I have been writing for more than 30 years and I know that some outlining is done unconsciously while staring at a blank computer screen or piece of paper. But the tougher the subject is to write about, the more having an outline on paper can help. The technique called branching is often a good way to start. (See How To Get Started Writing Your Memoir.)You can turn your branching work into a more formal outline as needed. But you will probably find that once you start to write your unconscious will take over the organizing function, so do not feel like you have to slavishly follow an outline if your unconscious is telling you to do things differently.
I find it useful to list the points I want to cover in any piece and then tick them off as I complete writing about them. For example, if I were doing a short essay on the foods of my childhood, I might have these points:
My mother’s cooking
My aunt’s cooking
Sunday dinners
The creamery down the block
Eating graham crackers after school
We all hated liver but Mother thought it was good for us
The Thanksgiving after my sister was born
I could use this list to help me remember what I wanted to cover in my essay and launch into the actual writing fairly quickly. There would be some rewriting as I found that things that seemed to belong at the beginning were really better in the middle or near the end, but I would avoid the tedious job of formal outlining, which for me has always hampered, not strengthened, my creativity. In my career I’ve usually had to write a specific number of words for a specific piece, so I probably also would determine how long I wanted the piece to be, and then assign tentative word counts to each item listed, to help me determine how much emphasis I wanted to give to that item. My “outline” then would look like this:
My mother’s cooking –250 words
My aunt’s cooking – 100 words
Sunday dinners –50 words
The creamery down the block – 50 words
Eating graham crackers after school – 25 words
We all hated liver but Mother thought it was good for us –50 words
The Thanksgiving after my sister was born — 50 words
That would give me an essay of 575 words, and with a compelling lede it would be just about right for a 600-word essay assignment. Of course I wouldn’t stick to the word count that I had assigned to the various topics, and I would remember other things about my childhood foods and eating habits as I wrote, but this short exercise would speak to my unconscious and get me started on the essay fairly quickly.