Five Best Outlining Tools

Outlines are useful for more than just recalling painful memories of high-school research papers. This week we're taking a look at the five favourite outlining tools of Lifehacker readers.

Most of us received our earliest introduction to outlining by a teacher who insisted we needed to outline before writing papers and reports. While outlining is a solid tool for writing a research paper, it's also invaluable for writing other things—speeches, presentations, books, etc.—and for organising your thoughts into patterns that can be easily tweaked and edited before your reach the end product, be it book or business plan, is committed to its final form.

Note: The pricing for Microsoft Word and Microsoft OneNote is given for the standalone purchase price of the individual products. Both are available as part of the various Microsoft Office Suite configurations and are significantly cheaper when purchased as part of a suite.

Microsoft Word (Windows/Mac, Standalone: $134)

You certainly can't round up popular applications for outlining without Microsoft Word making an appearance. It wasn't conceived as an outlining tool but thanks to its presence on millions of personal and corporate computers the outlining tools built into it have seen an enormous amount of use. Outlining directly in document is a bit kludgy, but thankfully Word has an "Outlining View"—seen in the screenshot above—which makes outline creation and editing much easier. If you've never used Word to outline before, check out this tutorial to get started.

OmniOutliner (Mac, Standard: $US39.95, Professional $US69.95)

OmniOutliner is a comprehensive outlining tool for OS X with a host of features that make outlining more exciting and effective than simply scrawling roman numerals on a legal pad. With OmniOutliner you can not only create outlines but create additional columns of for input and data. Want your outline to have a column where you can check things off like a checklist or assign due dates? You can add it in. OmniOutliner has full AppleScript support so you script in tasks like having OmniOutliner put things on your calendar. Even if you're not looking for the more advanced bells and whistles like script support or multiple columns, the basic outline is still well designed. Inline notes allow you to add information directly to an entry in the outline for later reference but hide it when you want to look at just the outline. The professional version adds in new features like being able to navigate your outline by section, text clipping to pull in information from other apps on your computer, and audio capture to take voice notes.

Microsoft OneNote (Windows, Standalone: $80)

OneNote is a note taking and organisation tool that many Lifehacker readers have called Microsoft's best product. It's versatile—it's made appearances here, in the best note-taking tools and journaling Hive Fives—and the outlining functionality is well integrated and easy to use. One of the strong points of outlining in OneNote is the way outlines support the same drag and drop rearranging found throughout OneNote. Almost every single element in a OneNote page can be dragged, dropped, or easily manipulated with a context menu—the screenshot above shows an element in the outline right before being dragged into a new slot. Note: If you're curious about the GTD context in the screenshot, read our guide to getting things done with Microsoft OneNote.

Org-Mode (Windows/Mac/Linux, Free)

Org-Mode is a portable and open-source tool that runs off of the also free and open-source Emacs platform—Emacs is available for Windows, Mac, Linux and more here. You work on Org-Mode in a command prompt-like window and do all your editing and changes via the command line and keyboard shortcuts. It's definitely not the kind of application you toss at your computer-illiterate relatives but it is a powerful and flexible tool for organising outlines and more. The authors of org-mode maintain a large list of tutorials and screencasts for showing what can be done with Org-Mode, this one about using Org-Mode for outlining is of particular interest to today's Hive Five.

FreeMind (Windows/Mac/Linux, Free)

Traditionally one thinks of outlines as a linear progression down the page. Many Lifehacker readers however opted to outline their projects and ideas in mind-mapping applications like the popular and open-source FreeMind. You still get a hierarchical structure, headers, sub-headers, and so on, but the information is presented in a mind-map format instead of a simple list. FreeMind is very keyboard friendly, it's possible to create your entire outline without your hands leaving the keyboard. You use customise item flagging, colour coding, and more. FreeMind also made an appearance in and won the Hive Five for best mind-mapping tools.

Honorary mentions this week go to pen and paper—the timeless classic—and Mindjet MindManager, another mind-mapping tool repurposed as an outliner. Have an outlining tip, trick, or favourite application? Let's hear about it in the comments.


    Apple's newest version of Pages has added an outline mode that looks pretty decent:

    I own OmniOutliner Pro and have tried to use it in combination with an earlier version of Pages but found the fiddling with styles when moving from OO to Pages too time consuming so gave up. With this feature now in Pages I'm curious whether other users of OO are looking at Pages as an alternative?

    I prefer my outlining to be plain text. Having to tweak styles and formatting when my aim is to get down ideas and organise them is just too distracting. As a result I think my favourite outliner is an editor like Vim. It has quick indention, block folding, etc.

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