My hate-love relationship with outlining - the trials and tribulations

How decades-long abhorrence finally turned into enthusiasm and appreciation (and re-awakened my tenacity and perseverance)

This is the first in a two-part series. Part two has dropped. It highlights “how one magical experience helped me realize what I had been, and was again, doing that kept me stuck.“

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Saying I don’t like outlining is an understatement of epic proportions.

I abhor it. Actively hate it. I’ve tried it time and again. And it’s doggedly refused to gel with how my brain works.

Cognitively, I know I need to outline a piece before writing it if I want to get any of the purported benefits. I’ve known that since my first article writing course all the way back in the early 90’s.

But all of the advantages — I’ll get to them, I promise (in part 2) — have eluded me time and time again. Dangling in front of my nose like the proverbial carrot, only to keep pulling their nose at me like kids in a playground.

Until a couple of weeks ago.

I’ve finally unleashed the outlining magic upon my writing routine. Unlocked the secret to making it work for me.

I’ll let you in on it, but first, let me talk you through what I tried and didn’t work — at least not for me and my brain.

I read a gazillion articles on outlining.

Most are superficial at best. They’ll tell you to list the stuff you want to include and the points you want to make for each.

That’s like “D’oh!”

And don’t count on the examples to afford more insight. Most are trivial and contrived. What’s more, they present a finished outline.

That’s like “Yeah, ok, I get it. But… how do I get there?!”

In my decades-long quest to master outlining, I’ve only found one article that elucidated the process of outlining: “How to write a blog post outline” by Gail Marie on Animalz’s (a content marketing company) blog.

Gail Marie’s article ignited a few light bulbs for me.

But knowledge isn’t enough. Application — execution — is what matters.

And that still eluded me.

Not for a lack of trying or effort expended. I tried innumerable tips, strategies, and practices to make outlining an effective, productive habit.

Here are just a few.

• Brute forcing it
  Well, willpower doesn’t work. Benjamin Hardy could have told me. He did, he wrote the book on that. Came a bit late for me, but after I read it, I gave myself a break from self-flaggelation.

• Reframing

  It’s a great technique to change your thoughts to change how you feel about something, making it more likely that you’ll stay the course.

  Tried it umpteen times with every reason I could think of why outlining is a good, nay brilliant, idea.

  Didn’t work.

  The negative associations simply had more weight than the reframes.

  Not so surprising. Reframing doesn’t work if the new thought doesn’t engender sincere positive emotions. It stays in your head and doesn’t enter your heart, rendering it powerless within a few attempts.

• Visualizing

  I’d picture myself succeeding at creating an outline. I’d picture myself celebrating a freshly minted outline. I’d picture myself finishing an article in no time flat by having it write itself¹ from an outline I created earlier.

  I visualized my heart out, but it didn’t make a blind bit of difference.²

• Virtually all the tips available on creating habits

  Like chaining and starting small from B.J. Fogg’s Tiny Habits and never skip twice from James Clear’s Atomic Habits, to name just two that spring to mind without looking up my notes.

  It didn’t work.

  Not for outlining and not for any habit I wanted to establish.
  Not because the theory or the advice is wrong, but because they’re written by and for neurotypicals and don’t address a neurodivergent’s challenges with habits.

Whatever strategy or practice I picked, every time I sat down to create an outline with the unwavering resolve to “outlining first, write later”, my brain pulled a Houdini in one way or another. Even when following Gail Marie’s process for outlining.³

What foils me time and again (and this list is not exhaustive by any means!):

• I don’t do “should” or rather any “should” instantly surfaces my inner-rebel.⁴

• Outlines feel like a straightjacket. The one given me by my other side: my “you should stick with what you decided/said before”-side. It cramps my style. Puts the brakes on adjusting it — like the order, for example — to the flow of phrasing.

• As I’m outlining, particularly nice phrases uninvitedly pop into my mind. Or expressive words that clamor to be put in a sentence. It pulls me into phrasing, playing with words, like a delicious treat makes you salivate.

• FOL (Fear Of Losing) the phrasing or the words that popped up spontaneously makes me want to write them down and when I do, I struggle to resist tinkering with them.

• Writing things down helps me think through my argument. Mulling it over. Any holes in it stick out like sore thumbs that I just have to sooth. Which means changing and even abandoning any outline I managed to put together. (And that puts me in conflict with myself too, see straightjacket point above.)

• While I’m writing (or outlining for that matter), my brain coughs up anything and everything I’ve ever encountered that it thinks is related. It can make for interesting asides but more often than not it tempts me to rewrite whatever I already have because it offers a more interesting perspective.

• SPECing headings: adding pizzazz to heading by turning them into Surprising statements, giving them a bit of Personality (attitude), adding Emotion, or phrasing them to invoke Curiosity.

  It makes for wonderful subheads, but these obscure the points I want to make. (Which is exactly their point by the way: enticing visitors to stop scanning and start reading.)

  It feeds the obnoxious habit of my brain to spit out new angles every time I contemplate what I meant to say under a SPECed subhead.⁵

It had gotten to where I was despairing about the whole writing for a living thing — when it wouldn’t even have to provide all my income.

And it took the fun right out of writing.

Tinkering with words was no longer fun but a chore and one that made me berate myself for being so ineffective and unproductive, at that. Every article was taking so much time, I’d be earning less than a 16-year old flipping burgers at McDonalds.

No matter how much I love to write (and yes, I’d be doing it even if it weren’t making me money) there’s the inescapable fact that in a little over 4 years time, my income will drop significantly. Unless I find a way to supplement the state pension I’ll be getting (yep, I didn’t enough to save up for that, but hey, I had a great time, and reaching retirement age isn’t a given). It keeps you alive, but living is an entirely other matter.

So, I have to⁶ find a way to make writing for a living work for me within the constraints my health and my brain impose. And those are not just constraints on the hours I am able to work effectively and productively.

It’s either that or find another way to sustainably supplement that state pension. None of which appeal to me very much, if they even would be sustainable for me.

So I decided to take one other stab at making outlining work for me.

And to approach it as an experiment.

So that when I fell into one of my pitfalls again, I wouldn’t flagellate myself and despair, but could (and would) frame it as an opportunity to figure out what else I needed to tweak to fit my neurodivergent brain.

Find out how I finally unleashed the magic of outlining and started (!) unlocking the secret to making it work for me in the next installment of this two-part series.

I’m curious.
What felt like an awful chore and turned into an appreciated practice for you?
What triggered the change and how long did the transformation take?

Live long and prosper!

Marjan

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Footnotes

1. That’s what I was promised would happen by an outlining advocate.

2. Visualization supposedly helps to achieve your goals. Then again, it’s said to trick your brain into thinking it’s already done the necessary work.

3. Pulling it up just now to link to it, a pull quote caught my eye. I’d read it before. It didn’t sink in enough. Yet, it’s exactly what I did working on the piece where everything finally clicked. Not because I remembered it, but because I re-invented that wheel.

4. I’ve recently found out there’s a name for that: “demand avoidance”. [LINK NEEDED]

5. Adding a comment to indicate the actual point works sounds good to counter that. But it’s extra work. Not just to add the comment, but also to take them out again before publication (and I’m prone to forgetting to do that).

And then there’s my brain’s urge to adjust the comment to reflect what I’m actually writing when I get to that. Shouldn’t because that’s another slippery slope towards turning the piece into something else altogether.

The obvious answer is to SPEC after writing, right?

But SPECing often leads to the heading promising something the current text doesn’t quite deliver on… And then it’s a toss up between editing, rewriting, or killing the baby. The first two can lead to editing and rewriting other sections as well. The last one is painful to say the least. Ugh.

6. More fodder for my inner rebel.