Writing for your worst self

· Around 3 minutes

The other day, I came across Adam Mastroianni’s great post So you wanna de-bog yourself where he outlines all the various stories that he tells himself when he’s stuck.

A lot of that was stuff that all sounded very familiar but it also reminded me about an unwritten rule that I like to keep: Writing for your worst self.

When asked how I learned a bunch of stuff that I know, I usually like to use the term “osmosis” by which I mean having spent hours reading and generally “soaking” in lots of information over the years.

Most of it didn’t make very much sense to me at the time, and a great deal of it still doesn’t, but you slowly build up a mental model of the thing you’re interested in and more importantly, a map of all the stuff where you say yourself “Ah, I know that X exists and I don’t know anything about X but it seems like it might be useful for this particular moment”.

There are a great many ideas along the way as well that just never made sense, got dropped by the wayside only to come across them years later and they seem a lot clearer.

Part of that is not that they actually are any clearer so much as you realise the core idea itself is actually really straight forward but has been caked in layers of nonsense that makes it seem much more complex than it really is.

Probably the biggest issue I have with is using all sorts of fancy grammar, which I’ll admit can be a bit hard of a balance when deciding whether to use jargon but for general language, I prefer to keep it dumb.

Supposedly there’s some school of thought that the denser and more sophisticated your writing style, the more “professional” it is.

That could be true but I’ve never felt that it was professional because my brain was too busy maxing out its resources trying to translate fancy words into normal words on the fly to notice.

If your normal self struggles to read fancy prose and dense content, your worst self definitely isn’t going to handle it much better.

Alternatively, you might be relatively fine but you’re trying to transition careers, picking up a hobby as a sort of second job so you probably need all the help you can get.

If I had to boil it down further to a simple rule of thumb, it’d probably be “Can I read this post at 3am”.

Well, I mean could you read it really, because I just hit publish on this stuff and rarely look back at it.