I’m most comfortable hammering out posts of five hundred or so words. That’s enough space to share an interesting link or suggest a connection between things, but not to develop ideas that feel like my own. Yet when I try to write at greater length, I get stuck in a vicious cycle of self-criticism and rewriting tangential paragraphs. Writing has been a big part of my identity since I learned to read and so the frustration of pushing out of my comfort zone ends up also threatening my sense of self.

I’m tired of being limited by this struggle. I intend to look directly at this discomfort and fix it — or at least figure how to engineer around it. Otherwise, I will spiral between aspiration and disappointment indefinitely, and that is no way to live.

I’m working to get my newsletter (“The Marginalia Club” — see footer for a link to subscribe) published on a regular cadence, but I need more than a regular deadline to break out of my five hundred word bottleneck. Without otherwise changing my habits, I’ll just panic and write the same old kind of fragmented five hundred words every time the deadline rolls around.

Austin Kleon has a method of nested journalling practices, using his “notebook turducken”:

I carry the pocket notebook all day, scribble stuff in it, take notes. It’s basically a scratch pad. Then, every morning after breakfast, I open up the pocket notebook, check my notes, then I fill out my logbook, which is sort of like an index of my days and a memory refresher. Then, I write and draw 3-10 pages in my diary, based on my notes and my log. I cross off things in my pocket notebook after I write about them. The diary then becomes a place I go to when I need new writing and blog posts.

I’m plotting out my own version of this, but building from the raw material of my highlights, underlined passages, and marginalia in the things I read. All of those things go into Evernote, which I think of as the compost bin of my interests.

I spend a little time every day browsing Evernote and free associating between notes. Notes from a blog post trigger a “this makes me think of…” hunch leading me to a related book, which leads back to another article from months earlier. If I get a good chain of hunches going, I copy the highlights to a Scapple board, map out the connections, and keeping riff on the theme.

Once I feel an argument form, I try to linearize it into an outline. I intend to bounce back and forth between the collage and outline until the argument seems sound and the structure feels ready. At that point, it’s time to write a draft.

I haven’t yet made it all the way through this cycle. I tried drafting my next issue yesterday, but got stuck pretty fast. The key now is stop beating myself up and get back to the outline. That failed draft just means I haven’t reached escape velocity yet.