Depressingly Accurate Thread

I’m an owner of Pro versions of the latest OmniOutliner on macOS and iOS, so I’m not a hater, but there is a worryingly accurate thread over on the MacPower users forum about under-utilised software.

I have participated in the thread, but the overwhelming winner is OmniOutliner.

The view is that it’s too fiddly, too slow, and too document-centric (as opposed to a document library model) to be of much use.

I really hope the Omni team take a look at OmniOutliner for the future, because I think it really needs an overhaul to be able to last into the future.

I don’t find the current version to be “fiddly” or “slow” at all. I run much of my life & projects using it. I find the outline metaphor by far the best way of managing information that doesn’t lend itself to a simple, uniform structure, and OmniOutliner implements that metaphor in more usable way than anything else I’ve found.

I don’t find the document model to be an issue; in fact, it’s an advantage from a security perspective. I can store safely outlines with confidential client information on an encrypted disk partition. I wouldn’t dare store this information in OneNote or another online product, despite their lightweight security features.

The one thing I miss in OmniOutliner is integration of simple OmniFocus-like features: the ability to tag and prioritize action items and then view and manipulate them in a separate action-oriented view that’s still tied to the underlying outline. Having to maintain duplicate information in a separate application (OmniFocus) for this is just too cumbersome. Various outline-based products have had this capability over time–the most recent being Circus Ponies Notebook–but alas none of them have survived.

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Your post caught my eye, because I, too have some concerns, but not entirely related to the ones you raise. (I think the document model is a good one for the same reasons @fssbob indicated). I’m a trial lawyer. I learned outlining in fourth grade and I think of just about everything in life in terms of outlines. I have OO 5 (Pro) on my MacBook Pro and OO 3 (Pro) on my iPhone X and iPad Pro. I am very impressed with the tool and I really like it a lot. It works exceedingly well, and once you invest some time setting up templates (if you are picky like me), it’s really quick and easy to use. I have not had any issues with it being fiddly.

I used to create every single document that I made in MS Word, but there are a lot of things that a word processor is not well suited for. One of them is outline. I have begun using a series of OO outlines as my primary knowledgebases for trial practice topics, procedural law, evidence, law, and all the substantive legal topics that I deal with. (I also have migrated all my personal knowledgebases into OO outlines: music; communication skills; my computer file organization system; and the list goes on.) It is easier for me by a factor of about 100 to capture all the information that I would learn about into a place where I can easily find it again later.

I also use OO for making trial outlines. In a trial outline, I gather all the facts, legal issues, witnesses, arguments, defenses, and rebuttals in a way that never worked very well in MS Word. This is where I see the problem with OO. As a partner in a law firm, I collaborate with a lot of other people on my team and we all need to use and contribute to the trial outline as the case develops. But we are not a Mac shop, so I tend to keep the outline for myself and just share PDF exports of it periodically. That is not an ideal situation to be working in.

My office is not going to be adopting Macs across the board, and I’m not sure the Omni Group should be spending time porting this tool to Windows. But I wish there were some way I could collaborate in my OO file (without having to export and re-import). As it stands, I think I may have to go back to MS Word to solve this problem, which I don’t want to do. OO is just about perfect for building these trial outlines.

All this to say, I think OmniOutliner is a fantastic tool. But I’d really like to be able to use it more widely especially in environments when many people will have to be contributing to the document.


The combination of a scriptable outline with field columns is unique, and when that’s what I need, I do reach for OO.

In practice though, most of my outlining is done in Taskpaper (also a scriptable outliner), mainly, I think, because it feels faster and more flexible.

I do wonder whether the flourishing of plain text apps, not least on iOS, and the widespread adoption of Markdown, hasn’t made users a little more impatient (consciously or otherwise) with modal widgets.

OO is excellent and approachable, and has a very fast and interesting new scripting API, but there is an inescapable element of friction in continually having to enter and exit little ‘fields’, or frequently having to position the cursor and check the current selection type before typing …

Perhaps 10 years ago we didn’t notice that so much ?

A bullet that’s just another character is somehow simpler and faster to deal with …

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It’s accurate that OO can be that unused app, but I don’t find it depressing. Like someone said, if they have tabular data, there’s Excel. If they’re just writing an outline, there’s nearly any decent text editor. OO is great when you need both those things together, and for whatever reason people think they need that combo and learn they dont after purchase. That’s fine, other than maybe being a sign that people aren’t good at thinking of good metadata for their outlines.

I agree that a portable format would help those who need to interop with Windows/Office users, but the common issue is aspirations not leading to effort. :)

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I don’t think that thread is necessarily very representative. It can be difficult to get an idea of how the public actually thinks about a product because of the phenomenon of “me too”, when people see something they agree with in a forum they chip in with their experience backing that up. Maybe they have other apps which they don’t use either and if someone had mentioned one of them then they might have done a “me too” for that one.

While complacency is very bad I think the Omnigroup should be careful not to try to turn OO into something it is not. Although I am very new at the forum I had actually used OO for many many years. I remember when it was the new kid on the block.

I think expectations have changed since the time when OO was created. The idea of plain text and library style storage is now very much in vogue but when OO was created people were still trying to get away from that ☺

Personally I use OO a lot. I think Omnigroup have done an excellent job of bringing OO into the IOS world. I love the IOS version which I got recently because I bought an iPad for the first time. The sync with Omnipresence and Omni Sync Server seems to be very good.

Obviously OO is not going to be like, say Ulysses or other text only apps using markdown, but it is a very different animal but one which has its own abilities which they do not have.

Personally, I like being able to bold and underline words. I remember when I first used a Mac back in the 80s and It was just wonderful to be able to do things like that and I don’t want to go back ☺


“OmniOutliner. While I’m using it (rarely) I think ‘why am I doing this – I already own Excel’.”

I have no idea how these people are using Excel.