Writing used to be easier for me. When I was a novice, when I was younger, when I perceived myself to be a nobody with nothing to lose and nothing to worry about. I remember when I was a teenager and I would just blog about whatever was on my mind, whatever I did day-to-day. I did it partially to hang out with my friends, partially for the pure joy of self-expression, and partially in the hopes that somehow something I wrote would matter to someone someday. I would post on forums, responding to whatever was happening ‘in the world’, whatever was on the news, sharing my thoughts and feelings without too much tedious meta-thinking about what it was all for.

Relative to how it feels now, it felt simple, easy, inconsequential. The “inconsequential” part did haunt me – I was thirsting badly for meaning and significance. I remember every wistful 3am moment humming with silent possibility as I thought “I want more out of this life.” In some ways, I have since been bestowed precisely what I wished for. So you could say that this is a screed of a man complaining about the troubles that come with getting what you want. How vain, how frivolous, how tone-deaf! And yet, I know in my heart that my younger self would have devoured such an essay from an older version of himself, so I’m writing this for him.

I do remember that in my early 20s I started to get a bit self-conscious about my writing. I’d besiege myself with questions like “What is a blog for?What is the point of a blog when there are hundreds of thousands of other blogs by better writers?” And I now have a pretty good answer to that. Not everyone wants to read the best writers; some people want to read from intermediate or even beginner writers who are still figuring themselves out, still grappling with questions of voice and subject and frame. We can always read the sacred texts written by the esteemed authors of the past, whose busts gleam with the adoration of ages of men, and yet that never quite scratches the itch of needing to be comforted by inhabiting the mind of a friend.

(I got a lot more questions where that came from, too. What is the utility of the written word? What is the point of discourse? When I was writing my 2nd book I found myself seriously wracked by the question of, What is a book even, really? Why should this particular book exist, and what configuration should it exist in? I have a deep-rooted impulse to go to the source of things, to try and understand the origins, and it’s often been a source of frustration for me – but it’s a frustration that bears fruit, eventually, over time.)

Looking back I can also see that I was starting to have ‘professional concerns’ – I was no longer just some kid mucking about, I was an adult with bills to pay, a spouse to look after, and I felt compelled to start thinking about my ‘career’ or my ‘trajectory’ in life. What was I doing? How was I going to eat? And would I regret it if I chose the life of a street busker, just getting by day-to-day? Even as a teenager I remember being besotted with visions of glory. I knew in my heart that a corporate life wasn’t for me. I earnestly felt in my bones that I would rather die than wake up every morning to put on a shirt-and-tie and suffer through the indignity of commuting. I know that lots of people say this sort of thing in a dramatic fashion, in moments of exasperation. I can’t speak for them, but I can tell you that I was actually serious, and I was plotting my jailbreak from ‘the rat race’ from the moment I had to begin serving my sentence as a student in public school.

Still. While I’ve continued to get better with all of those things, something else has gotten harder. I’ve been writing for about 20 years now, and a part of me feels like “I should be better already”. And here I’m reminded of some really nourishing advice from even older, more enlightened creatives like Kenny Werner and Stephen Pressfield. Pressfield says to “take some pressure off yourself, enjoy the trip”, and Werner points out that thoughts like “I should be better already” come from the ego, and that you can’t improve if you’re fixated on that sort of unhelpful self-flagellation. “I should be better already” is almost a subtle trap that’s designed to keep you where you are.

As I write all of this, a part of me cringes and thinks, look, I’m writing about writing again, instead of writing about less navel-gazing, less self-indulgent things. I know that some people will always be drawn to this sort of process examination, and a ‘dangerous’ outcome that I want to avoid is, spending all of your creative life discussing creativity instead of being creative. I don’t want to be running a talkshop for would-be adventurers to discuss hypothetical adventures, I want to be out adventuring. Maybe I’m a little harsh on myself. I’ve written two books, hundreds of blogposts, thousands of twitter threads. Is that a crutch? I’ve been thinking a lot about the necessity of facing things “naked”, discarding one’s plans and drafts and just diving into things, raw-dogging reality.

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blocked vs jammed

Scurvy used to be a problem. And then it got solved. And then the solution got forgotten, and it became a problem again.

I’m reflecting on this when thinking about my own relationship with my creative process. I used to write essays all the time when I was in my teens and early 20s. Then I stopped, and I think I partially forgot how to do it. And now I’m trying to learn again what I have forgotten.

<Meditation for engineers.>

What exactly have I forgotten? One is the joy of play, of exploration, of diving into the unknown with confidence without knowing where you’re going. Another is being willing to eagerly “abandon” drafts.

Occasionally I get flashes of wisdom. I try to write these flashes down, in part because they feel so precious, and in part because I hope that they can guide me later. I think of them as buoys or beacons that I can put up in times of clarity, so that I may navigate by them in the fog.

“Make elaborate plans and then do whatever you like” was one such flash. Another was “The problem isn’t that you don’t finish, the problem is that you get jammed. What matters is that you keep going.”

I’ve been feeling very jammed lately. My mechanisms are faulty, stuck, I need to take them apart and clean out the dirt and oil them and put them back together again.

Quick subtle note about synyonyms: I like the word “jammed” more than the word “stuck”. They can be used interchangably, but “stuck” makes me think of a stick in the mud, a bog, whereas “jammed” makes me think of a more complex mechanism. Also consider phrases like “signal-jamming” and “culture-jamming” – I’m experiencing interference, something is messing with my signal. Both words at once: Being stuck in a traffic jam. The road is all jammed up, and I’m stuck in it.

It’s subtle. Maybe a meaningless distinction to some people. But it feels meaningful to me, because of the associations.

I’ve written elsewhere that “being embarrassed about being stuck prolongs the stuckness”.

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(here’s an interesting older stub from before I published Are You Serious, which is the 2nd or 3rd in The Essays)

I try not to talk about it too much, but I have very high aspirations when it comes to creative work. I’m almost embarrassed to get into the details. I’d rather demonstrate over time. Maybe when I’m in my 70s I’ll say more about why I have high standards. Or maybe when I’m in a social context where it feels right to talk about it. I’ve definitely talked about it in some private conversations, but I don’t want to write about it. Why? A big part of this is that you can’t control for how someone might read your writing, what assumptions they come to it with. You can’t correct someone’s misinterpretations if you don’t know who they are, and trying to do so can actually make things worse. A conversation is a much more intimate space, and it’s a two-way back-and-forth, which makes all the difference. I don’t get to ask my readers followup questions.

I’ve been thinking very hard about what I am doing with my essays now, for over a year. I’ve been thinking about it vaguely for over a decade. When I say “my essays”, right now I’m referring specifically to this substack, but really I’m referring to something a little more “elevated” – I’m thinking about The Essays that will constitute My Body Of Work at the end of my life. I should probably be the leading authority on my own work, and as long as I don’t die suddenly in a freak accident, I should probably have time to lay out what I think My Essays are.

What you are currently reading is the 5th post on this Substack, but I think only the first one – We Were Voyagers – really makes it into “The Essays”. I’ve written other things that should make it into The Essays – The Library Ethos is one of them, it happens to be published on my blog. In 2014 I wrote an essay on Medium titled An Analysis of Power and Social Dynamics In ‘Mean Girls’. A month before that I wrote a an essay titled Letter To A Young Songwriter on my separate /1000/ writing project.

A twitter thread is not necessarily an essay. Some of my best threads might maybe qualify as essays…

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I think it’s fair to say that most writers hope to be read.
There is certainly something sacred and beautiful in writing just for oneself— some of my most precious writing will never see the light of day, and I would keep it that way.

But language is a communal enterprise, and humans are social creatures, and so it makes sense that many of us who write, write so that someone might read us.

But it’s also certainly more complicated than that, and here on I’ll just speak for myself. I’ll split this into several parts?

History of my writing

It’s hard to identify precisely when I first started writing, because it was all a bit of a blur. Some of my earliest writing happened in various Internet forums. I wrote a couple of guides for GameFAQs, which I was inordinately proud of. I wrote an article for the Neopian Times at neopets.com. I wrote Digimon poetry for a Christmas contest. I wrote compositions for school, and I always relished at how I was able to bend the rules of what the teachers insisted we should do, and still get excellent grades. I started a blog when I was about 11 years old, to keep up with all of my friends who did the same. We’d mostly just talk about our daily lives, although from time to time we might’ve veered into doing something like social commentary. The blogs of the early 2000s had a certain style that’s hard to properly explain – irreverent, intimate, chaotic, personal…

I’m tempted to look up and reference past writing I’ve done about my writing. I’m sure I have several snapshots over the years. But I think I should “write the rest of this” as much as I can

I grew up reading as many books as I could get my hands on.