Do I need to write an outline?

I’ve had many conversations with writers about how to write essays, articles, and books. People often assume that they cannot start writing until they construct rigid outline. That’s a wrong assumption — most of the time.

I had an otherwise wonderful English teacher in high school who tried to teach the class to write well. Unfortunately, he had strong ideas about the process that did not mesh with mine.

We’d be assigned to read a book and write a book report. Fine. But the teacher insisted that we write an outline of the report; hand that in and get it approved; then write the essay based on the outline a week later.

It didn’t take long for me to find a workaround. I read the book. I wrote the essay. Then, working from the essay, I wrote down the outline based on the structure I’d ended up with. The teacher was so impressed at how well I kept to the outline!

I regularly got As in the class, so I suppose it worked out. But it wasn’t until I began writing professionally, 20 years later, that I realized his “write an outline” training was good for me. It made me pay attention to how I structured my own essays, and it helped me understand when I was ready to stop researching and begin writing.

Maybe a list, rather than an outline

Since I write nonfiction that is meant to explain things (“what happened” or “how to do this”), I have learned that it’s important to make a list of the points I want to impart, and to organize them with some kind of gradient that introduces each element but doesn’t confuse or overwhelm the reader. That can look a lot like an outline, at least to an outsider.

I do this for even simple essays, such an Amazon review. I write down the product’s advantages and disadvantages as bullet points, and then for each one, I explain why they matter. Then I take out the bullet points, add a summary paragraph… and I’m done.

Sometimes I don’t know those things ahead of time; I only find out what they are from the reporting or the research.

That’s why my work usually starts with a question to which I personally want to know the answer, such as “What makes an online conference work well? How can you ensure it doesn’t suck?” or “What resources can help women in technology?”

I collect answers to the questions. Then I make lists (I like lists, can you tell? …really, the “Schindler’s List” jokes are too obvious) that organize and summarize related answers. That helps me identify the important points to include. It helps me know what I have to say.

I almost always have more information than I have room for. That’s another reason to organize those thoughts into my list of “What do I want to make sure the reader understands?” Because if I want to emphasize A, B, and C, then I probably need to leave out, X, Y, and Z, which likely is a distraction from the points that matter.

Outlines are a guideline for yourself. You can change them

That list — or outline — helps me know what to leave out. If I go off on a tangent that doesn’t contribute to the points I identified as important, it means I should cut the text.

I do permit myself to write the tangent. Sometimes, doing so makes me realize that I’d left something out of the list and it needs to be included. It’s okay to add more points as I work, but I should be conscious of the choice I make. (Ironically, this paragraph is an example of the phenomenon.)

Still, I nearly always rearrange things as I get underway. For instance, the article I’m working on right now has two questions: “What are the criteria for the job-being-discussed (that is, the job requisition)? and What are the things the individual who gets this job needs to be prepared to work on?”

I started out assuming that I’d first discuss the former, but as I wrote I realized I needed to begin with the latter. No big deal. I can move them around.

The only thing that matters is that you find what works for you. Each of us is different!

There are exceptions

Sometimes, you need to create an outline because it matters to other people. That’s common when you write a white paper that a client needs to approve; someone else has their own idea about the things that matter and how they should be presented. If you write the white paper first, you’ll discover late in the process that the client thought the section on risk management should be addressed first, not at the end where you thought it was more appropriate. The rewrite makes everyone cranky.

Books genuinely do need outlines. There are so many things to say, and you want to track that you say them all. Even so, end result of the dozen-or-so books I’ve written didn’t look much like the initial outline.

But when I create an outline ahead of time, I use the same process. I write down an organized list of “things I want to be sure to say.” A client or book editor may change what’s included or the order in which I say them, but ultimately I’m still working from a list of Things I Want To Say.

Fiction and nonfiction are different

On the other hand, I write nonfiction. Novelists can work without any kind of outline, sometimes. As Anne Lamott wrote in Bird By Bird (one of my favorite books about writing), E L Doctorow started Ragtime with a vivid picture of a street scene in his head. And (I paraphrase) the author didn’t know where the road went, so he had to follow it and find out. Which probably is what led him to say, “Writing a novel is like driving a car at night. You can see only as far as your headlights, but you can make the whole trip that way.”