Possible Future for OmniOutliner

Does anyone wish OmniOutliner was a database like OmniFocus? I do.

  • Open one app
  • See every outline on the left like Projects in OmniFocus
  • Modify outlines with left and right inspectors
  • Quick open for opening various outlines
    • Quick adding text to outlines for organizing later. (At least you can capture the thought for that outline. Maybe timestamped rows like OmniFocus actions for reference. Let’s forget about this rabbit hole for now.)
  • Renaming Outlines like Projects in OmniFocus versus dealing with individual files and filenames
  • Regular database backups like OmniFocus
  • Syncs like OmniFocus
  • This may help with linking across multiple documents since they will be in one place
  • Who knows what is possible with Omni Automation

Managing files is not fun. It requires disciplined habits or it will become a mess. I think having a database like OmniFocus or Bear is easier to work with for many occasions. If I manage files, I prefer them to be plain text because they will open anywhere. When it comes to advanced proprietary awesome apps, like the ones from The Omni Group, I don’t want to manage the files. I can’t edit them anyway without the app itself, so the app might as well manage the data for me. OmniFocus does a great job with this, and I’m spoiled by it.

Any thoughts on this as a possible future for OmniOutliner?


I would LOVE this. I hope it’s considered by Omni.


Agreed! I have got into trouble locating files between my devices, depending on where they were saved. I also get a lot of conflicting versions of the same file which is a real nuisance.

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I prefer individual outlines, because of the flexibility it offers to group outlines with other related documents.

You can solve these problems with the current version of OO, using some helper apps.

I have a Hazel function that files any OO document found on the Desktop into Documents>OmniOutliner. It’s very rare for something to get lost.

I also have a saved search in Houdah Spot that finds every OO document on every hard drive. It brings them up quickly, and you can refine from there to search for a particular outline.

If you really want a database with tagging, etc. I recommend Devonthink Pro Office. You can set up a watched folder, and every time you save an OO document to that folder, it will be auto-imported into Devon. Then you can search, tag and annotate as much as you want.

Have you tried Resilio Sync? It puts a folder on all your devices, and it stays synchronized. It’s a great, rock-solid app. Syncs quickly, too.

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No I haven’t heard of it but will look into it thanks.

I use DEVONthink but if you save an outline there the iOS version can’t open it. But agree the Mac version is a good alternative.

The macOS version of DEVONthink cannot open OmniOutliner documents either, but it can display them as OmniOutliner for macOS has a Quick Look viewer. It would appear OmniOutliner for iOS does not (yet) include Quick Look, thus the reason that the contents cannot be viewed (in DEVONthink or other apps e.g. Files.app).

At this point, the best way to open OO documents in a DEVONthink to Go database is to use the Files.app to browse the DEVONthink database and click on them there, where the document will immediately open in OO.

It would be nice if the Omni and DEVON folks would get together and discuss how add this functionality to DEVONthink to Go, where clicking on the file in a DEVONthink to Go database opens the document in OO, same as how it works with Files.app.

I would also like this, or some version of this.

Another possibility might be to allow for multiple outlines in one document - similar to multiple canvases in an Omni Graffle document.

That would allow me to group related outlines together in one document, which is mostly what I am looking for.

(Although I have also run into issues with syncing OmniOutliner documents across devices, and get conflicts more often than I would expect. I don’t think my suggestion would address that issue.)

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I appreciate the responses because I am curious how other people feel about this database approach.

Wouldn’t a link to an OO database outline be a solution for grouping related documents? If you have an OO file grouped with other files, you still need OmniOutliner to open it. Opening this file can launch OO showing the one document or it can launch the OO database with everything, like OmniFocus. And your link could focus on that outline if you don’t want to see anything else.

I am using the apps you listed. I have Hazel, DTPO, and Workflow organizing all of my individual plain text files, and they are named and filed to my liking between iOS and macOS. They are amazing apps! But this gets back to one of my points that I believe managing individual files requires disciplined habits. After creating these habits over the years then using a smooth database like OmniFocus, I find it a joy to use when dealing with proprietary software. Some examples are:

  • Its background file management, so you don’t have to worry about saving and naming before you get going or leave the app
  • Keyboard shortcuts for bouncing around the database for quick management
  • Export options for sharing and archiving
  • Automation for even more exports and data manipulation (coming soon)
    • Even though OO has this feature, I wonder what it’ll be like working within a database with every outline in one location

If I could open OmniOutliner documents (without exporting) with different apps, like I can with plain text files, then I would see the benefit of grouping those files with related documents. I see how OmniFocus handles large amounts of data, and I dream about OmniOutliner doing the same thing. Right now, I always open the same handful of outlines for my daily workflow and and then merge all windows as tabs before I get going. It already feels like a database at this point. Then I crave a quick entry feature being thrown in an outline before the thought is lost. I could quick entry some text to an Inbox level in one of my outlines.

When I create one-off outlines, they always wind up somewhere on one of my many sync services and I may want to refer to them later, so I think about having a dropped feature like in OmniFocus for archiving and maybe referring to it later. There are times I’ve deleted outlines, and I wish I didn’t. I would love to drop or archive them and bring them back later if needed. And yes, I can create this workflow with folders and disciplined habits. I’m just spoiled by that awesome OmniFocus database. :)

All the eggs in one basket would be a negative for me. In fact, even though I’m addicted to OmniFocus, I’ve started using TaskPaper for writing to-do’s. I use DEVONThink, so if I have things to put in a to-do list for a particular writing project, it goes in the right folder in DT along with the outline and other files.

While I don’t directly manipulate OO files, I make good use of OPML exports. I have a Python script that will flatten an OPML file for import into Scrivener, giving me the one or two levels I want to see in the binder. All the subtopics go into the synopsis for each Scriv document.

If you want everything in one database, you don’t need any change to OO. Turn on the sidebar, collapse all the entries, and treat each top level topic as a separate outline. While you’re focused on it, you won’t see any of your other outlines.

I like being able to archive a project with all it’s stuff in one place, usually in DEVONThink. Sometimes I’ll come back to something a year later, and I’d like to keep all my work in one bundle. I usually have a word processing file or a Scrivener project, a mind map that’s sort of an inventory of ideas, my OO outline, perhaps a TaskPaper to-do list for that writing project, and various notes and web references.

Since an OO outline generally goes with one body of work, I would regret breaking the outline away from the work it supported.

I agree with the premise of a database. Basically, I am imagining not so much OmniFocus, but Bear, with each note being an outline, rather than a text file.

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Given that I’ve literally spent (wasted?) multiple hours this last few days being CRIMPy and angsty about my note taking workflow, I agree with this. I’m currently playing with Outlinely and Dynalist, both of which are basically outliners plus some TaskPaper in a database (Outlinely is based on Workflowy, of course).

All of them have issues, none of them work perfectly and I’m about ready to go back to yellow post-its and a pen. :-)

Ok, maybe not. But I need to stop wasting so much on deciding which note taking app to use and just TAKE NOTES.

I like all of the eggs in the OmniFocus basket due to quick entry and autosave in the background during opening or closing the app while syncing the data. I never get conflicts. Since OO is a great tool, I’m trying to use it as a quick entry tool, but it’s hard if you don’t have an outline already open, saved, and setup properly. I feel as if managing individual files creates these roadblocks versus launching a database and jumping right into your data.

I’ve tried this, and I still struggle with it if columns and styles are introduced. You would be forced to create the same look for each section of data with styling and columns.

This is why I open up multiple OO files and set them up as tabs because they have different level styles and a different amount of columns. It would be great to have multiple outlines on the left within a folder, like OmniFocus, and click through each one. Possibly even Quick Open for the next outline that isn’t within that folder. It would be faster to see all of them on the side (or focus to hide others) without having to organize them via tabs before getting started. I think more data would be tracked in OmniOutliner with this approach because you’re a couple shortcuts away from launching another outline, or another set of data.

You could drag outlines to different folders, link them (or rows), drop them, delete them, duplicate them, etc. I’m sure most probably can picture the speed of this approach since most of us use OmniFocus to some degree and have manipulated data within its database. The more I think about this, the more I want it. No more creating and saving new files. Just Command+N and start outlining. And you can format later with styles and columns if needed.

Also, I know this is easier said than done. I don’t expect Omni to make this overnight or at all. :) This is just my opinion, but I feel OmniFocus is their flagship app since it’s so smooth and polished with a database and separate syncing compared to individual documents. So many things are handled in the background making our lives easier. Maybe Omni created OmniFocus by learning from their other apps, now I’m picturing OmniOutliner learning from OmniFocus. It’s sort of the same app.

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Enthusiastic +1

This really is something that often steers me away from OO. Just too much overhead for light outlining needs

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What I want OO to support is multiple views for the same outline similar to the vim text editor so I can edit one section while viewing another and vice versa.

Yes, or Ulysses as another example. I end up doing a lot more outlining in those programs than I otherwise would if OO had an easier way to view and manage all outlines.

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Big yes for me! Along the lines of Ulysses, or even to a lesser extent what IA writer has implemented with a built in explorer bar that you can link folders too etc.

This would not work for me, unless it was completely optional and would leave the existing one-file-per-outline workflow mostly unchanged (visually and conceptually uncluttered).

Organizing data by file type instead of by project context doesn’t make any sense to me. That would leave me with a database of outlines, a database of PDFs, a database of web archives, a database of images etc, with no good way to group related information together.

I want to have personal and work related documents separate, and I want to be able to share them individually and not in bulk.

OmniFocus is a special case, given that it ties active projects together. But then it only contains scheduling information and not the project data itself, except for a small note, and/or a link. And even there I almost always use the “Focus” feature to narrow down the things to my current work area.

I’m intrigued by the newish Agenda note taking app, but the fact that it stores all documents in a single database has stopped me from looking into it in details. The fact that you can’t even use Spotlight to locate notes inside the database turns it into a silo from my point of view.

Having said all that, storing multiple outlines inside a single container would sometimes be useful (similar to how you can store multiple sheets in an Excel spreadsheet). Normally this can be done via additional top level sections, but sometimes I would like to use different columns in different parts of the outline…

So after playing around with Outlinely and DynaList, I decided to say “no” to additional complexity and more apps and try doing a “monthly log” in OO. It’s a hybrid approach to what was suggested above. I have 1 file per month, but each month’s file is a collection of daily notes with Week of… being the top level topics and each day beneath those, and so on and so forth.

So far it’s working well, but I can see some limitations (particularly around the use of columns, which is perhaps not as a big a deal as it seems because the whole point of these light monthly logs is to be simple–columns are often unnecessary).

I’ll keep you posted with how it goes!

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