Outlines in the writing process, part 1

Outlines are extremely useful for a writer.  But they are a limited tool.  

Recently, I got email from a philosopher with whom I’m working, which said, approximately (I’ve paraphrased a good deal): 

I’m having a hard time writing due to lack of formal organization of the theory and how the writing should reflect it, especially since recent changes in my plans, so I’m reworking my outline! Just started this today and it’s already taken me from frustrated to optimistic and excited about engaging these ideas. . . . My eventual goal is to establish a more detailed ToC before tackling the main content so that I can write with greater ease and efficiency instead of anxiously winging it.

What this writer expressed here reflects a general pattern that I have seen in other writers, and personally experienced, many times. It indicates the advantages of outlining—clarity of concepts and how to present them—and also hints at some of the problems: redoing an outline means changing plans that you laid earlier. In this post, I’m going to discuss outlines and the benefits and dangers of working with them.

Outlines are good

Outlines are excellent for trying to get a vision of the whole project, and having a vision of the whole project is really valuable for a writer: the better your sense of purpose for the whole, the easier it is to see the purpose of each part. And the easier it is to see the purpose of each part, the easier it is to write it effectively. If you see the large scale, then you can see how the pieces work together.  Without that large vision, it’s hard to write individual pieces that mesh with and support the rest of the work.  

Outlining is such a good tool for exploring that larger vision because it is something that can be done so easily: it only takes a few minutes to write down a sketchy outline of the main sections of a work.  A sketchy outline can be written and rewritten many times in the course of 15 minutes.  Admittedly, you can’t get into lots of details in a detail that you rewrite several times in 15 minutes, but, that’s just as well, in a way, because an outline’s help clarifying the larger vision and the flow of ideas is possibly the most valuable aspect of outlines. 

Outlines become multi-level hierarchies

In planning any large written work (at least of non-fiction), there is a pretty clear hierarchy of at least two levels that governs the work: there are the chapter divisions, and each chapter itself has some internal divisions (and the internal divisions might have internal divisions).  An overall outline of a work therefore, can be described with a detailed two-level outline along these lines:

Having a detailed outline like this is useful in that it gives a sense of the scope of overall work, and a road map to follow. However, while this much detail is good for a table of contents, it may not necessarily be good for a writer in the process of writing because I think the detail can be distracting, especially in the early drafts. If you’re trying to get an overall sense of some project, it’s easier if there aren’t too many parts to keep in mind.

Do one-level outlines

Instead of making a full, multi-level outline, I like to think in terms of working on multiple one-level outlines, each suited to and created for the piece of the project on which you’re working at the moment. You do a high-level main outline of the whole work, showing division into chapters and giving a clear sense of the work as a whole and how the chapters relate to each other. At a different time time, you work on the outline for a single chapter in which you look at the purpose of the chapter and you think about how each part contributes to the chapter’s purpose (which was earlier defined, of course, by the overall outline which identified the chapter’s place in the larger work).  Then, if you’re working on a major section of the chapter, you can do a one-level outline of the section to see its purpose and the main parts of the section.

This process of making different one-level outlines will produce a multi-level outline—as you nest each one-level outline, you generate a multi-level hierarchy. But it is psychologically different because your focus is generally turned towards the main purpose of the work (or the chapter, or section of the chapter) rather than to trying to manage all the details of the large work at once. Making one-level outlines, there are fewer distracting details, allowing greater focus on the sense of purpose for the main point of each section. Each new one-level outline is just a few pieces, which means they can all be kept in your head (short-term memory is commonly considered to hold about 5 to 7 items).

As you work with each one-level outline, you’re continually focusing on the main point (for either the whole work, or the part of the work), and the main sense of purpose, which should drive the work. This can help maintain motivation: when you get drowned in detail, in addition to the danger of being overwhelmed, there is the danger that the larger motivation is lost. Scholars who think of their work as too narrowly focused, or as too small/limited, often start doubting the value of their work, while those who see the larger purpose that motivated the work see value in it, even if it is highly specific in some way. This sense of motivation is true at all levels of detail: it’s motivating to see the sense of purpose of each piece of writing, so it’s valuable to work in a way so that every piece of writing is given purpose by its larger context.

Are detailed, multi-level outlines ever useful?

In this post so far, I have focused on how the attempt to produce a detailed outline can hinder writing, both by demanding an investment of energy, and by getting a writer bogged down in detail before the writing has even been done. (Well, that’s not quite fair: an outline is a form of writing, but it’s not a book or an essay, and for someone who is planning to write an essay or longer piece of narrative writing, an outline is not the goal.)  In order to start writing, you need a sense of direction, a few landmarks along the way, and willingness to start, but you don’t need a complete, detailed outline of chapter X unless you’re working on chapter X (and even then, a clear and strong sense of purpose is more important than a good detailed outline).

As a work develops and matures, a detailed outline can be very useful as a reflection of the current state of the text or a plan for revision. It’s an excellent tool for when you’re trying to review and revise a completed, or nearly completed whole.  It’s for later drafts and later in the process, when the issue is keeping myriad details in order, rather than early in the process, when the task is to get the big, important ideas into order.

Outlines and confidence

Early in the process a detailed outline can be a tool of avoidance and an expression of lack of confidence. If you’re not feeling sure of where you’re going, and you’re not feeling confident in your ability as a writer, an outline can feel like a great way of proceeding (“I’ll know where I’m going”), which it is until the outline becomes detailed enough to bog down the large-scale thinking.

Outlines don’t guarantee confidence, however.  An outline can provide a sense of direction and confidence, but the best, most detailed outline in the world won’t prevent self-doubt from creeping in.  Sometimes a detailed outline can cause doubt when a new insight suggests a different approach (and therefore a different structure/outline for the writing).  The more details an outline includes, the greater the chance for new insights to suggest an alternative—and, as long as you can learn, you’ll get new insights as you write. A sparse one-level outline, by contrast, offers space for improvisation and revision of details while retaining focus on the big issues and main arc of the narrative.  


Outlines can be helpful, but they can also provide a distraction.  My recommendation for writers near the beginning of writing—especially those who have not yet written a complete draft—is to stick to writing one-level outlines of parts of the work, allowing focus on how a few parts relate to a larger whole.  Don’t try to capture all the details in an early outline; do use a simple outline to help keep focused on the main purpose of your writing.

I had planned only a single post on outlines, but as I wrote, I kelp finding more that I wanted to say, so I’m going to follow this with a second post that discusses outlines further: it discusses some of the limits of outlines (which are linear and hierarchical, unlike the ideas a writer tries to express) and how to try to write about non-linear ideas.