[wrs]

Maybe I’m dating myself, but I was taught to start writing by coming up with an outline, which helps you organize your ideas into a coherent sequence. A list article basically makes its outline visible. The outline is also easily turned into an introduction that can address the non-list structure problem at the end of this article.

[bonestamp2]

Agreed. I've written thousands of articles and won a couple of writing awards. Productivity and quality really clicked for me when I started doing my outlines as lists.

I would do them in a text editor, one thought per line. The beauty of using a text editor is the shortcut keys that make it easy to move items up/down in the list. This is really nice as the outline develops and you build the plot and connecting tissue that ties the ideas together -- it's easy to play with different narratives in a text editor.

I showed this method to a friend who is a NYT best selling author. He doesn't know a lick of code, but uses a text editor in his process now too.

I actually do all of my writing in a text editor that doesn't have any spelling or grammar checking. This helps me stay focused on the ideas and think about editing later. My very last step of editing is moving the text into a word processor to catch spelling and grammatical errors that I may have missed.

Anyway, I share this in case anyone else finds it useful. If someone has a process that works really well for them, I'd love to hear about it too!

[justinlloyd]

Not thousands published for me, but hundreds published definitely. There isn't a modern software development trade or software industry magazine I haven't gotten a published article in to, in some form. And my article always starts as an outline of the subject I wish to talk about. One brief thought per line. Typed up in OneNote with any kind of spell check switched off, or a basic text editor like yourself, with no formatting or styling or care for grammar or punctuation or spelling. No annoying squiggly red lines to distract me from my train of thought. Short cut keys to move things around.

[evanmoran]

This sounds really helpful! Can you share an example or two with both the outline and then the final writing? I’d love to see how the ideas become the final manuscript.

[darkteflon]

That’s really interesting. I’ve recently been thrown into a role that requires lots of structured writing.

Could you elaborate on your process for outlining? What level of detail do you go into? Do you nest bullets or stick to one top-level list? Do you try to lay out the substance of your argument?

I’d be interested in reading anything you’d recommend on the subject, too. Always appreciate hearing from people who do this on the daily.

[bonestamp2]

> Could you elaborate on your process for outlining? What level of detail do you go into?

It depends on how developed the idea is. When I have give a lot of thought to something, especially the very moving and important points, I often know exactly how I want to phrase something poignant. In that case, I may write a full sentence, and if a great idea strikes me at this moment I might continue writing a full paragraph, but I ONLY do this if the inspiration is flowing and I don't want to lose it. Whenever possible, I will channel that flow into additional bullet points and work on the phrasing later.

> Do you nest bullets or stick to one top-level list?

I don't usually nest with formatting, unless the order of the sub points are really important; I usually list related ideas below each other. I do this because when I'm playing with the plot, sometimes I'll move those related points to come earlier in the story, even though they happened later in chronological time -- especially if I'm trying to pull in the reader during the first or second paragraph with something that is interesting, but is not an important event in the story.

> Do you try to lay out the substance of your argument?

The main points are usually the first items in the list and then I insert the connecting ideas and points in between. In terms of how substantive those list items are, I try to keep them short and stay high level in the brainstorming/outlining mode.

Other suggestions on process:

I delete a lot at the end. I scrub every word and phrase that isn't absolutely necessary.

The last paragraph I write is the first paragraph of the article/essay -- it's so much more natural to create a map of where you're going after you've already been there. This also takes the pressure off of getting started because you can start anywhere, and it makes writing the introductory paragraph so easy it feels like cheating.

The last thing I write is the title.

[hammock]

> Maybe I’m dating myself, but I was taught to start writing by coming up with an outline, which helps you organize your ideas into a coherent sequence. A list article basically makes its outline visible.

In that sense, listicles (as they are known) are a suboptimal/locally optimal solution to the lack of trust readers have, which was engendered by too much bad writing out there. Readers have learned to mistrust long articles that aren't obvious at a glance about the value they will provide.

[humanistbot]

Agreed. There are a lot of people in tech (and in university CS programs) who like to sneer at the humanities, English majors, liberal arts, and the like. This is basic essay writing that everyone should know.

[a9h74j]

Could "inverted pyramid" also apply to supplying technical "connective tissue"?

The traditional humanities teach appreciation of their own form of connective tissue, so to speak. Business writing arguably can be learned more quickly and emphasizes getting to the point.

[munchbunny]

What do you mean by traditional humanities? If you mean literature and skills like scripting out plots for characters and artful language in prose/poetry, then sure, it's not essential to business writing. However, if you're talking about essay writing, persuasive writing, clear language, laying out complex arguments, etc. then it's very, very relevant to business writing. Both categories are part of traditional humanities.

Getting to the point on nuanced issues like strategy or design is actually quite difficult because you have to both understand your point well enough to distill it and you have to be good at putting the words down. I'd argue that the "understanding" part is harder because, from my personal experience, someone who is thinking clearly and just not fluent in English still organizes the writing clearly, but someone who isn't thinking clearly will produce great syntax but the reasoning is hard to follow.

I see much more of the latter than the former in my day to day.

[mxuribe]

Same with me; I recall being taught to start things off with an outline, as you described. For work - where I get less chances to craft essays/long-form writing, it seems that lists prevail. It is more about "getting things done"/conveying actions/todos as fast/efficient as possible vs longer-form writing where there is opportunity to enjoy the "trip", or at least gradually dive into a particular topic. For me, essays - at least nowadays - are like slowly wading into the ocean deeper and deeper for enjoyment...While crafting lists is like taking a shower; a fast, practical way to get clean. ;-)

[tjr]

I enjoy Dave Winer's outlining tools. I'm not fond of the often-used Twitter authentication (just personal preference; no technical reason), but the overall concept and work flow of the tools themselves is really nice.

[gowld]

Are there current tools? http://outliners.scripting.com is stuff from the 1980s, last updated in 1999

Today's premium Mac offering is OmniOutliner ($20 barebones or $100 full-featured) https://www.omnigroup.com/omnioutliner/

[tjr]

Drummer is his current project:

http://scripting.com/2021/04/03/133021.html?title=theMakingO...

[antiframe]

Emacs has a wonderful outline mode and even more featurful org-mode. Easy to navigate, restructure, filter, etc.

[spccdt]

Here are a few outliners to consider:

* Workflowy * Roam Research * RemNote * Zavala

[PopAlongKid]

I receive his daily blog post via email, so I have read a lot of his comments about "outliners" and how wonderful they are. It always leaves me scratching my head; I mean, doesn't MS Word (and MS Excel, for that matter) have outlining capabilities built-in? How many different ways are there to construct an outline?

[gowld]

https://www.omnigroup.com/omnioutliner/features/

[runjake]

Link for others curious: https://www.google.com/search?q=dave+winer+outlining

If anyone has a better, more specific link, please reply, I'm curious.

[tjr]

http://docserver.scripting.com/drummer/about.opml

[LichenStone]

I tend to write in a very non-linear fashion, I'll often write individual sentences and paragraphs in a different order to the final product, as I think of them. Then I fill in the gaps, move things around until the writing forms a linear grammatical representation of the pure thought structure of the idea that existed in my brain.

[novosel]

I agree with you. That is also my personal mode of operation. I see the value in the outline approach, but it is, in my opinion, limited to a certain kind of writing. Where the work of thinking about the subject is already there. But there is also times when writing IS the thinking. There is a work being done when writing, not simply reporting.

And, I also think this is not an either_or situation, text can be locally structured by outline method, and then at other places marked by nonlinear growth, or progressing by lists. And these domains can overlap, and be of different sizes. Nor do I think there are only these three methods. Text can accommodate vastly different approaches.

[codyb]

Outlines are fantastic! I generally do a map of ideas I’d like to touch on, then organize into a sequential list which flows well, then expand out into a document.

[spccdt]

What tool(s) do you use to do that?

[codyb]

Either pencil and paper or ViM... things with buttons never go well for me! :-)