There Are No Shortcuts (or the Case for Outlines)

Photo by Hanna Morris on Unsplash

Here's something I've said to many of the people who ask me for writing advice: "You're not going to like this, but the solution is to outline."

Almost no one likes outlining. Drafting can feel like magic: insights and eloquent turns of phrase come out of nowhere. Same with editing. Though there can be painful moments where you have to re-organize an entire article or book, you can still get lost in taking raw material and transforming it into something beautiful.

But outlining? It's hard, time-consuming, and at the end you still have to figure out a way to translate it into a draft.

And yet outlines are magic. They can solve nearly every writing problem. And there are many writing problems that can't be solved any other way.

Let me give just one non-obvious example.

What the hell did I say?

Yesterday I got an email from one of my clients, Mark Moses, that said in part:

I just wanted to tell you that the advice to reverse outline the book was golden. I wouldn't have known what to do with such advice last fall, but it has really helped me work through the chapters. I am more productive now than at any time last year.

Mark and I had been doing a late-stage edit on the draft of his book (which I will definitely be telling you more about once it's released because it's really damn good) and although we were pretty happy with the general structure of the book, we both had the sense it wasn't going to be effortless for the reader to follow his argument.

So of course I told him, "You're not going to like this, but the solution is to outline."

Typically, we outline before we draft. We start with a single sentence statement of the theme, then we break that theme down into 3-8 points, and if necessary we break those points down into 3-8 subpoints, and so on.

But you can also reverse outline something you've already written. This is a tactic I learned from Keith Lockitch at the Objectivist Academic Center. You take your draft and instead of breaking it down you condense it. Each paragraph gets condensed into a single sentence. Then each section gets condensed into a single sentence. You keep going until you reach a full condensation--a statement of the theme.

If a traditional outline is a blueprint, a reverse outline is an x-ray. It allows you to see the structure of your piece in its essentials and assess the logic of the argument.

And here's the key point: there's no other way to do it. There's no shortcut for ensuring that you've said what you want to say as well as you can say it.

Is it fun? Not really. Though, as Mark later told me, "I have 'enjoyed' doing the outlines more as I have gained proficiency."

I totally agree with this. I don't think I'll ever love outlining or reverse outlining. But funny thing. The better I got at it, the less I disliked it.

A few words on reverse outlining

The biggest mistake people make when doing their reverse outlines is writing down what they intended to write or what they wish they had written. But the whole value is condensing what's actually on the page.

Really important: you need to formulate each point as a complete, grammatical sentence using the same key terminology you used in your draft. 

Here's why that matters. I was editing a piece today and couldn't figure out why a section felt confusing. Then I realized: the main issue I was talking about in the piece was innovation, but at a certain point I went into the wider phenomenon of progress and basically forgot to go back to innovation.

The two ideas are so closely related that if I had been reverse outlining carelessly the switch might not have been apparent. But the reader would have noticed it--not consciously, necessarily, but he would feel lost, confused, unsatisfied.

A few words on judging an outline

How do you know when your outline is good? I can't give you a recipe, but what I recommend is what I call the paragraph test.

Get rid of the bullet points and format your outline so that it looks like a single 3-8 sentence paragraph. A good outline should read like a well-written paragraph. You should be able to hand it to someone and have them know exactly what you're arguing.

If your outline doesn't make for a good paragraph, that likely means (a) you're using insanely complex sentences that are trying to squeeze multiple thoughts into a single point, (b) you're missing a key point, and/or (c) your transitions aren't clear, i.e., the relationship between your points isn't fully logical.

(By the way, you can actually write your outline this way. Instead of writing your outline in bullet point form, write it as a paragraph and then break it up.)

Final thoughts

Outlining isn't a duty. It's a tool. If you can crank out perfection off the top of your head, by all means go right ahead and skip the outline. But if you can't, there's no more powerful tool to have in your arsenal.