Outlines are an old-fashioned but very useful tool of writing. Unfortunately, they are nowadays somewhat out of fashion, replaced by “spontaneous writing”, encouraging writers to go with the flow rather than to follow a pre-defined structure. Though I practice and recommend “spontaneous writing” as a way to overcome “the writer’s block”, I have recently re-assessed the indispensable role of outlines in producing good writing.
Why do we need writing outlines? Because the old truth that we cannot simultaneously do something and decide what to do also applies to writing. Normally you cannot write and decide what to write about (not only in your text in general, but also in a particular section or paragraph). Outlines separate making hard choices about writing from writing itself. Thus, they enable free writing flow by placing hard constraints on this flow much like solid river banks define its meandering.
I usually prepare an outline for any substantial (i.e. more than a couple of paragraphs) piece of writing that requires any prior thought. For example, this post was outlined before it was actually written. Many learn this common sense approach already in high school. However, over the years I learned that this use of outlining is frustratingly inefficient, so much so that at one point I almost abandoned outlines altogether, considering them a waste of time. The problem is that initial outlines are rarely followed because writing normally assumes its own logic. Thus, I used to abandon the initial outline and never come back to it. The final text would barely resemble the outline: so why woud I bother to outline in the first place?
The book “Professors as writers” changed the way I view and use outlines. Nowadays I work with outlines throughout the writing process, not only at its initial stages. I prepare an initial outline, print it out (or display it on my second screen) and write the first draft, trying to follow the outline, but not religiously. After the first draft is written, I read it and come back to my outline in order to (a) change it to reflect what I’ve actually written and (b) improve the organization further (often through some serious shortening or shifting the pieces of text around). Thus, I end up with a second draft of the outline, which guides the second draft of the text. In some cases I even repeat this procedure one more time. Thus, to follow the three drafts rule outlines are needed not only for the first, “down” draft, but also for the second “up” draft.
I always discuss outlines with my co-authors. It is not uncommon for my students to hear that I can’t advise them on their early drafts before I see their outlines. Yet, make no mistake, outlines are necessary but not sufficient for good writing. My PhD advisor once told me: “I’m not a big fan of outlines. Bring me your writing!” He was right. Outlines are writers’ to-do lists. To-do lists are important but they are no substitute for the actual products. So make your to-do list and then do the work. Make your outline and then write.
The iterative process you describe is what best works for me, but I do recognize that outlines can be a bit frustrating. I also think that the importance of an outline is related to the type of document you’re trying to write. Outlining a scientific paper is hardly the same as outlining an essay.
And for this purpose, I have found Scrivener to be the best app. Maybe it is just me, but I hate to have the notion in my head that I am editing a single writing piece (document), like in Word, Mellel or for that matter, any typical word processor. Yes, one can set up an outline in Mellel and clicking on the heading takes you to your spot in the document, still the continuous flow of text bothers me. That is why I like the Scrivener approach, namely the cork board, the virtually separated subunits of a writing piece that will be rendered a single draft at the end of the writing process. I worked on my thesis in Scrivener until it reached around 40-50k words. I found it very useful when I was at a very early stage of jotting down and patching ideas. I then had to migrate everything to Mellel to handle subtleties required by a thesis. But since then Scrivener has evolved and has many more functions than in my time, so I guess one could write a thesis all the way to the end in Scrivener. Now there is support for citation software, footnotes whatnot.
Outlining in Scrivener works for me as well, but nowadays I often prefer to have a kind of a firewall between my outline and my text. So I do not change both of them at the same time. I either work on the text (supported by the outline), or on the outline (supported by the text). Scrivener is both a text and an outline so it sometimes leads to the same problem you describe for Mellel. Thus I almost always keep outlines in OmniOutliner (as I describe in the next post) and do writing in Byword (for shorter texts) or Scrivener (for longer texts).
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I agree with Aleh Cherp. Having just OmniOutliner for Phase 1 prevents me from digressing and from unnecessary distraction that may be more frequent in Scrivener.
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