In the first of this pair of posts, I discussed how detailed outlines can lead to distractions, and argued for using simple outlines to help guide the writing process. In this post, I want to follow up with some thoughts on some of the reasons outlines can lead into difficulty, especially related to the way that outlines promise clarity and direction that they do not entirely deliver, as well as to discuss ways of dealing with these problems.
Ideas are neither linear nor hierarchical
The biggest problem with outlines (and, indeed, expository writing more generally), from a theoretical perspective, is that many or most ideas are not linear or hierarchical, and outlines are necessarily both. Some ideas and/or aspects of ideas are linear and/or hierarchical, but plenty of ideas are connected interdependently: they cannot meaningfully be explained or understood outside a context of related ideas.
For the writer, constrained to linear discussion, this can be a tremendous difficulty. It’s common that one aspect of a large theory cannot be explained meaningfully without also explaining one or more other aspects of that same theory, which makes it very hard to start: each possible starting place is problematic because it cannot be understood without other related ideas, none of which obviously comes first or stands outside the larger structure of reasoning. In such a situation, there is no clear starting place. If describing A requires describing B, and describing B requires describing A, where do you start?
For a written work, there must be a starting place. That starting place may be an imperfect compromise, but as a matter of practice, compromises are necessary despite being frustrating and difficult. Difficulty accepting such compromises leads to the common problem of rewriting the outline, and starting a new, “better” draft, which usually delays completing a work.
Competing outlines and the limits of vision
I have been emphasizing the importance of having a vision of the larger purpose and arc of the presentation, and to settle on a basic, overall outline. But, as I have argued, no outline will be perfect, and the more detail included, the greater the chance of seeing weaknesses in the outline, and therefore thinking that some other outline will be better.
A writer, starting with a new outline, often begins with a sense of confidence—a sense that the outline will do a good job of guiding them through the writing, as well as a good job in presenting the ideas to future readers. The confidence provides invaluable motivation for pressing ahead: it’s hard to keep working if you don’t have some hope for what you can accomplish.
Inevitably, the writer reaches a moment where it’s necessary to negotiate the problems built in to the current outline due to prior compromises (or when unanticipated problems arise). At such moments, it often becomes tempting to consider a new, different outline: “If I had ordered it differently,” the writer thinks, “I wouldn’t have the problems I’m negotiating now.” This is true but it omits the reality that they would be exchanging one set of problems for another: the new outline will have problems, too.
Outlines are like many other plans or expectations: they seem great when you start out, but along the way, you discover difficulties that you had not anticipated. Both for finishing each individual project more quickly, and for building skill as a writer, it’s valuable to stick with flawed outlines and figure out how to negotiate the problems.
Resolving outline difficulties: finish a complete draft before rewriting
A writer must learn the skill of managing the problems within an outline: instead of starting anew and discarding a partial draft to adopt a different structure, the writer wants to finish drafts and projects. There may be cases in which rewriting with a new structure is absolutely worth the effort, but until you’re regularly completing drafts of different projects, try to stick with one outline for a complete draft before switching. The experience gained in finishing an imperfect draft is so valuable that temptation to change an outline should be resisted before a draft is complete. This is not a strict rule but rather a guiding principle. Basically, you don’t want to start rewriting stuff you’ve already written before you’ve completed a draft. If you’re working on a first draft of the introduction and you decide to swap the order of chapters, that’s ok, because it doesn’t require re-writing. If you’re on your first day of writing, you can change the outline all you want, with little loss (though at some point, you have to commit and stop debating alternatives). But if you’ve written two chapters, and decide that a different organization would be better, and that requires scrapping the two chapters you’ve already written? That’s can be a huge danger for less productive writers. If you’re pumping out a book and three articles a year, and you think rewriting is the way to go, then trust your experience. If you’re struggling to finish one project, then stick with one outline until you complete a draft.
If you think a complete revision of structure is worth the effort, consider the possibility of having two separate projects, one that reflects your original views, and one that details your developments. You would not be the first scholar to publish work that they would later replace or reject.
It’s necessary to find the right balance between holding on to old drafts and old structures and willingness to rewrite. Generally, it’s valuable for writers to be willing to rewrite, to feel relaxed and confident in their ability to produce new work, and not to hold too tightly to old drafts that reflect old ideas. Writers should believe that creating a new draft isn’t too hard, and can be done in a reasonable time. But people who are having trouble finishing a complete draft, and who keep working on outlines, or constantly revising outlines, it’s important to finish a draft using one outline.
Resolving outline difficulties: writing
Part of the writer’s response to outline problems is finding the language to acknowledge and accommodate the weaknesses of the structure, by explaining how the structural issues relate to theoretical issues. A lot of this is done with simple phrases that imply the relationship between structure of text and structure of ideas. For example, the reader can be referred to a different part of the work: “This will be discussed further in chapter/section x,” or “as previously discussed in chapter y.” Explicit efforts to show a reader how parts of a manuscript relate will also help the reader understand how the work as a whole holds together. Telling a reader “the discussion branches here, and we will discuss the other branch(es) later,” is not only a statement about the text, but also, implicitly, an indication about the relationship among the ideas that you’re trying to discuss. Showing that you, the writer, made a choice to proceed in one way, implies that the ideas are not ordered even though the manuscript presents them in an order. It is a nod to the alternate outlines that could have structured the work.
Write more than you outline
Once you have a general sense of where you’re going and a rough one-level outline, it’s time to write sentences and paragraphs and try to make that into a coherent flow. In that effort, you will learn a good deal about your project. Early in a project, armed with a rough outline, you start to make notes toward that outline. Ideally that writing will manifest as flowing prose, but even if it’s just fragmentary notes, it’s a good start; it will help move the project forward more than another run through an outline. Outlining is a useful tool, but it doesn’t produce essays, articles, or books. Nor does it produce as deep insight as trying to explain a coherent argument in writing. You can learn a lot about a project by outlining details, but you learn more by writing.