Image: sunaxhs (synaxis.bigcartel.com), found via Reddit
For a long time I’ve been chewing over the past. It’s almost certainly not the healthiest habit.
But just telling myself to stop chewing over the past doesn’t make me stop. I heard one of those annoying online therapy gurus makes an annoying comment that was annoyingly accurate: you have to be careful not to judge yourself for judging yourself. And, it’s safe to say, also careful not to judge yourself for judging yourself for judging yourself, and so on, ad infinitum.
The best way to break out of these loops (I found) was to understand the root cause of the constant self-criticism more clearly. But it also helps to shift perspective.
When I was twenty-four I was not very happy. I had not launched my startup career. I was in a job where I was under a lot of pressure, felt like I wasn’t delivering, and couldn’t see the way out.
Had I wrote out my options at the time I’d have thought of them something like this:
Option 1: try to start work on some startup idea at the evenings and weekends. Con: after leaving work and taking the one-hour commute back home across London, I had about four hours to myself each evening if I was going to sleep at a reasonable time. After writing code all day, it would take superhuman willpower to use up a decent chunk of my brief free time to write more code.
Realistically I needed to take at least Sunday off or I would have burned out rapidly. (I tried working 8-12 hours/day, 7 days/week briefly when I was twenty-three, but it was horrendous for my health and not sustainable.) So that left pretty much just Saturday and maybe two or three evenings to work on my own ideas. It would take a long time to get anywhere. And I wanted to get out!!!
Option 2: jump ship and try to immediately get into some startup accelerator or find some other source of funding. Con: my stubborn pride wouldn’t let me take outside funding immediately. If I took a shot at going it alone I wanted to get as far as I could under my own power before giving up ownership to someone else. I was an engineer, the priest of the machine! I knew something about business (unlike most nerds) and I knew how to build (unlike most people in business) and I wanted to take full advantage of this edge.
Option 3: jump ship and live cheaply off savings while building my own ideas. Con: Though this idea appealed to both my romanticism and sense of scrappy independence, I had to admit that I was a terrible procrastinator. When I lacked outside pressure I rarely accomplished much. (This wasn’t entirely true — in the past I had in fact accomplished a lot on my own steam, but it had to be a project I was sincerely interested in — and I hadn’t completely identified this connection at age twenty-four.) I had a vision of myself screwing around and watching my bank account dwindle while my anxiety greatly rose.
At this point I’d usually start considering option 1 again, but I’d try to figure out some way to trick myself into getting started, and simultaneously figure out if I could quickly build and validate some basic idea without needing to write too much code. (Yes, I was very familiar with Lean Startup ideas like building an MVP, launching quickly, iterating, and so on. I just tied myself in knots developing ever more elaborate startup ideas while procrastinating on sharing them with people.)
Looking back, how could I have gotten myself out of this awful tangle?
There were probably several causes underlying my deficient thinking, but another factor that wasn’t helping was my ongoing negativity. My job was draining me. I didn’t socialise much, didn’t exercise regularly (besides walking all over the city on weekends) and spent a lot of time reading quite dark, intense and intellectual writers (people like Nick Land, Chris Bellas [The Last Psychiatrist] or John Michael Greer [The Archdruid Report]).
Some might say that maybe that was a closer reflection of my actual interests than the peppy, positive world of startups, which could also be very often shallow, self-indulgent, or uncritical. Indeed the idea I thought about the most at the time was some kind of aggregator for more “serious” online writing. It’s interesting that I’ve almost come full circle since then.
Anyway — there was something very cool about many of the writers that I read. They had an interesting aesthetic. There was a kind of unorthodox underground feel to many of the weird blogs around back then — and not only the political blogs. I believe the early ‘10s were something of a tipping point for internet usage (remember that this was the era when smartphones had just taken off in a big way). People in the “rationalist movement” were discovering psychedelics and meditation — this was quite a curveball at the time, and it meant that “rationality” bloggers and meditation bloggers began to overlap. Cryptocurrencies were lingering in the background (though pretty much only bitcoin had any traction back then), and were just beginning to gather steam — and you probably wouldn’t hear about any of them in any depth unless you went hunting through lots of weird crypto blogs. Very very cool to unearth all this stuff at the time though.
I definitely thought there was something in all of this weirdness, but I didn’t know what. The trouble was the dark, cynical mindset that many of these extremely-online writers seemed to cultivate. Absorbing that mindset was fun, in a peculiar way, but not conducive to getting much work done.
Initially I was going to conclude this article by writing that had I stayed more positive I might have figured out a better solution to my predicament. Actually, having wrote all of this out, I realised that part of me in fact liked the darkness and negativity. It was cool, interesting, transgressive. The world of startups in particular was too cutesy-wootsy, too blandly upbeat, and tended to lock away some of the seamier sides of life. The underground writers, in contrast, felt real.
I don’t actually have a conclusion to this article. Some days I just sit down and write about whatever I’m thinking about. But there does seem to be something to this clash between the positive and the negative. Why am I drawn towards the negative?
I know a certain crowd on Twitter likes Carl Jung and some of his ideas on the dark side of the psyche. I think this is something slightly different though. I’m not so much focused on personal darkness, but rather on dark worldviews — or at least worldviews that are slightly darker than the norm.
Re-reading such material now takes me back very strongly to age twenty-four — that age in particular was when I was most focused on such material, and also the age when I felt a near-constant desire for freedom. Dark, rebellious, and transgressive theories were the antithesis of the stupid boss I had breathing down my neck for most of the working week. Reading such theories was liberating — power and freedom, life and truth, the joy of exercising an independent mind.