Goodbye, corporate politics (for a while, at least)

life

So, back in the early teens of this millennium, I was running a news analysis and opinion blog called Lawsonry. As the eponymous editor-in-chief, I wrote articles and featured other writers from across America, each offering introspective and thoughtful critiques of what we believed at the time was the worst that American politics could get. We published essays on education reform, prison gerrymandering, persuasive arguments about abortion law, foreign policy—if it was pulsating in the American zeitgeist, we were writing about it. But despite the richness and depth of our work, the bitter truth was that our operating model wasn’t sustainable.

We were working ourselves to death1 and not making any money. Every week, we ended our meetings by putting off the launch of our Advertise With Us page. We told ourselves it was because we needed more data, more analysis, more forecasting—but really, none of us wanted to pepper our smart, cutting, and inquisitive work with ads. (Our advertisements page spent its entire existence as an unpublished draft). In the end, our (or perhaps just my) decision to treat the publication as a project rather than a business caught up with us, and we had to close our doors. The socially progressive news & opinion blog was no more.

Through the sleepless nights of a baby who could only sleep after hours of rocking and singing Somewhere Over the Rainbow and the several pots of coffee2 I drank every day, my wife and I decided the best thing we could do for our brand-new family was head back to California—where we both were born in 1986, where we both fell in love, and where we both felt drawn to whenever we talked about the feeling of being home.

So with no job, no plan, and no way of knowing how the world would be changing over the next decade, we moved across the country to a tiny apartment in Corona. I had enough going on outside of new fatherhood to keep me too busy to reflect on how I could have done things better with my blog:3 graduate school, a hosting company, fiction, so many programming projects, and eventually a job in higher education.

From about 2014 to 2021, I dug deep into institutional research and education policy, started (and subsequently abandoned) a PhD in Education, taught introductory programming,4 and even helped build California’s first free, online community college. Somehow I squeezed two books out, as well: Data Science in Higher Education (a technical introduction to the R programming language for institutional researchers), and Evolved (a sci-fi thriller). Though I enjoyed tinkering and building software for myself, I did not, in fact, enjoy building things that other people thought I should be building. I was far too idealistic and opinionated to continue to find ways of operating successfully within the cognitive limitations of higher education bureaucracy.

One day I realized how much I missed writing. For the longest time, writing was how I escaped (when I was a child), how I coped (when I was a teenager), how I thought (when I was a teacher in the military), and how I grew (when I was writing about the American zeitgeist). Near the end of 2021, piggy-backing off of the niche corners online I found myself in, I decided to take a chance and shift away from building software toward teaching people how to use software. I found a remote job in technical writing (“developer education”) for an enterprise communications company, teaching developers how to write integrations, apps, and automations. It felt like the perfect coalescence of my energies: all of my love for the puzzles of writing software, wrapped up in my love of teaching and writing. Or so I thought.

As the mental dust of beginning my first private sector job since high school was settling, another dust was settling where I now worked. A recent acquisition for an unfathomable amount of money by a huge technology conglomerate led to a gradual shedding of the very people from whom our quirky but inviting workplace culture was derived. People from the parent company took over. Directions were changed. Morale tanked. Layoffs were announced. Morale tanked again. Product enhancements were refactored into potential revenue streams. Over the last three years, the tool I had once enjoyed using transformed under the pressures of what I can only interpret as corporate greed, following a pattern Cory Doctorow describes perfectly:

Here is how platforms die: first, they are good to their users; then they abuse their users to make things better for their business customers; finally, they abuse those business customers to claw back all the value for themselves. Then, they die. I call this enshittification, and it is a seemingly inevitable consequence arising from the combination of the ease of changing how a platform allocates value, combined with the nature of a “two-sided market”, where a platform sits between buyers and sellers, holding each hostage to the other, raking off an ever-larger share of the value that passes between them.

Something else that happened during this time was the systematic dismantling of the public town square known as Twitter—which had a much more profound effect on me than I had realized. Twitter was a company that I really wanted to work at for a long time because it was right at the intersection of many things that interested me about computers: technologically-mediated human connection; microblogging/content publishing; ethical dilemmas in content moderation; developer tooling and automation.

As a user, I’d been active on Twitter since about 2011, and when they decided to permanently ban Donald Trump’s account ten years later, my curiosity led me down the rabbit hole of social media platforms and how they worked. The fact that a serial fraud could manipulate voters through the technology we use to connect with each other was fascinating to me. On top of that, there was a whole ecosystem of open source responses to what I had once described on my since-deleted Twitter account as “the shitshow of walled gardens”; programmers and thinkers, alarmed and dismayed by the corporate monopolization of technologically-mediated social connectedness, collected themselves in communities that share knowledge via open protocols and networks of computers running open source software collectively known as the Fediverse.5

Now it’s nearing the end of 2024, and after three years at a company being steadily digested for its popularity and squeezed through the intestinal tracts of the corporate technology sector, I find myself resonating more and more with an article by Sheon Han on the death of Twitter. Some weirdness will persist, they write, and yet the weirdos will be gone.

When I came to the private sector I was looking for a place that would not only accept me for who I am, but that also had the courage to accept everyone for who they are. It started like that, or at least it gave off the impression of being a place like that, but what ends up happening when companies grow too big (or are bought and become part of a bigger company) is that things like diversity and inclusion change from being the germane backdrop for social connectedness among colleagues to being abstract concepts in neatly packaged mandatory corporate training that check compliance boxes. Of course, corporate culture is ultimately a function of the people involved; we each have to make daily choices to create a workplace worth showing up for. But after a certain point, too many quarters of performative corporate change lead us to crossing the event horizon, and even the cheeriest of cheerleaders have to pack it up and head on out, unable to continue our own illusion of still being what we were before everything changed.

I’m thankful for all the opportunities I’ve had to express myself and do things my way, and I’m grateful for the people I’ve met and the personal connections I’ve cultivated. But riding the hype waves at a software company just isn’t for me, and if I’m not careful, the commensurate mental exhaustion will erode my ability to recognize whether the work I do is personally fulfilling and intellectually gratifying—a process I’ve watched grow more suspiciously absent as each quarter went by.6

So I left my job last week; yesterday was my last day. For the first time in a very long time, I don’t have any employment prospects lined up. I have interviewed at a few companies over the last year, but ultimately I decided that I didn’t want to just jump on another train—I needed to get off the tracks completely for a while. Slow down. Take some time to read and write without the drumbeats of quarterly initiatives propelling my brain toward projects I really didn’t care about.

Instead, I’ll be spending this upcoming quarter:

  • Not thinking in terms of financial quarters (-1 point already)
  • Not thinking about generative AI (except in the concept of combating disinformation and misinformation)
  • Writing more
  • Reading more
  • Working on technology projects that spark joy

So here’s to that.

—Jesse

  1. I was learning how to be a dad, writing a book, growing a web hosting company, reading and writing papers for graduate school, and trying to master the Ruby programming language—all while applying for any job that would pay us a living wage. ↩

  2. It took over a decade for me to realize that this is a symptom of unmedicated ADHD. ↩

  3. graduate school I was getting an MA in English, focusing on feminist critical theory. hosting company I started a bespoke WordPress hosting company to generate revenue while running the blog, which was not, in hindsight, a great idea. Perhaps things would have worked out differently had I been less worried about generating revenue… From Future Me: perhaps the choices we make in the past are less about informing future regret and more about providing contextual clues during moments of self-reflection. fiction I’ve always written short stories, but it wasn’t until much later that I started publishing anything. If I had to put a finger on genre I tend to write, I would say it’s like Michael Crichton if he wrote speculative science fiction. programming I’ve been teaching myself how to talk to computers for as long as I can remember. The first source code I ever looked at was John Carmack’s work on Wolfenstein. I’m fully self-taught; never went to school to learn how to code. One day, I’ll tell the story of how I got started, since I think it’s important for everyone to understand that anyone can learn how to program computers. ↩

  4. You actually can’t teach computer science courses in California community colleges without either a graduate degree in computer science or what they call “the equivalent”—which was, last time I checked, math or business administration. There is one loophole, though, and that’s how I did it: if your department classifies computer programming courses as Computer Information Systems courses, then you only need a bachelor’s degree in any subject and relevant work experience. (It was a long time ago, so things may have changed, but that’s how I remember them). ↩

  5. The “Fediverse” is a group of interconnected social media platforms where users can communicate with each other, even if they are on different platforms. Think of it like different neighborhoods that all share the same roads—people can visit or send messages between neighborhoods even though they live in different ones. Each platform in the Fediverse is independent, like how each neighborhood might have its own rules and norms, but they all can still connect to each other. This encourages an ecosystem where users have more control over their data and choices, unlike with big social media platforms like Facebook or Twitter where everything is controlled by one company. That hasn’t really been true in practice, though—account portability, in particular, is far more theoretical than the pitch suggests. ↩

  6. My largest gripe with conglomerate software companies is how they use acquisitions as an innovation strategy. Most companies that sell products to solve customer problems need to augment their product (and certainly not just change for the sake of change), but when you have an unfathomable amount of capital, you can just buy other companies that solve customer problems instead. This gives you the appearance of having solved your customer’s problems, but integrates a new issue into your customers’ experience with your product: clunky multi-product friction. ↩