I think should be easier to accomplish for most folks. If nobody ever receives critical feedback, they won’t ever make any changes. Are my wide-reaching notes the best medium to deliver that feedback? Probably not, though maybe it is if the feedback has fallen on deaf ears.

Sometimes the critical feedback isn’t directed at a specific person or team, but at an org or group. I try to make an effort to acknowledge that just because something is amiss, it didn’t end up that way because anyone is being malicious (hopefully, at least). “This is bad” reads a lot differently from “I understand why it’s this way, but the way it is has consequences which are harmful.”

And last, being frank is important. I’m not an eloquent writer, I think. And I think at least some of the effectiveness of my writing is in speaking plainly. Folks don’t want to be pandered to and they don’t want to be thought-led. My style of writing doesn’t sugar-coat concerns; it’s direct and specific. If someone else were to start writing, I’d imagine that they’d also have their own unique style, and that could be just as effective—but only if they write what they mean.

I think back frequently to my seventh grade pre-algebra teacher. She gave out extra credit for an assignment for folks to bring in posters that read “Say what you mean and mean what you say.” I don’t remember why she did this, but she hung them up around the room. In many ways, this is the core tenet of writing software: the computer needs unambiguous instructions (perhaps she was driving the same point home for algebra?). And in writing, it’s exactly the same: if you sugar-coat or dance around a topic or write without actually making a point, you won’t convince anyone. What you put down comes off as bullshit and the impactfulness of your writing goes down the drain.

I’m grateful to my manager for giving me this direction. In a lot of ways, it’s taught me to be a better writer by forcing me to think hard about what I’m writing about, who I’m writing for, and how I’m doing it. That’s been a real gift. Thanks, Connor.

In leaving Stripe, my weekly notes have come to an end, but I do want to keep writing publicly. I hope you’ll follow along. As a preface to what to expect, I really don’t want to become a LinkedIn talking head that spouts long essays about something you’ll immediately forget when you close the tab. I certainly don’t want to write anything that I wouldn’t read myself (I do, in fact, re-read everything before I hit Publish). And I’d like to think that the things I write about have a point: I might get a bit wordy at times, but I do try to have some kind of takeaway that’s more than just the title wrapped up in paragraph form.

My initial plan is to publish something every two weeks. That’ll put my next post just before I start my new job. But who knows, I might be inspired to write again sooner.

Thanks for taking the time to read, and I hope you’ll subscribe for more.