Ideas Live and Breed in OmniOutliner

OmniOutliner provides a flexible and powerful workspace for performing a wide range of information processing tasks – from organizing a complex project to planning a best-selling novel. Heck, you can even create a shopping list with the program!

Combining power options with ease of use, OmniOutliner may be the best true outliner available. On any operating system. In today’s review, we’re going to take an in-depth look at what you should expect from a fantastic outlining application, and how OmniOutliner stacks up against the competition.

An Outliner by Any Other Name

Before beginning my review it will be helpful if I define just what I mean when I use the term “outliner.”

Everyone knows what an outline is, but there is some disagreement about what is appropriately called outlining software. For some, an outliner is any application that allows you to collect and organize free form information in a hierarchical structure. But just as I would not call every application that provides space for writing notes a word processor, I prefer to narrow the definition of outliner to those applications which focus my work on the outline itself. Give me one main window containing the outline, and this is where I will do most of my work.

For example, a terrific application like MacJournal allows you to structure your documents in a hierarchy, but your focus will be almost entirely on the editor window. MacJournal is not an outliner.

Another attribute of a true outliner is that any item (whether you call it a note, topic, or heading) can be the parent of sub-items. Going back to the MacJournal example, you can only build hierarchy with folders. The articles themselves cannot be parents of other articles. Most true outliners don’t even use the concept of a folder in the outline.

To be sure, most of the applications in this class fall somewhere along a spectrum. Outlines of a sort can be created in most of them. Nevertheless, I’m drawing this distinction because the criteria I will use to evaluate OminOutliner are not the same as I would use when discussing DevonThink or EagleFiler, for instance.

Two Flavors

OmniOutliner is just one of the applications developed by OmniGroup, a software company that has been around for over 20 years. OmniOutliner comes in two editions, standard and professional. Standard costs $39.95 and has all the features most people will need in an outliner. The professional version is $69.95 and adds some handy features for power uses. I’ll describe some of these below. You can also buy a family license. The 14-day free trial period is a little chintzy, but you should be able to put the application through its paces and get a feel for how well it works for you in that time.

Installation is familiar for anyone who has used a Mac for any length of time: download and mount the disk; drag the application to the application folder; get started.

OmniOutliner Welcome

OmniOutliner Welcome

This Welcome Screen opens the first time you run OmniOutliner. Believe it or not, this is a OmniOutliner outline, which demonstrates some of the versatility of this application.

Head Space

Describing what you can do with OmniOutliner is a little like describing where you can go with a car. It all depends on what destination you have in mind. Essentially, it is a workspace for collecting information, but unlike one of the applications mentioned above, most of the information you put into OmniOutliner will probably come from your head. Do you need to plan an advertising campaign? Design a college course? Write an owner’s manual? Manage a work schedule? Organize a meeting? You name it. If you can break the information down into small pieces, you can manage it with OmniOutliner.

OmniOutliner includes three features, rare in other outliners, that help provide the power to do these tasks.

Key Features

1. Customizable Columns

With OmniOutliner you can add customizable meta-data fields to your information viewable in columns right in the outline. This is a crucial feature if you are going to keep your focus on the main window. For example, if you are creating a project outline, you can use meta-data to indicate which members of your team are responsible for implementing which tasks. Include due dates and priorities. Add a budget column.

Having this information directly in the outline pane makes it instantly visible and comparable. You can see if one task that is dependent on another has an impossible due date.

OmniOutliner is one of the rare applications not a true database that allows you to create your own fields in this way. And you can choose from several different column types (set through the column inspector): rich text, pop-up list that you define, date, duration, check box, and number. You can even optionally total a column of numbers, which is, to my knowledge, unique among outliners. You can sort the information in these columns, either throughout the entire outline or subsets of it.

Think of OmniOutliner as combining the advantages of an outline with those of a table or spreadsheet.

2. Inline Text

Most outliners provide the ability to create extensive rich-text notes associated with each item, but few provide the option of seeing those notes in context in the the outline, an essential feature if you are composing long documents, and very useful for other purposes. Outlines by definition break information into bite-sized chunks, but good writing requires pulling those chunks together into a comprehensible and coherent whole. Inline text is far more compatible with creating clear writing than viewing each chunk individually in its own window. With inline text notes, you can see at a glance if the preceding paragraph flows smoothly into the the one you are currently working on. In short, inline text provides a more “word processor” like experience.

OmniOutliner is one of the few outlining applications on any platform that incorporates inline text. By itself, this feature sets OmniOutliner above most of the competition. You can, optionally, view notes in a separate window, if that works best for you.

The screen shot below captures a hypothetical meeting I’m planning. Note that I’ve added two columns, one for the person responsible for each topic at the meeting, and one for the time I’m allotting for each. Also, the red text are inline notes. These are short notes, but they can be much longer if necessary.

Sample Outline 1

Sample Outline 1

3. Hoisting

The ability to zoom in on one single topic and its subtopics is called hoisting. With a hoist feature you can shift back and forth from a focused view on one topic to a broad overview. The more complex and extensive your outline, the more important is this feature.

OmniOutliner does hoisting very well, and the professional edition provides the Section Drawer, which allows you to navigate directly from one hoisted topic to another.

In the screen shot below, I’ve hoisted my meeting plan to the agenda so that I can focus on that during the meeting.

Sample Outline 2

Sample Outline 2

Not Cloning Around

One key outlining feature that OmniOutliner does not currently include is the ability to have one topic appear simultaneously under two or more headings – a feature commonly referred to as cloning (a similar concept to using aliases in the finder). Changes made in one location appear in all the clones. This is a useful feature in project outlines, for instance, where you might want to have a task appear under two different people who have responsibility for it; or in a writing project for which you may be unsure where you want to certain topic to appear.

Of the four features I’ve mentioned here so far, cloning is the one that is least important to me, so I don’t really miss it in OmniOutliner. However, some power outlining enthusiasts see this a gross omission. OmniGroup say they intend to add cloning in a future release, although it will not appear in the upcoming version 4.0 (intended for release by the end of the year).

Sprucing Up Your Information

When you create your outline in OmniOutliner, you can add any number of items and sub-items going down to virtually any level. Reveal arrows allow you to show or hide whatever level of detail you need.

The search feature is limited to the current open outline, but is robust and fast. With long, comprehensive outlines, it saves a lot of poking around time.

Through the Inspector Panel, OmniOutliner gives you a great deal of control over the look and feel of your outline. You can select to have the rows alternate background color, or switch on grid lines to help you visually navigate your data. You can choose to display a checkbox at the start of each item – fill up the check boxes in sub items and the top-level check box is automatically marked. You can select the numbering system you prefer, or turn off numbering altogether. You can change the text format item by item or use the extensive collection of styles tools to set the format on a level-to-level basis.

Outlines are not limited to text. You can add images, URLs, and – in the professional edition – voice recordings to your outline. You may have noticed the button-looking item in the first screen shot of my hypothetical meeting outline under the “Doug’s office downtown” heading. That’s an embedded screen shot of a Google map to the meeting location. Clicking on it reveals the image, like so:

Sample Outline 3

Sample Outline 3

Areas for Improvement

Creating new items quickly and putting them in their proper hierarchical order, and subsequently being able to quickly reorder the outline are crucial abilities for any outliner. Here OmniOutliner could use some work. Some of the keyboard shortcuts feel arbitrary to me, which is the same as saying I’ll never remember them. For example, the key combination of Shift-Command-] creates a sub-item, while Shift-Command-[ creates a parent item.

Moving items up and down the outliner with the keyboard requires using the appropriate arrow key in combination with the Control and Command keys, which is just plain silly since Command-Up Arrow and Command-Down Arrow don’t appear to do anything – why not save users the extra key stroke?

I’ll admit that these criticisms are a little nitpicking, especially since there are other ways to achieve the same results – drag and drop, for one. Still, the goal should be making the application transparent to the work at hand, and OmniOutliner does not quite achieve that goal as yet.

OmniOutliner can export to a wide range of file formats, but I’m disappointed in its inability to import or export comma separated value files, making it cumbersome to share data with a spreadsheet like Numbers. This is an especially odd omission given that OmniOutliner can import and export text files with tab separated values.

Sorting the Competition

The only outlining software I’m aware of that is more powerful than OmniOutliner is Neo (and its predecessor Tao). Neo is a full-featured, true outliner that does an even better job with inline text, plus it has cloning. However, it is much more complex and will take more determination to learn to use effectively. OmniOutliner is by far the better choice for novice outliners, and anyone who values ease of use.

If you don’t need a power outliner, but would like a handy list-builder, you might want to check out Opal. Developed by one of the people behind the popular Acta, an early outliner for Macs, Opal does not do columns or inline text, but handles nested lists with ease.

Circus Ponies Notebook and Aqua Minds Notetaker both have outlining as core functions. They are popular information managers, but when I want to outline, I need to focus and I can’t do so as effectively with the notebook metaphor these two applications use.

Put a Check in the Check Box

OmniOutliner is not the application I would choose to collect information from other sources. The professional edition does include a clipping service, so that you can drop text from other applications into your working outline. This is a handy feature, but is not robust enough to make OmniOutliner a proficient data storage option.

But OmniOutliner works extremely well when I want to turn my attention to one project at a time. It puts all the information I create about that project into a single window. Its combination of powerful, useful features is rare, and it is reasonably priced.

I’d give OmniOutliner a rating of 7 out of 10. Cloning, a more user-friendly collection of keyboard shortcuts, and a little more versatility with importing and exporting would elevate OmniOutliner to an almost perfect score.


OmniOutliner is an amazingly flexible program for creating, collecting, and organizing information. Use OmniOutliner's document structure to brainstorm new ideas, drill out specifics, and line up the steps needed to get everything done.