Objectives: Dig into how I write and see if I can dislodge something that can be improved; connect with other people who sometimes struggle with writing to show that hey, they’re not alone.

I’ve been experimenting with writing headlines first. That’s a popular blogging tip: come up with two or three headlines, and you might find that the rest of the blog post writes itself.

Except that most of the time, I don’t know what I want to write about until I start writing it. Maybe the blog post is about a technical problem that I’m still trying to solve. Maybe it’s about a personal question that I need to explore. Maybe it’s even a bit of both. I write and write and write. It takes shape. Then I cut out what doesn’t belong there any more, come up with a title or two, and stash the clippings for a future post.

I still haven’t figured out how to write to an outline or a plan. I wander. My occasional attempts at having daily themes for my blog dissipate after a week or two, with the exception of my weekly review. Instead, I write whatever comes to mind, although sometimes I schedule the posts apart so that I’m not writing about the same topic four days in a row.

I write from the bottom up, one chunk at a time, gradually bringing ideas together with links and categories. Now that I think of it this way, it makes a lot of sense. A wiki lends itself to top-down writing, because you can link to pages that don’t exist. Blog posts tend to link to the past, instead of the future.

Part of it is because I like taking a closer look at topics, ignoring the big picture in favor of detail. I’m less interested in mapping out the entirety of a space, and more interested in answering one question at a time. My questions tend to be bite-size. I don’t dwell on the overall structure of an area. I ask: what’s the smallest thing I could learn in order to move forward? This is great for learning and for making progress, but it might be hard for other people to follow.

• How can I experiment with this so that I can gradually get used to writing with a plan? Every so often, I make an outline of things I’d like to write about, but I tend to ignore this outline in favor of other ideas that come up. Persistence and experimentation, perhaps.
• I can leave more notes for myself, reminding me why I was curious about something. I can write with a checklist – even if it means filling in objectives and calls to action after the post is drafted.
• I can get better at stashing snippets so that I edit more ruthlessly, and maybe I might even file those in these words somewhere in my outline. Probably Org Mode, then, or maybe Evernote with tags.
• I can tell people what my plans are, so that people can give me feedback on whether it works for them. In deliberate practice, it helps to call your shots.

It would be good to learn how to write methodically, to survey the land from a high point before whacking my way through the jungle, to define landmarks that can help me see my progress.

Other people have figured it out. I can learn how to do so too.