I’m thinking it would be worthwhile to simulate a conversation between Essayist Visa and Tweeter Visa. I’ll just freestyle it, calling them EV and TV respectively.

EV: It must be nice to tweet all day. Tweets are so easy to write. But don’t you wish you could write something more substantial?

TV: I do, actually. I’ve tweeted so much that I’ve reached the edge of what is possible with tweets. I’ve seen the limitations of the medium, the expectations of the readers. I’ve pushed this thing to its limit and I have chafed against it. I wish I could write essays instead, like you.

EV: Well good thing that we’re the same person, I guess! But honestly I’m not writing as many essays as I wish I did.

TV: Oh? What’s stopping you?

EV: Well, they’re harder to write than tweets, for one. You can just fire off dud tweets and not worry too much about them, if they get overlooked or even misunderstood, you can mostly laugh it off and move on to the next tweet.

TV: I don’t get it. Can’t you do the same with essays? What’s wrong with writing dud essays?

EV: I suppose you’re right. Intellectually I agree, it’s okay to write dud essays. But emotionally it feels worse. An essay asks more of a reader than a tweet, and so a disappointing essay feels worse than a disappointing tweet. You don’t even have time to get disappointed by a tweet; you’ve already moved on to reading the next one.

TV: But the flipside is also true, isn’t it? Most people don’t take the time to really appreciate a good tweet either, they’ve already moved on to reading the next one. That’s part of why I’ve been frustrated. I want to go deeper.

EV: That’s what I’m trying to do, but it’s hard! It’s not just that I have dud essays. So many of my drafts are unfinished. Another good thing about tweets is that you can’t really ‘overextend’ yourself. The character limit challenges you to containerize your thoughts in ways that don’t really spiral out of sense.

TV: True, but also containerized thoughts are intrinsically limited, too. It sounds to me like you need to figure out a way to resolve the “spiral out of sense” problem.
EV: Yeah, and I suppose the core thing about that is practice. And I’m doing that. I’m practicing. A lot of my practice has just been unproductive, at least in terms of end results. And I wonder if that’s just a part of the process, or if I’m doing something wrong.

TV: Generally speaking, how might one tell the difference between process that hasn’t borne fruit yet vs process that is wrong?

EV: You sly dog! That’s a great question. There has to be some sort of investigation about the process. Which I suppose I haven’t been doing very much of. I gotta revisit my drafts and ask things like, “what was I trying to do here?”

TV: Do you wanna do that real quick with your existing drafts?

EV: I think I’ll do that separately. But actually this is bringing up something else for me that’s related, which is that… there are essays that I feel I ought to write– but I don’t wanna!– and… I have this stubborn, precious part of me that wants to do something exciting, novel, delightful, something that feels like an adventure. It drives me a little insane that I’m not simply doing that already, considering that so much of my life up until now was me trying to get myself to this point.

TV: Why aren’t you doing it? What would you like to be doing?

EV: That’s part of the frustration: it seems to change every day. Sometimes it changes by the hour. I might start writing something that feels like it’s the adventure-of-the-day, and then get distracted by Twitter, and then when I come back to it I’m a whole different person and it no longer feels interesting or exciting in the moment. But as I talk to you about this I find myself thinking… that’s not the whole picture. I do have recurring patterns and interests that I return to. I kept returning to Aladdin for a while. For the past couple of days I’ve been thinking about the Kingdom of Aksum, and also camel trading routes. And also neon.

TV: Those certainly sound like Visa nerdposting essays waiting to happen!

EV: Exactly, so the question on my mind is, why haven’t they happened yet? I keep getting bogged down by some kind of perfectionism, which I find embarrassing considering that I’ve been writing for like 20 years now, and my aversion to acknowledging that embarrassment I think might be my primary bottleneck right now.

TV: Well, you’ve acknowledged it at least to me. Good job. What’s the next step?

EV: I could try writing about one of those things. I think one of the big mistakes I keep making is trying to write something Proper, which feels all stiff and gross to me. I should just dive right into the thing.

TV: Maybe! It seems to me like you have a lot of things going on all at once, and you’re being quite hard on yourself about not having figured it all out already. And particularly I want to point out that being hard on yourself isn’t working.

EV: Ahhh good catch, you’re right. What I should really be doing is laying out all the major processes. I’m also trying to pare down my notes. I’m also trying to write some memoirs, and do a “history project” that remains quite poorly defined. Actually all of my definitions are quite nebulous, which is a big part of why things are moving so slowly.

TV: What’s the most important thing you could define for yourself right now, that would help you move things faster?

EV: I feel like I might’ve already done this, but it’s one of those “if i can’t point at it confidently, it’s the same as if it doesn’t exist” type of things– I should articulate the specific essays that I wish already existed, and why, what jobs they do. This brings me back to wretchedness again, smartphones again… there’s a bunch of tidying that I could do to make my life easier on this front. It would probably help to have some sort of presentation, a public show-and-tell of sorts, maybe just for a couple of my friends. If I do it right it will also inspire them. But really I want to do this for me. I deserve to feel good about my work. I should experiment with being my own manager. I should shut down the operation for a few days to do some deep thinking.

TV: all the best!

EV: thx we’ll see