Going Through Old Notebooks Part 2: The Birth of the "Five Things" Prompt

Going through old notebooks, Part 2.

Yellow tulips, digital painting. iPad and apple pencil. c. 2025.

Dear Reader,

If you have followed me for a while, you know that when it comes to writing exercises, I am a great fan of a prompt I call “five things.” It’s not an especially original concept., but the idea of writing these five things was what got me started on Substack in the first place. It helped me get back to a kind of personal writing that I’d been missing, back in December of 2020, when I, like many people, found myself at a crossroads in life, in a dark and uncertain time, and needed something to hold onto.

This is what I wrote about my decision to engage in the practice then—I was nervous, I think. I didn’t want anyone to think I was claiming to have invented the idea:

“Back in the olden days of writing on the Internet, a group of writers I knew would often write brief essays or nonfiction blog posts structured around a list of “five things.” These “things” were usually observations, thoughts, confessions, referrals, or investigations. Each thing could be many paragraphs, or just one short sentence. I don’t know who originated the form. It might have been adapted from the fanfiction trope of the same name, which goes back to the early 1980s, in which five scenes are presented from a story or relationship. It may also have come from LiveJournal blogs of the early 2000s, out of which emerged a popular type of entry called “five things make a post.” Or it may have developed separately, a kind of writerly convergent evolution, a carcinization of words, like how different animals keep independently evolving into the shape of crabs, over and over again in the dark depths of the seas; creatures forged by the same environmental pressures. But regardless of where it came from, I find it to be a good way of getting thoughts down. There seems to be something about the number five that helps to give a satisfying structure. As I find my way back into regular online writing, I’ll be using that again here.”

Well, this is one plan for my Substack that I certainly stuck to!

xo

S