Software Review: Leap 2 for the Mac, A Compelling Tagging Solution

The latest version of Ironic Software’s Leap helps tagging live up to its hype as a solution for making sense of your collection of digital data, whatever it might be: combine OpenMeta-based tagging with the Mac’s built-in Spotlight, and you may have all you need to keep track of it all.

What to Do With All That Data?

Like many people, my mountain of digital data — text documents, web pages, spreadsheets, photos, videos, etc. — is growing faster than the rate at which I want to keep dedicating brain power to keeping it organised or remembering where it all is. I already use utilities like LaunchBar and Default Folder X to help me navigate quickly to items regardless of where they might be on a hard drive, and I’ve spent quite a bit of time with ‘repositories’ like DEVONthink Pro Office, which can both collect and discover relationships between arbitrary sets of documents. But while reviewing DEVONthink, it struck me that often all I really wanted was a good way to store and retrieve things, and in those cases I wasn’t really taking advantage of that application’s sophisticated AI core.

Enter tagging, which promises to free users from the confines of proprietary repository or database systems, keeping their data right there and visible in the good ol’ Finder, while simultaneously offering freedom from the confines of folder-based filing systems.


Leap, by Ironic Software, is a major player in the tagging world, and Ironic is a driving force behind the emerging OpenMeta standard for tagging. I jumped at the chance to take a look.

If you’re already au fait with the tagging scene, you should skip the next section and go straight to ‘Using Leap’ below; otherwise, what follows is a quick introduction to what tagging is and how it can be used.

A Quick Aside: What Does Tagging Let Me Do?

Imagine being able to find files on your computer based upon what they’re about — not just based on what they contain, but rather on what you have decided they’re about. For example, it wouldn’t be unusual to want to find all your receipts (regardless of whether they contain the word ‘receipt’ inside them or have the word ‘receipt’ in their name). Maybe you have all your receipts stored in a particular directory, so you can already do that anyway. But what if you wanted all your receipts that were for business expenses incurred while visiting foreign countries during the years 2002-2006? What about all the receipts which were either business or personal and not in foreign countries? Could you do it with your existing hierarchy of folders? It’s a bit of a contrived example, but tagging can make it easy to retrieve this type of information. More accurately, tagging can make it easy to store data in such a way that retrieving it in this way or many other ways later on is also easy. Unlike the traditional hierarchy of folders, where any given file exists in exactly one folder hierarchy, any given file can exist in multiple sets of files which share a given tag. So a file tagged with ‘business’, ‘receipt’, and ‘foreign’ appears in three overlapping sets, one for each of those three tags — and can be retrieved with a search on any or all of those tags. Tagging opens up myriad new ways of getting at your data, regardless of where your files live in the folder hierarchy.

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Many people will be familiar with the idea of tagging from applications like iPhoto, where you might, for example, tag all your photos of birthdays with ‘birthday’ and all your photos of parties with ‘party’. Later on, you could see all photos from birthday parties with a search for photos with both tags. For the last few years, applications have been springing up offering various ways of applying tags to arbitrary types of files, not just photos, and Spotlight has supported searching for certain types of tags (more on that later) for awhile now, using the syntax ‘tag:mytag’, where ‘mytag’ is the tag in question.

Leap is a front-end both for tagging and, more significantly (since there are plenty of interfaces for tagging) for retrieving tagged files, using an emerging tagging standard called OpenMeta, which was pioneered by Ironic Software. OpenMeta is now supported by a wide range of different applications, meaning that Leap’s way of working with tags will inter-operate smoothly with many different tools.

Using Leap

The developers themselves can describe far more efficiently than I can just how you might want to use Leap, and I’ve included links for a few of their screencasts here. If you’d like to get a feel for what is possible, and a look at the visual aspects of the interface, I’d recommend taking a peek.

Leap tour

Tour of Leap

Leap versus Finder

Leap vs. Finder

Leap versus Spotlight

Leap vs. Spotlight

In a nutshell, Leap provides a view of your hard drive’s contents which can be constrained by any combination of file type, location, tag, date, and user-assigned rating. You can view by sets of tags (such as ‘receipt’, ‘business’, and ‘foreign’), and you can easily toggle tags on and off to change the set of tags being searched. Mousing over results immediately shows where they live in your folder hierarchy, and mousing over with the option key held down shows the document magnified with a ‘loupe’; selecting and hitting space provides a standard QuickLook at the document. Because Leap is tapping directly into Spotlight, it is relatively speedy — significantly faster under Snow Leopard than Leopard, in my experience — with the drawing of preview images often taking longer than finding results in the first place.

Leap’s view of your files is highly configurable, although I have to say that even after reading the manual, it took me some time to wrap my head around the basic paradigm sufficiently well that I would turn to Leap to help with any real work, as opposed to simply testing it out and marvelling at how amazing it was to see the contents of my hard drive in such a novel way. It’s undeniably powerful: as far as I’m aware, nothing else can give such a visually beautiful and eminently usable look at my files. And the basic paradigm isn’t really that hard: tell it where you want to look and how you want the results to be filtered, and apart from a few subtleties, that’s pretty much it. But if you’re accustomed to thinking more about the where than the what — or if you’re accustomed to jumping straight to documents via something like LaunchBar — then it may take some getting used to before it begins to save time, rather than simply being a remarkably cool novelty.

As for the other end of the tagging approach to organisation — i.e., the actual tagging — Leap is more than capable: select a file, hit a keyboard shortcut, and up pops a HUD, complete with tag auto-completion and a clickable list of recently used tags. I have absolutely no complaints about the built-in tagging HUD, but in actual fact I hardly ever use it. The reason I rarely use it boils down to how I’ve used Leap itself, which is primarily as a tool for finding and visualising. In other words, I tend to use Leap when I’m looking at or for something, not when I’m actually creating something or storing something. In the latter cases, I’m more likely to use the OpenMeta support built into Default Folder X or, for tagging directly from the Finder, the excellent and free little application called Tagger, by Ali Rantakari. (Ironic Software provides their own free tagging application called Tagit which — ironically enough, heh heh — used to be called Tagger, but in my opinion Ali Rantakari’s Tagger is much better.) By assigning a system-wide hotkey to Tagger, I’m able to select one or more files in the Finder, hit the hotkey, and quickly tag the file(s) with a minimum of fuss. (I had previously done something similar using Keyboard Maestro, AppleScript and Tagit, but Tagger makes it all quite a bit easier.)

For me, the end result of using Leap together with Tagger, plus Spotlight for basic and quick tag-based searches, plus the extra support from Default Folder X, makes a nearly perfect setup for adding a new tag-based dimension to my existing folder organisation. Tagging has proven so useful that for a subset of my files, I’ve actually just started dumping them all into one folder, relying entirely on tags to find them again. Curiously, for me, Leap is actually the least-used part of the whole ecosystem that makes tag-based organisation attractive — I use Tagger at least ten times as often, if not more — yet it is also the part that has nudged me off the fence and into the ‘early adopter’ camp for tag-based file organisation. Even if I don’t use it all that often, just knowing that I can use it when I really need it makes the difference for me between using and not using tags.

But there is one final fly in that ointment…

A Very Important Caveat

There are at least a couple of significant caveats — and one very important one — that you should know about if you’re considering taking the plunge into tagging as a way of augmenting or even replacing your existing filing methods.

One is that the specific methods being used by OpenMeta are not explicitly supported by Apple, and the would-be standard relies on some trickery to coax Spotlight into indexing the tag information. Concerns have been expressed by many people that if Apple should decide to change how certain things work, OpenMeta tag data could wind up inaccessible.

Another caveat is that poorly behaved Adobe applications are known to mess with the storage of tag information during the saving process, and while the developers behind OpenMeta have come up with a work-around, it is exactly that — a work-around — and not really a robust solution.

Finally, and most importantly, it has recently (as of this writing in October 2009) emerged that changes made in Snow Leopard could potentially result in a document’s tags being lost when the document in question is modified and saved again. The problem appears to derive from the fact that Leopard ensured that a file’s extended attributes (used by OpenMeta to store tags) were preserved when an application saved the file, whereas Snow Leopard relies on the application to preserve the extended attributes — and many applications do not do so.

As of this writing, there is some controversy over the proposed solution, and while there is clearly a consensus that the problem must be overcome (or fixed by Apple!), it should still figure in your evaluation if you’re considering a move to tagging in a big way: nobody wants to spend time tagging files, only to discover somewhere down the line that the time was wasted.

Having said all that, my own view is that the benefits of tag-based systems outweigh the difficult-to-quantify risk, and I am willing to give it a whirl. Your mileage may vary.

Can it Replace Databases and Other Heavy-Duty Repositories?

Does Leap (plus Tagger!) provide a sound alternative to heavy-duty packages like DEVONthink for those situations where you might just want to store and organise and retrieve but not necessarily perform any artificially intelligent heavy lifting based on how different pieces of text relate to one another? For my own usage patterns, the answer is an unqualified yes.

System Requirements and Pricing

Leap requires Mac OS X 10.5.5 or later and sells for $59; it is also available as part of a bundle for $69, which includes all of Ironic Software’s other commercial products (namely, Fresh, Deep, and Yep).

Please see the Ironic Software site for full details.

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