Raise your hand if you enjoy outlining. Is your hand up? No? I used to be right there with you. I would dread the days in high-school writing courses when the teacher would be all happy-happy-joy-joy over an outlining assignment. Today though, my feelings are 180-degrees opposite.

Reasons for Outlining

Outlines are the scaffolding into which you create content. Outlines provide a plan and free you from the need to constantly step back and rethink what’s next. They make writing easier by letting you put your mind into writing mode and grind out your planned content one chunk at a time.

Any builder who is creating a new house works from a blueprint. Can you imagine the chaos if a builder showed up on an empty lot with no plan in mind, but rather just an idea that some sort of house should be put there? And that the builder and crew would work out the rooms and their layout ad-hoc as they went along?

Builders want blueprints so they can arrange needed parts and people ahead of time, and then execute against the plan. Outlines are blueprints for authors. Plan first. Then execute.

Top-Down Approach

The top-down approach is what I was taught in high-school. Start with a topic and break it stepwise into smaller and smaller chunks. It’s a reasonable approach if you are familiar with your planned topic and already have a story arc in mind for it.

Some years back I wrote a proposal for a book on building a bicycle as an example for aspiring authors. I build bicycles from the frame up so often that I lose count, so the following activities came easily to mind as the main arc for the book:

• Getting Started (tools, work area, supplies)
• Choosing the Frame and Parts
• Bolting Together the Initial Build
• Adjustments (derailleur, brakes, seat, controls)

These high-level activities became parts of the book. Then I broke each part into a series of chapters. For example, my favored build sequence leads directly to the specific chapters in Part III on bolting everything together:

• Part III: Bolting Everything Together
  • Chapter 9: Seatpost & Crankset
  • Chapter 10: Fork Preparation
  • Chapter 11: Headset, Fork, Stem
  • Chapter 12: Wheels and Tires
  • Chapter 13: Bars and Brakes
  • Chapter 14: Derailleurs and Controls
  • Chapter 15: Cabling

Then it took a bit more thinking on my part to sequence the steps in each chapter. Here’s what I came up with as the guiding sequence for Chapter 14:

• Chapter 14: Derailleurs and Controls (10 pages)
  • • 1) Bolt on the Rear Derailleur
    • 2) Mount the Front Derailleur
    • 3) Add the Chain
  • 4) Slip on the Grips
  • 5) Test for Trouble

Now it did take some time to work through the entire outline. I remember spending the better part of my Thanksgiving and Christmas holidays on it the year that I wrote it. The top-down approach worked though because I was capturing a sequence of steps that I was already practiced in performing.

Bottom-Up Approach

What about when you don’t know the story arc? There’s a bottom-up approach that has helped me when I lack clarity on organizing my content, but I at least know the details of what I want to convey. This approach has roots in my second-ever book, on Oracle SQL*Plus. I had a bunch of topics I knew I wanted to cover, and I was frustrated that I could not think clearly about an outline.

My solution? Sticky notes!

I may have begun with 3×5 cards, but I went to sticky notes due to having more wall space than table space. What I did was to buy a few stacks of sticky notes, and I wrote every single item that I wanted to cover in my book onto a separate note. The result was well over a hundred notes, and I just stuck them all over my wall randomly as the ideas occurred.

Then I spent several hours – maybe it was an evening or two – rearranging the notes into clusters of what I felt were related topics that could go together into the same chapter. This took some doing, because I had to think about keeping my chapter sizes even, and some topics seemed to fit into more than one cluster. But I kept at it and kept moving things around, and my thinking gelled and I ended up with a set of clusters that I felt good about.

These clusters became my chapters. I did have to think about appropriate chapter titles. For some chapters coming up with a title was easy, but others required some effort before I hit upon a title that encompassed the topics in the corresponding cluster. Then, for the most part, the sticky-note topics became the main headings, and sometimes the subheadings.

Iterating

Sometimes a certain amount of iteration is needed. Sometimes the iterating can change what you plan to cover. I went through at least four evolutions in outline for just this one article, and my message changed somewhat from what I had originally thought to say.

My original goal for the piece you are reading now can be summed up as:

• Explain my bottom-up approach

That goal led to this outline:

• Title: Bottom-Up Outlining
  • Top-Down Approach
  • Bottom-Up Approach

Realizing that my title did not quite match my planned content, I adjusted the title:

• Title: Do You Hate Outlining?
  • Top-Down Approach
  • Bottom-Up Approach

Then I realized I should say something about why outlining is even needed in the first place. I also wanted to segue into next month’s topic. Those two thoughts led to two more sections:

• Title: Do You Hate Outlining?
  • Reasons for Outlining
  • Top-Down Approach
  • Bottom-Up Approach
  • Setting Your Depth

My final change was an “in flight” change to add the section on iterating that you are reading now. Some adjustments as you go along are ok. You’ll have new ideas as you write, and your work in creating a good outline in the first place helps in integrating newly-thought-of content, and in deciding whether that content even belongs.

Setting Your Depth

How deeply do you go? How many heading levels, and how much detail? The answer is that you probably don’t need to go as deep as you first think, but do put enough depth and detail into your outline so that you can remember later what it was that you had in mind as your plan.

My first-ever book outline had main topics within a chapter, subtopics, and even the sub-subtopics were spelled out. That outline was too much, too deep, wasted too much time, and for the most part, only the main topics survived. The second-level, and especially the third-level topics ended up getting reinvented as I went along.

What works for me is to create a one- or two-paragraph description of each chapter in a book. Then I follow each description with a list of top-level headings that I plan for the chapter. Everything below those top-level headings gets worked out during the writing process.

Stay tuned! Because the writing process and how I chunk my way through a chapter is next month’s topic. I’ll give a hint though: I never write a chapter.