New outliner for the Mac is slick but needs work

[Important note: Because this initial “review” of Outlinely was so riddled with errors, I decided to write a whole new review, which you can find here. I’ve decided, at least for now, to leave this review here, since some other websites point to it.]

Warning: Do not buy this app! See the update at the bottom of the review!

(See new update at the end.)

(I’ve also updated a few inaccuracies I had with my original post. Thanks to the Taking Note blog for pointing out my errors.)

Thanks to the eagle-eye of one of the folks over at, I was made aware today of a new outlining application for Mac known as Outlinely (requires OS 10.8 or higher). I’m not so crazy about the name, but for the most part, I like this app a lot. The introductory price of $5 makes it a real bargain. If this application were for Windows, it would instantly be one of the top outliners on that platform — which, admittedly, is more of a commentary of outliners for Windows than accolades for Outlinely. Nevertheless, Outlinely is equal parts slick and simple, and looks like a nice option for cranking out notes and gathering thoughts.

Outlinely is a new option for people (like me) who use outlines for writing, planning, thinking, tracking, note-taking and more.

Outlinely is a new option for people who use outlines for writing, planning, thinking, tracking, note-taking and more. (The note-style text is easier to read than it appears in this screenshot.)

Here are some of the features I like:

  • Clean interface that does feel a lot like a word processing editor, which is one of the goals stated by the developer.
  • Versatile export file formats. I haven’t tried them all, but the ones I did worked well. See below for a screenshot of the markdown export I opened in Ulysses III. Here are the options:
    • OPML
    • PDF
    • HTML
    • RTF
    • DOC
    • Markdown (it adds the markdown code for you)
    • Plain text
  • Can focus in on one topic at a time (see screenshot below).
    • You can focus on a topic by pressing command-return.
    • Unfortunately, there does not appear to be a keyboard command to unfocus. You’ve got to mouse over to the little magnifying glass in the bottom left corner and click.
    • It is a little strange that the developer suddenly relies on mousing, when other common mouse-type actions (like drag and drop) are absent. (Note, there is a command to unfocus while in focus mode, but it appears under the EDIT menu, which is a strange place for it. Or you can tap the ESC key.)
  • Toggle a topic as “done” or “undone” using command-D keystrokes. Done topics are grayed-out and crossed out.
  • Topics can have notes.
    • Notes are not included with the export.
    • There is one major issue with notes… see below.
With Outlinely you can focus in on one topic. You can also change the font, the font size, and the color theme.

With Outlinely you can focus in on one topic. You can also change the font, the font size, and the color theme.


Outlinely has a number of quirks and omissions. Some of these may be intentional to keep the app simple. Some may be errors. And some may be simply that the developers haven’t gotten around to them yet. Here are the ones I’ve uncovered, in no particular order:

  • No drag and drop for re-organizing topics.
    • This isn’t so bad, but some people might miss it.
  • Supposedly you can add hot links, but I can not figure out how to do so, and since the help file is not up and running yet, I can’t learn the answer without turning to the developers. (Note, there is a help file in the form of a native Outlinely file. It didn’t originally open for me due to the same problem I was having regarding the corrupt extension database.)
  • Can’t select or change the bullet/labels for the outline. In fact, bullets only appear for topics with sub-topics. Otherwise the indication that the text is part of a separate topic needs to be inferred from the slightly larger space above it. I’ve found that when topics run on for several lines, and you have a few of these together, it isn’t instantly clear where one topic ends and the other begins. I do like the fact that the editor window isn’t cluttered with bullets, however.
  • Can only change the font for the entire outline, not word for word or topic to topic. You can, however, bold, italicize, or underline selectively.
  • When you hit RETURN at the end of a topic, a new sibling topic is created. This is expected behavior, but if you have already created a note for a topic, then, hitting RETURN creates the new sibling topic between the first topic and its note. This seems like a bug. The new topic should be created beneath the first topic AND its note.
    • In fact, I’m not sure how you create a new topic after a topic that has a note attached. The only way I’ve found to create new topics after a topic with a note is to create them after some other topic without a note, then move them to their rightful place.
  • I am not crazy about the fact that the bracket symbol keys (in conjunction with the option and/or command keys) are required for moving topics around the outline.

Beyond this list, there are clearly some pieces that are not finished yet. The “show toolbar” and “customize toolbar” selections under the VIEW menu remain grayed-out and inactive. Clicking “Outlinely Help” under the HELP menu achieves nothing.

This is the Outlinely document shown in the above screen shots, exported as markdwon then opened in Ulysses III.

This is the Outlinely document shown in the above screen shots, exported as markdwon then opened in Ulysses III.

Clearly, the developers have a bit more work to do. Outlinely does not and (I hope) never will compete with a full-featured outliner such as OmniOutline. It lets you build structured documents quickly and easily, and gives you the tools to export your work to a bunch of other formats. I like it now as is. Once the developers add a few missing features and fix the “notes” issue, it will be a terrific little app.

Update: This app is seriously flawed. As I was running my little test on it, I never bothered to try to close the file and re-open it. I mean, why would you worry about that? Well, with this app you need to, as it won’t even re-open files that are supposedly in its own file format.

When you save a file, you have two choices: Outlinely Document and OPML. Well, saving the file in either format results in a warning when you try to re-open it that the program can’t.

Outlinely failing to open its own file!

Outlinely failing to open its own file!

Just for the record, I never opened or saved the file using OmniOutliner. I experimented with other files and got the same result, so it isn’t just one corrupt file. How could someone sell an app with this problem, and how can Apple sell it through the App Store? I’ll be contacting the developer and will post a resolution here, if and when it comes.

Update 2: I wrote to the developer and received a response within an hour and a suggestion for how to fix it. Turns out the problem resided in a corrupted associations database on my MacBook. The developer gave me a fix and now Outlinely indeed opens its own files. In six years of computing with Macs, I’ve never encountered this problem before.



  1. Why do you think development of outliners has become such a dead end recently? Are the technical demands to making it work in a browser environment the problem?

    1. That’s a great question, and I wish I knew the answer. There are at least a few decent browser-based outliners… Workflowy comes to mind. There are more good outlining options for Mac than for Windows, so maybe developing for Windows has something to do with it. Thanks for reading my blog.

      1. Your blog and your contributions generally have been insightful, and you’ve even made me regret not having any conceivable use for Tinderbox. Thanks for your response. I think it has to do with the tension between outline main topics having to be connected to each other; if they could float like clouds you might come up with a different paradigm. Something like what Scapple brings to the table.

    1. Carol, it is not too early in the morning (well, maybe it is, but that’s not the reason you’re having trouble). As I was trying to come up with a solution for you, I discovered a major problem with Outlinely. It does not even re-open its own files, let alone provide a way to import from other apps. I’ve updated my post with this distressing news!

    2. Hi, Carol, As you may see from the updated update to my post, the issue with opening files with Outlinely has been resolved. The error was with my machine. On to your question, I was able to export an Opal outline to OPML, which opened just fine in Outlinely (after correcting the issues with my computer). Did you give that a try?

  2. What advantages does this program have over Opal, which has been out for years, is rock solid, fast, and supports drag-and-drop for moving outline items?

    1. I have been an admirer of Opal, but sadly it has not be updated in five years. But I will also say that Outlinely in fact has at least a few advantages over Opal at this stage. For one, you can create notes that are part of any topic and move with them as you adjust the structure of the outline. Second, Outlinely is more keyboard friendly. For example, to indent a topic in Opal with the keyboard, you need to press three keys: shift, command and “R”. It just takes the TAB key in Outlinely. To Opal’s credit, however, I like how the keys required for moving topics make sense (in addition to shift+command they are R for moving right, L for moving left, U for moving up, and D for moving down). Also in fairness, it takes three keystrokes to move a topic up or down in Outlinely. So it is a close call, certainly. If you already have Opal and are happy with it, there is no reason to change. But for those looking for an outliner, Opal is also more expensive than Outlinely, and there is no evidence that it will be updated again (but I don’t know that for sure).

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