Starting Again

Hi Everyone,

Welcome back to the newsletter after our brief hiatus.

For the next few issues, I'm going to be trying something a little different. I’ll be using a little known but allegedly powerful technique that people claim will improve the quality of my writing: Actually editing it.

Yes, I’m aware I might be considered a little behind the curve here. It’s true though: Editing has, so far, played a relatively small role in my writing. Almost every piece I write is written in one sitting. I sit down and write it from start to finish, do a very quick pass for clarity, and then I click publish. I might move text about and edit a little as I write, and I've often thought about the piece before I ever commit words to the page, but there is no drafting process to speak of, and the text rarely undergoes any sort of major revision.

Why do I write this way? Well, because I hate editing, and I tend to get distracted. My experience has been that if I have to spend a long time on a piece I will rarely finish it. Thus in order to get any writing done, I’ve adopted a model that allows me to work around those weaknesses.

It's a model that lends itself well to a particular style of writing - one that resembles off the cuff speech - and one that I’ve gotten quite effective at over the years, and can use to produce pretty good writing.

The problem is exactly that though: It produces pretty good writing. Writing like this I can be a good writer, but I can’t be a great writer, and I’d like to be.

I probably won’t ever be a “great writer” in the sense of publishing best selling books or winning prizes, but I would like to be great at the sort of writing I do, and currently I'm not.

(You don't need to reassure me and tell me I'm great. I don't feel bad about this, it's just an honest assessment of how well I'm doing by my own standards. I don’t feel like I’m falling short, I just feel like I can do better and I want to figure out how.)

Part of the reason why I'm only good is that I've plateaued. This model has been very good at getting me this far, but I've hit a local maximum where I can’t just keep making incremental changes to the process and expect to get better. To the degree that the current process can be improved, I cannot learn those improvements without trying something significantly different, and to the degree that my writing can be improved a lot, or expanded to longer works, it needs a new process.

Unfortunately, adopting that new process doesn’t mean that the writing quality in my newsletter is suddenly going to see a large improvement, because there’s a reason I’m not doing it already: It’s hard and I don’t like it.

If anything, in the short term my writing is likely to get slightly worse, because I’m switching from a writing process that I am good at to a writing process that I am bad at. Even if the latter theoretically produces higher quality writing per unit time, I’ve spent a lot of time getting good at the former so it’s not a like for like comparison.

This is, I think, a common and very general pattern: You get good at something by focusing on the skills you currently use to achieve it, but eventually you hit the point where you cannot get better without learning new skills.

This is very annoying, because it means that no matter how good you are at something you’re eventually going to start again and go back to being bad at it if you want to improve, because you hit the natural limits of how far you can go without the skills you’ve so far neglected, so now you need to learn those skills.

I don’t think this pattern is inevitable, but it might be optimal.

There are too many skills that one needs to be good at to achieve great results, and if you try to be good at them all up front then you will improve less quickly at each individual skill because you’re less able to practice them in an enjoyable and useful context. You will probably also waste a lot of time trying to be good at things you don’t currently need to be.

If you instead work on a subset of the skills, get good at them, and then go back and revisit the rest using those skills as a foundation (cf. Unusual Foundations), you will probably get much better than if you tried to get good everything at once.

If we were to put this all together in a simple slogan, it would be something like this: If you have something you’re good at, and you want to be great at it, you should first find a way to be bad at it.

Unfortunately, this creates a problem: When we are good at things, we tend to integrate the fact that we are good them into our identity, so not being good at them feels bad - we are in some sense failing to be our self, and the result is often cognitive dissonance and shame.

I can think of roughly three ways to deal with this:

Firstly, it’s useful to narrow this conception of our identity. e.g. I’m not actually “good at writing” in some generalised sense, instead there is a particular way of writing that I am good at. Some of that skill carries over to new ways of writing, but there’s no reason to think I’d be any better at writing, say, a book of poetry than I’d be at playing Chess - I can apply some very general skills to it so I can probably do OK, but I’m certainly not going to be good at it.

Secondly, it’s fine to be bad at things. If you’re never bad at things it’s probably a sign that you’re only trying things that are too easy. We’ve got a lot of internalised cultural messages that being bad at something important is shameful, but it doesn’t need to be (cf. Norms of Excellence).

(It’s always far too tempting to blame everything on school, so I will be virtuous and assume that this has nothing to do with the way we force everyone to spend most of the first 20ish years of their life in environments that conflate learning with evaluating your worth as a human being, and that treat difficulties as your failure rather than that of the people whose job it is to help you overcome them. OK maybe I won’t be that virtuous.)

Thirdly, it’s OK to feel bad. It’s not the end of the world, it’s just an opportunity to practice discomfort tolerance. If writing permanently made me feel bad then that would be a problem (cf. Pain is not the unit of Effort), and would most likely result in my writing less and/or being miserable, but it’s OK to pass through a state where I’m currently frustrated and annoyed with my writing if it’s a temporary thing that enables me to do better or solve some problem (cf. The State of Being Stuck). This, too, shall pass, and eventually I’ll figure out a way to be good at editing.

This will get me to the next level - it will expand the set of writing projects I can meaningfully work on, and it will improve the quality of my writing in general. I expect it will take a while to get really good at it, but once I’ve got into the rhythm of writing this way and feel comfortable doing so that’s just a straightforward matter of practice.

After that, once I’m good at it, well, then I’ll just have to find a new way to bad at writing.