When I was barely a teenager, I remember I would excitedly rush to the school library during recess time, so that I could update my blog. What fascinates me about this memory is how pure that motivation was. I had no expectation of being “good”, of being “successful”, of “growing my following”, anything of that sort. I did it to do it. It doesn’t even feel right to say “I did it because I wanted to do it”. Because I wasn’t really conscious of the wanting. I might occasionally have had some form of the thought “I like writing, might be nice to be a writer someday”, but that feels like a kind of retroactive narrativizing – I don’t think it seriously occurred to me that I could be a writer. It gets more complicated if we dig into questions like “what did I even think a writer was, really?” I don’t think I really thought of myself as a writer in the earliest days. I do remember thinking of myself as a “webmaster”, but that was really just a phrase that I’d seen around on the internet that people used to describe themselves when they ran their own websites, personal or otherwise. I wanted to be one of those guys. And by having my own website, I was one of those guys, so there wasn’t really any particular ‘reaching’ or ‘ grasping’ or ‘yearning’. I was living the dream, at 13. I liked being on the internet. I liked feeling like I was a participant in what I perceived to be a grand game. I do remember that I fantasized about owning and running my own cybercafe, which I guess was my way of visualizing what the next step was.

What’s the point of sharing this memory? Well… I wanted to think about how it’s developed over the years. As I grew into my teenage years, I became more conscious and aware of things like social status, and boy did I want it. I never really cared that much for money, but status, acclaim, admiration, those seemed like things worth striving for. Specifically in my case they seemed like they would be the solution to all my problems. In real life, I was always a hypervisible misfit (tall, dark, unique name, etc), and I never really felt like I belonged anywhere. Over the years I’ve learned that loads of entertainers felt that way. We learn to perform for some semblance of affection, we perform in the hope of feeling seen and heard, we perform in the hope that admiration can be transmuted into belonging. (It kinda can, but not as much as you might hope.)

I remember seeing what was popular online, and I remember thinking that it didn’t seem out of reach for me. I could write just as well as any of those people, if not better. So I kinda just got to work, writing on the internet, with some vague sense that I’d surely reach some level of fame, and that it would mainly be just a matter of time.

As I got closer to adulthood, I became more conscious of the fact that I would have to find a way to pay the bills. My social environment nudged me towards aspiring to be a lawyer, or an academic. I tried those aspirations on, but they didn’t resonate strongly for me. I do remember wanting to be a games journalist, because I liked games and I liked words. At some point when I was working part-time as banquet staff at a hotel (to save up money to record my band’s CD), I staffed an event for local media, and I felt like I wanted to work in media. I devoured piles and piles of magazines when I was about 15-16, and I began to fantasize about being a magazine columnist. I was also broadly interested in education, but I didn’t really want to be a schoolteacher. That was sort of a last resort thing for me. At some point I fantasized about working as cabin crew for an airline, so that I might be able to live out a fantasy of writing on a laptop in fancy cafes around the world.

What did I want to write? Initially, when I was just blogging for myself and my friends, I was basically writing autobiographical slice-of-life snippets. A handful of times, I found myself writing about “social issues”, and about local news and politics, and I got more attention for that, so I felt compelled to do more of that. I was also quite inspired by the early wave of bloggers, many of whom seemed very focused on self-help, and I picked up a bunch of that by osmosis and imitation. I got interested in things like marketing and persuasion and storytelling, which seemed like a good fit for me as a kid who loved mythology and fables, who was growing into an adult who was going to have to make a living somehow. I did also admire STEM– I’ve never been a STEM hater– but I’d witnessed the people who had a strong affinity for it, and I knew early on that that sort of thing wasn’t quite right for me to build a career out of. I liked the idea of it more than I liked it directly. (That said, one of my first tastes of early virality came from pointing out a misuse of statistics in a local newspaper.)

I ended up getting hired, on the merit of my online presence, to run the blog and marketing efforts of a software company. It was a great experience for me, and it really challenged me to think more rigorously about working with goals and desired outcomes. I spent 5.5 years doing that, and then I left to do my own thing, which I’ve been doing for 8 years now. My plan was initially to try and write for online publications, but I never really followed through very much on that– I quickly became far busier just tweeting. From 2018 to maybe around 2023, I tweeted something like 200,000+ times. I cultivated a reputation for it. Internet friends flew me across the planet to hang out with them. I wrote a couple of ebooks which people have collectively spent $100k on. It felt like I was on quite a roll. This is where you might expect a sentence like “and then everything changed” or “it all came to a halt”. But… it wasn’t anything dramatic like that. When I look back at old notes, old tweets, old journal entries, I can see that I was already beginning to grumble around maybe 2022 that I wasn’t really enjoying twitter as much as I used to, even before the Elon takeover. Sure, when my favorite tweeter vgr stopped tweeting, that was sad. And then in 2023 my wife and I had our first kid, which dramatically changed my life in ways that I’ve written about elsewhere. It didn’t really make sense for me to spend all of my time and energy tweeting anymore. I do still tweet, but I no longer think “how do I get better at tweeting”, “how do I win over great new mutuals” and so on…