Rediscovering Outlines As a Productivity Tool


Through high school and college, I used to rail against having to use outlines because I saw them as stifling my creativity. It wasn’t until years later, as more of my own consulting work grew past just straight up technical writing of user documentation, that I rediscovered outlines as a productivity tool, enabling me to quickly make plans, organize ideas and structure information. Now I consider them an important part of my project planning arsenal.

How I Got My Outlines Back

I rediscovered outlines quite by accident. It happened when I first upgraded to a MacBook Pro (s aapl) and took a trial version of Omni Outliner for a spin. I was trying to think through a process for a policies document I was writing at the time, and as I played with Omni Outliner I found the old animosity I found towards outlines begin to melt.

The first thing I did was to set outline standards that worked for me and weren’t drawn from some composition textbook. I use two styles of outlines:

  • “Formal style” for when the outline may have to be reviewed by a client. I want them to be able to cite discussion points by number or letter.
  • “Brain dump style” is for outlines that are just for me. This style has a lot of bullet points and levels of indentation to organize the information.

Here is a sampling of the outlines I’m using now:

Yearly review/planning for next year. At the end of every year, I do a brain dump of what worked and didn’t work for me during the year as part of my own lessons learned exercise. My 2009 review is going into a series of outlines because they’ll offer me an easy reference when I look back to see if I am really applying any of the lessons I learned.

Stress management. As was true of many people, the down economy made 2009 a very stressful time for me both personally and professionally. One of the ways I try to alleviate stress when it gets bad is to write down the things that are causing me stress. For some reason, seeing them written down helps me to deal with them better.

Process planning. My day gig as a technical writer and all-around geek for hire often has me working with processes for various clients. While I usually reach for Visio or OmniGraffle, sometimes I like to see how the process breaks down in print. The outline I create then goes onto feed either the diagram I create or the accompanying text I write about the process.

Checklists. Being a technical writer and working in the IT industry means writing a lot of policies and procedures. I’ve come to count on outlining as a starting point for the checklists my technical documentation often require.

Outlining Tools I Use

While I spend my fair share of time in Microsoft Word (s msft), I usually try to avoid its outlining tools because I find them cumbersome. Typically when creating outlines I use a moleskine notebook, yellow legal pad, OmniOutliner Professional or CarbonFin Outliner. I count OmniOutliner Pro as my favorite because of its flexibility and multiple export options. Outline tools now work for me, as opposed to me working for them (as in a classroom assignment).

Do you use outlines as productivity and planning tools?



I came to this post via the link from James Fallow’s blog entry on outliners. Reading this post and comments, I now realize what I’ve been looking for in a list app for my iPhone is very similar in function and visual layout to these outliners discussed here. Can anyone recommend a good mobile app they’ve used for this purpose. I just want something simple, fast, efficient, and flexible that can create checklists with sublists/subitems. That perfect app for your mobile device to dump your thoughts in a semi-organized fashion and be able to copy/move/edit/refine/restructure/expand as needed. I’ve tried OmniFocus, Things, and just about all the List and GTD apps that are out there and find most of them too cumbersome with their emphasis on GTD integration. The only one I have really liked is Lists (free version with ads or $.99 without) by Mobilityware because it’s simple, clean, and most importantly let’s you create sublists. The only other List app I’ve seen that has sublists or nested lists is List Monger, which I have yet to try. I would appreciate any suggestions. Thanks!

Owen Marcus

I use FreeMind as my free mindmaping program then convert it to an outline in Word. It is a lot easier to have a mindmap to dump ideas into over a week of letting my thoughts congeal then written copy. As mentioned above, I can easily move around my thoughts and create branches to fill them out.

I don’t always use everything, but it I have an organized list to choose the best from.

Vishu Ramanathan

Great point about how tools like Word that are not designed to be outliners tend to have cumbersome outline views.

If you don’t have a free version of Omni Outliner, check out It’s web-based so you don’t have to install anything, but it still feels great in your hands.

I also came back to outlines as a consultant. They are a great way to organize and exchange information with clients. That’s why collaborating online on an outline is much more interesting and effective than collaborating online on a document.

Hobie Swan

I wrote a book using mind mapping and it really blew me away. Maps (and, I suppose, many other kinds of outliners) worked so well because, while I didn’t really make the connection as I was doing it, they were chunking my text. I was just sending out branches, then addint notes to each branch as a way to capture my ideas. But then I realized that I shift the branches around, export to Word, and see which flowed better. I still had to do a lot of writing to knit it all together. But it gave me a freedom I hadn’t experienced before. So I’m all for outlines–especially when you can build them out like this and make them sort of super outlines.


Thank you, Will. That annual planning and review is an idea worth stealing, er, re-using. Mind mapping and the Omni Outliner help info both gave me new perspectives on productive uses of outlines.

Outlining became really powerful to me when I found how to use the pages tree view in Atlassian’s Confluence wiki. So easy I do not like to use Word any more. In a collaboration setting, wiki pages and text are well re-usable and much more suited than attachments to get consensus based results and continual improvement.

Wish you a great 2010 and many check marks on your outlines.


If I ever have to write something more than a page or so I usually start with Word’s outline mode since the items then become your headings and have the correct size depending on their tab level.


OmniOutliner is an indispensable tool for me. There are certain kind of people that just think in bullets. Concise. Organized. To the point.

You should try OmniFocus, which is a bit like the Outliner, but geared towards task management and GTD.

Paul Jacobson

I’m with you on that. I also have Circus Ponies’ Notebook which is a more developed notebook app and better for a lot of my work than OmniOutliner but I find myself returning to OmniOutliner again and again for its simple design and powerful features.

OmniFocus is by far my best productivity app and I have days when I wish I could really simplify my workflows and do everything in Omni-apps.


That’s funny because I used to HATE outlines too. I used to think that algebra was so useless but I have to admit, I’ve used it a few times in real life. Who woulda thought?

Buzz Bruggeman

I find that creating MindMaps in Mindmanger from, and then export the maps to Outline form works great too!

Also, it is much easier, to manipulate outline objects in MindManager. Also, I have found myself driving my presentations from MindManager rather than PowerPoint, and I would never consider driving a presentation from an outline.

George Entenman

If you ever have to write an old-fashioned style essay – you know, a bunch of paragraphs with no bullet points, diagrams, etc. – I find it useful to start writing and then use the outliner to structure what I’ve written. It actually helps you find out what you think, kind of like mind-mappers, etc.

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