How do you make it stick?

I’ve been thinking I should write more. I don’t like thinking in shoulds, but it’s pretty human. The real question is whether I want to write more, and what to write about.

In my lifetime, I’ve tried a number of diary-style blogs, helpful-hint blogs, MySpace posts, professional posts (here! on Medium!). I even tried setting a daily calendar reminder to journal, in an effort to improve my memory. Nothing seems to stick. How do you make it stick?

I grew up loving to write. Then in college, when I got yelled at by a newspaper EIC who told me I’d never have a career because I asked a source to stop harassing me, and when I got accused (falsely AND not formally, so there was no resolution) of plagiarizing a music history term paper because “it sounded too smart,” I felt like maybe I didn’t love to write. Or maybe I shouldn’t love to, since I was apparently so bad at it. But one thing I was indisputably good at was following grammatical rules. So I did a lot of editing.

Several years later, I tried writing freelance, but it was a really spur-of-the-moment thing, I didn’t have a client base built up, and it turns out I really need externally provided structure to get work done, even work I like. Absent structure, how do you make it stick?

I write for a living. I context-switch all day everyday, so I always have something new to write about. But it’s always fact-based, and I’ve always preferred that exposition, creative or not, of my life and what’s in it to making things up. Never could tell a convincing lie.

But I’m a decent writer, and I’m envious of friends and peers who write fascinating essays and spin glorious tales, about content strategy and other things. So I selfishly want to be able to do it, too. They made it stick, but I’ve been too shy to ask how.

I’m asking now. How do you make it stick?