Writing Workshop Part 3: the Outline

Time for part 3! If you’re not familiar with this workshop, read the overview first. In this part, we’re going to turn your bullet list from Part 2 into a proper outline.

Once I have my list of “things I have to cover” in bullet-list form, I’m ready to create an outline.

I am serious about outlines. I do not regard them as a waste of time; indeed, one of the reasons I can be such a prolific writer is mainly because I outline so aggressively.

Take this “Writing Workshop” series. My original bullet list looked something like this:

  • Define your reader – start and end
  • Decide what you’re going to need to cover
  • Put things in order
  • Write to each outline heading
  • Double-check the checklist and revise
  • Reader is the “hero”
  • SLEEP ON THE OUTLINE before you write
  • Read aloud: does it sound like you?
  • One major point per ‘graf

Something like that. That’s not sequenced very well. The first five are in more or less the right order, but the idea of the “reader is the hero” is something I want to cover up front, because it plays into defining your starting and ending points for a piece.

The outline is where I can start to sequence this bullet list. I have some semi-firm rules I use for sequencing:

  • Do not cover a concept until you’re ready to put it into action. I abhor writing that expects me to memorize a bunch of arbitrary stuff before I even know why I care about it.
  • Similarly, do not go into a history lesson on something unless everything you’re covering is directly relevant to understanding whatever it is you’re writing about. If I want to write about gun control in the US, then at some point I need to explain why we have the 2nd amendment in the first place, but I don’t necessarily need to do that up front. I need to do it in a place where it will have maximum relevancy to the topic.
  • Do not foreshadow. I hate pieces that allude to something, and then say, “we’ll cover that later.” Now, this is a rule with a lot of variables. For example, if you sit me down in a car and start explaining how the brake works (which makes more sense than covering how the gas works s your first step), I might well inquire about the other pedal. It’s fine to say, “keep off that for now, we’ll get to it.” What’s not fine is to introduce the emergency brake, and then say, “oh, and there’s this cool thing called drifting – I’ll show you that later.” You’ve just distracted me and now I’m anxious.

If you look at Learn Windows PowerShell in a Month of Lunches, possibly the bestselling book I’ve ever written, you’ll see that each chapter delicately builds on what came before. Chapters don’t foreshadow things that are yet to come. In reading a chapter, you need only what was in the chapters before that in order to “keep up.” That sequencing, for a ~300 page book, took years to get right, but it’s why the book has been so successful.

So I might wind up with an outline like this:

  1. Define your reader – start and end
    1. Reader is the “hero”
    2. Who is your reader?
    3. Who will they be?
  2. Decide what you’re going to need to cover
    1. Simplest path between who your reader is, and who you want them to be
    2. Don’t worry a lot about sequence, but sequence if it’s obvious
  3. Put things in order
    1. Importance of sequence
    2. Outline sub-heads should be coverable in 2-4 paragraphs; if not, break it down to a further set of sub-heads
    3. SLEEP ON THE OUTLINE before you write
  4. Write to each outline heading
    1. One major point per ‘graf
    2. Write in a natural voice
  5. Double-check the checklist and revise
    1. Does the sequence feel smooth?
    2. Did you create any tangents?
    3. Read aloud: does it sound like you?

As you look at your outline, you should be able to think, “yeah, each of these sub-headings could be covered in 2-4 paragraphs.” If you can’t, then you need to break it down even further, with an additional (level 3) layer of sub-heads. I’ll go as far as 4 levels in an outline for a large piece. Because look: this is where all the work is. If you’ve got a detailed outline, writing 2-4 paragraphs for each heading is pretty easy. The piece starts to write itself, once you’ve got a clean, detailed outline.

Once you feel pretty comfortable with the outline, figure out which bit your’e going to write the next day. For a short piece, maybe that’s the whole thing. Before you go to bed, review the outline for what you plan to write the next day, and then go to sleep. Let your brain work on it overnight, and you’ll find that you’re more prepared to wake up and write about it, with less pain, in the morning.


As you might expect, you need to turn your bullet list from the previous assignment into an outline, using the tips I’ve shared here. Again, I’m happy to review and offer feedback until the end of 2019, if you’d like to post your outline’s URL here.

One thought on “Writing Workshop Part 3: the Outline

Comments are closed