5 Outliner Apps for Mac Compared

Have you ever worked on a larger project and at some point wished that instead of a giant box of notes you had some shorter, more accessible overview of the entire thing? The run-down of a lecture series, the step-by-step process of realizing a website overhaul, the hierarchical overview of customer requests?

Whatever challenge you face, an outline can save the day. It allows you to quickly see a structure or find a detail which can get lost in regular notes. In this article, we’ll take a closer look at five outliner apps for Mac and their respective benefits and shortcomings. It is by no means an exhaustive list, but I’m sure it will get you started.

OmniOutliner – The Godfather of all Outliners

If OmniGroup makes an app, they get serious about it. Probably best known for their GTD app OmniFocus (which we have reviewed in detail here), they’ve also developed an outlining app which has a very exhaustive feature list.

The most basic feature of an outliner is of course a list; that’s all an outline is at its core. It gets interesting when you create nested lists (different levels of indentation) or want multiple columns to a list, with functions being performed dynamically.

OmniOutliner excels at that, even though the learning curve is rather steep for beginners. To ease you into the app, there are onscreen-help resources and the user manual to walk you through all the steps. Even better, though, are the included templates, which provide a hands on experience without you having to come up with something right away.

The app is much too complex to cover every feature, so here are the ones that stood out for me:

• Multiple Columns: OmniOuliner not only allows you to create simple or nested lists, it allows you to add columns to a list (reminiscent of Numbers/Excel). That’s especially useful for the representation of complex information, which can’t be forced into a single list.
• Mathematical Operations: You can perform basic spreadsheet functions. For example, calculate totals for your monthly budget proposal. That’s great if you don’t want the complexity of a full blown spreadsheet application but a quick list of your numbers.
• Individual Formatting: You can style the way your lists are displayed as well as the text within them. That allows for highlighting certain content to draw attention and help even more with structuring your notes (great for lecture notes in college). The text editing options could be more comfortable; there seem to be no real shortcuts and I had to resort to the templates to figure out how to accomplish what I wanted.
• Inline Notes: I found that in the meetings I attend I often create outlines that are too detailed because I can’t put all the information where I want them. With OmniOutliner, you can create a bullet point and then add an inline note to it. It’s a great way to keep your outline clean and still have all the relevant information at hand.
• Attachements: Have a photo, another document or a video that fits with the content of your outline? Simply drag them into the app. They can be appended to any bullet point, be their own bullet point or even go into inline notes. It’s a great way to keep all the information together without having to search for them in separate folders or apps.
• Audio Recording: Yep. You can record audio while you create outlines. Imagine the benefit in class or in business situations. No need to fear that you miss something important anymore.

Overall, OmniOutliner can do quite a bit for you if you’re willing to invest some time to familiarize yourself with the app. Not everything is intuitive, but after spending some time with the templates and getting to know the keyboard shortcuts, the app will be of great help to you. The steep learning curve and the price are the only downsides I can see for this app. You can read an in-depth review of OmniOutliner here.

Price: $39.99 (Standard) or $69.99 (Pro)

Tree – Change Your Perspective

We are used to thinking of outlines as lists that start at the top of a screen or piece of paper and then run down vertically. It appeals to our sense of sequence. But what if you change your perspective slightly?

Instead of having sub-levels to a bullet point appear indented, imagine them popping up to the right of the main list item. So instead of reading an outline top to bottom, you’re reading it left to right. Confusing? See how it works here:

Tree offers you both your traditional list view, but also its name-giving tree view of an outline. It takes a little getting used to, but once you get the hang of it, it’s an awesome way to utilize any larger screen and actually see most of your outline at any given time without having to scroll.

Apart from this attractive feature, here are the aspects I liked most about Tree:

• Extremely Intuitive: There is basically no learning curve at all with Tree. Granted, for some stuff you have to look up a keyboard shortcut, but you can start using the app right away. Simply start typing, hit enter or tab and your outline creates itself almost on its own.
• Inline Notes: As with the above OmniOutliner, Tree also supports adding notes to an entry and they can also be hidden (to save space, for example, or to unclutter the view).
• Easy Text Formatting: Contrary to OmniOutliner, formatting text is a breeze. You simply select it and change it’s color, font or size as you would in Pages or any other text editing application.

I wish Tree would support styles as Pages does, though. That way I would only need to define the format of a level 3 heading once, for example, and it would be applied to all other heading of the same kind. But that’s a minor aspect to criticize.

Also, there is a “Label” function that allows you to assign a color label to everything, but all it does to change the color of the level indicator (the triangle or the bullet). It doesn’t change the color of the text that follows, which makes me doubt its usefulness. The color change is so small, it’s hardly noticeable. Also, attachments are not possible with tree. I tried to include a photo and it either links to where it’s saved locally or includes a link to a website, but not the actual file itself.

Apart from these three aspects, Tree is a wonderful application, which will appeal especially to those who can make use of the innovative tree view on large screens. Its ease of use and virtually non-existent learning curve are great for beginners and advanced users alike. You can read more about Tree in our in-depth review here.

Price: $14.99

Process – The Everything-In-One Application

Jumsoft is a well-known maker of Mac applications, among them Money and Relationship. For our article here I’m taking a look at their outliner app Process. I gave it a try a couple of years ago and wasn’t too impressed, but it has matured and become a real contender.

As with Tree, you can start using the application right away, the basic functions are intuitive and provide immediate results, even though not everything works as expected and I was forced to resort to mouse-clicks a couple of times instead of being able to use the app entirely via my keyboard.

To utilize all the power of Process, you’ll need to consult the help or at least read through the feature description on the app’s website. A template file or at least some sample data would go a long way to help a new user get started; maybe that’s something that Jumsoft will incorporate in the future.

The thing is, Process is quite powerful, but you don’t see it right away. Of course, it can do outlines, but there is so much more:

• Color Coding: To make long and complex outlines more readable and find important information quickly, you can color code entries by priority or simply assign them a label. Priority colors appear in a separate column, while labels color the entire row of an entry.
• Styles: Even though the styles don’t work automatically (set a style for a certain level of an entry and have it automatically use that style), it’s nice to have them at all. There are six presets which change the color and/or font of an entry, but you can’t change a style itself. You have to work with what’s included.
• Project Management: Process is quite adapt at managing projects; it allows you to assign a start and due date for each entry as well as an alarm. More than that, you can actually share your project with others on the same network. If you work within  a team, that might just speed up your workflow.

The most awesome thing about Process is the Sources Panel, though. It holds all your notes and source files. For example, if you want to add additional information to an entry instead of using inline notes as in Tree or OmniOutliner, you’d put them into the sources panel as a note.

You can add pretty much any file there, too. I’ve tried it with video files and even a Markdown file and it shows them flawlessly in the preview window. Even better, you can add URLs and the entire website is being previewed in the sources panel as well. It’s really an awesome way to keep all your documents in one place, so far only rivaled by OmniOutliner.

Overall, Process is a pretty neat application that can do a lot more that is obvious at first glance. In my eyes, it’s geared mostly towards project management needs, even though other types of outlines are possible as well (story boards, for example, will work fine in here too).

Price: $38.99

Circus Ponies Notebook – It can do outlines, too

Notebook by Circus Ponies is a very powerful application, which is aimed at replacing your analog paper notebook with something more powerful and digital. It can be used for virtually anything that you can do with pen and paper, but the option that interests us today is of course the outline function.

It utilizes the traditional way of outlining by creating a top to bottom list of your items. Through the usual keyboard strokes – enter and tab – you can create indents and thereby nested lists. It’s easy to start with, but if you want to harvest all the power of NoteBook, you’ll need to do some exploring, which won’t take long, but it will enable you to do the following:

• Checkboxes: Add checkboxes to your entries, either to all of them or to just some, to mark tasks as complete or parts of your lists as done.
• Assign Priorities and Due Dates: It’s not the most beautiful or elegant approach to task management, but if you need those information, NoteBook offers to include it.
• Add Address Book Information: If an entry can be linked to a person or organization, simply drag an address book entry to it and you get a small sticker to the left of the entry. By clicking it, all the contact information is revealed and you can even send emails from right within NoteBook.
• Highlights: Use different colored markers to highlight a word or an entire entry. It helps to structure your outline and make certain entries stand out more.
• Audio Recording: Just like in OmniOutliner, you can actually run an audio recording while working in NoteBook.

Now, that alone is already pretty nice for an app that doesn’t specialize in outlining. But what’s really great is the summary option of NoteBook which can pull all of the above information together and display them on separate pages.

It’s called the “Multidex” and it dynamically searches your notebook for highlights, attachments, to-do items or Due Dates. That comes in handy if you have these information scattered across several pages, like you’d have in a normal, paper notebook. Every meeting brings to-do items and due dates, but they are on separate pages. Instead of leaving through the entire notebook like you’d have to do with paper, NoteBook by Circus Ponies pulls those information together.

NoteBook is especially useful for those who don’t need or want an outliner-only app but are looking for an integrated approach. NoteBook can be used for class notes, meetings or pretty much anything else with the added benefit of the outliner function paired with the powerful Multidex.

Price: $59.99

TaskPaper – It’s Just About Your List

Do all the other apps look great, but all you want is something rather simple with preferably no learning curve and not too many options? Well, of course there’s an app for you as well.

Hogbaysoftware is known for its minimalistic apps, especially WriteRoom. But it also has a fantastic app called TaskPaper, which is a wonderful down-to-earth list app that can be used perfectly for outlining.

The benefit of TaskPaper is that it doesn’t require you to learn anything at all. It also won’t distract you with a ton of buttons or context menus. When you open it for the first time, you’ll see a short explanation of how the app works and how you can use it exclusively through the keyboard. There are about three or four keyboard strokes to remember and that’s quite manageable for pretty much everyone, I think.

TaskPaper is really just about lists, but you can structure them by using styles for entries. Headings can be styled as “Projects”, tasks are always leading with a dash and Notes can be added anywhere and they are slightly grey. Of course, color doesn’t really matter since you can apply different themes to TaskPaper (there are some included with the app and others can be downloaded from the website).

I’ve been using TaskPaper a lot in meetings and I found that its lack of options has been extremely helpful. It allowed me to type very fast, use less than five shortcuts to format entries as I typed them and have a ready-to-mail-around document by the time the meeting was done.

Of course, there are no capabilities of including attachments, setting due dates or formatting text, but if you only need an app that allows you to focus on what’s going on around you instead of worrying about how to write down what’s important, then TaskPaper definitely is worth your attention.

Price: $29.99

Verdict

As I said in the introduction, this article is by no means a complete list of outliners out there. But the ones I compared here have all their own strength and weaknesses, are all perfect for certain purposes and less optimal for others. I hope we were able to give you an introductory glance at what outliners can do for you in your educational, business or private environment.

Have you ever used an outliner before? What are your experiences? What is it that you look for most in such an app? Let us know in the comments.