I’m taking a test prep class and during tonight’s class, my breakout room shared our answer to a constructed response task. I had volunteered to do the typing, and I got a compliment from a group member about my outline. Later, when we shared, one of the advisors praised the structure and content as a good answer. So I felt good about that.
My particular fascination with outlining came well after I’d finished college, when I found myself in a professional development session and I decided to write with Omni Outliner. That particular program is amazing and weird and challenging to use, but I have always liked it. What came next was a succession of plaintext and markdown files that offered more or less outliner-friendly affordances. The last outliner I got into before I began my experiment as a Windows user was Bike: I remember the palpable sense of dread I experienced imagining how I was going to prevaricate about which outliner was right for the task. 1
I actually don’t outline quite as much as I used to, because while outlines are incredibly helpful at structuring your thoughts and knowledge, they are inflexibly hierarchical when you want to connect ideas2. I’m currently of the opinion that the best notes are handwritten, a collection of thoughts and facts that may be outlines in large part, but with jottings and arrows and other leaps of thought scattered across the canvas. I like OneNote right now, but there are plenty of contenders on Windows and the Mac.
Word doesn’t have an outline mode in the sense, but it does a fine job formatting them. No folding though.
1 There are technical considerations to make besides which outliner to make, depending upon the app you’re using. Drafts makes a dandy outliner, but unless you leave everything in Drafts, you have an export decision to make. Other applications, like WorkFlowy, are their own silo of data and represent another location to search when you realize you need something. iAWriter walks a weird line between the two, allowing you to specify additional file locations besides its default library.
2I don’t want to ignore backlinks in apps like Workflowy and iA Writer, though; this feature alone found me adopting Workflowy for a time. If I were glued to my desk all day, I might have found more use for Workflowy.