I have an Evernote filled with reams of notes going back years. The oldest note in there is from the end of 2011, though I started keeping notes regularly in 2015, when I was 26.
Eight years worth of regular notes, thoughts-to-self, personal reminiscences, problem-solving, ideas for projects, notable quotes, and tentative plans for the future.
In the past I would very frequently go through the notes I’d accumulated up until that point, begin conversations with myself (sometimes including several layers of comments within square brackets [like this]), and look for patterns. I still do this from time-to-time, though less frequently.
One very common observation I’ll make is that I’ll look over notes from a few years ago and think — damn, that was a really good idea. This isn’t mere self-flattery, the person I was a few years ago feels like a different person, and yet sometimes he’s ahead of me in a few areas. This is always slightly disconcerting — I’ll feel like I’m making progress, and then discover that I’m just now catching up with my past self.
Anyway, should I have pursued some of these ideas? Did I make a mistake not going after them? Was I too cautious, too indecisive?
Or was I too demanding?
Did I think the really-true-for-real-this-time pot of gold was around the next corner?
I don’t know. I did pursue many opportunities that just weren’t quite right. Something that seemed very promising, with one or two subtle niggling questions, would over time turn out to indeed be very good — in certain areas —but the subtle niggling questions would turn into raging soul-sucking chasms leading to the outer void.
Get out. Now.
I remember walking around Tokyo, four days after quitting my job in London, and feeling truly free for the first time in my life. It was a few weeks before my twenty-ninth birthday. I had enough cash in the bank to live cheaply for a very long time, and no pressing commitments whatsoever.
(A very odd feeling — I had taken about five months off work travelling around Asia shortly before I turned twenty-six, but I had more things to deal with during that time, so the rest from work wasn’t absolute. This time I really was free and clear. Even seemingly minor things, like the fact I’d already paid tax on all of the money in my bank account, made a huge psychological difference.)
What did I want to do? I wanted to write. But I still also wanted to do something big in technology. I knew that I could do something big in technology. The fact that people treated me as though I couldn’t do something big in technology had turned into a huge, smouldering, evil, ugly resentment.
I had freedom in every practical form that mattered — white, male (I’d never felt either excessive guilt or pride about those attributes, but I did come to appreciate that they made many things easier), educated, from a first world country, in relatively good health, with money in the bank, a professional career I could fall back on, young enough to travel, old enough to be respected and to know how to take care of myself or handle most situations, and a few promising ideas for things to work on — and internally I was a mass of seething, awful, writhing snakes of paranoias and resentments.
I don’t want to say that I was completely tormented the entire time: I was very happy for the first few months of freedom. My mind and body gradually began to unwind and I began processing much of the chaos of the previous few years. I did try to make the most of the rare precious opportunity I had, a combination of fortuitous circumstances, the accumulated effort of the people who built the modern world, and my own effort, courage and skill leading up to that point.
And yet, as the joy of experiencing freedom began to wear off, I was forced to realise that I really was deeply screwed up. I’d known this for a while but I was hoping things would wear off or that I just needed a proper vacation.
This was horrifying to discover. My screwed-up state began to feed into itself. I couldn’t make a final decision — writing or entrepreneurship — until I felt that I was in a better frame of mind. I couldn’t get into a better frame of mind until I’d made that final decision. I tried sketching out elaborate research notes to get clarity on this decision, but they only made the problem worse. The more I tried to concretise the different ‘paths forward’ available to me, the more confident I became that I could do something huge — and the more utterly screwed up I felt.
The deepest parts of me said that writing was the thing that I really wanted to do. The life philosophy I held said that I should pursue whatever brought me the most happiness. But how much happiness would writing have to bring me to overcome the wretchedness I felt? It didn’t seem possible. It still wasn’t out-of-the-question that I could pursue something huge in technology. People I knew who seemed less-than-impressive had achieved big things, and the people who did seem impressive had achieved enormous things.
How much could I achieve?
I’d been around long enough to have witnessed various technological trends move from glimmers in the eyes of a few researchers and visionaries, to white papers and scrappy prototypes, to fast-growing startups and hundred-million user apps, and finally to world-historical behemoths shattering the foundations of planetary civilisation. Everything I’d read about in weird blogs as an undergrad had come to pass — everything I’d read about in weird blogs in my mid-twenties was just beginning to make an impact.
(Seeing bitcoin, COVID and AI all follow the same cycle a few years later shouldn’t have surprised me too much — though it is still very odd witnessing the ‘conventional’ world gradually merge into the science-fictional world as perceived by internet-native weirdos.)
Could I really foreswear all of the above just to arrange a few words on a screen? Was that really such a valuable activity?
Writing out the above has made the answer obvious, but I could never have written this article four years ago. This is is the article I would send to my past self — though I doubt reading an article would have solved his problem. He/I had to go through the unending rock tumbler that was my life to get to the point where I could write this article.
Was that journey valuable?
Is this article valuable?
If it inspires any insights, are those insights valuable?
I’m beginning to see the answers.