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Smarter Ways to Work with PDFs

by Giles Turnbull

One of the nicest things about Mac OS X is the effortless way it creates PDF documents in just about any circumstance you can think of. If you can preview something for printing, you can make a PDF of it with one additional click. It's one of the features that newcomers from the world of Windows always comment on, "Wow, you can make a PDF as easy as that?! Amazing!"

But there's a less attractive consequence of this remarkable feature: a build-up, over time, of PDFs all over your user directory. On my computer they're mainly invoices, e-books, receipts, travel documents, and anything "official" that I feel the need to save for posterity. Other people, especially those in academia, build up considerably larger collections of considerably more important material.

Spotlight does a great job of searching PDF content on your hard disk, but the default Spotlight interface is not well suited to managing a large collection of PDF documents. So, how do you manage it all?

That's what we intend to look at in this article. We shall be looking at how you can use the simplest of tools (including iPhoto and iTunes), as well as third-party applications built to offer document management features. We will also take a look at alternative PDF readers, in the event that Apple's own Preview doesn't live up to your expectations.

Start Simple

Let's start with the basic stuff, the software that comes with your Mac (or with iLife, if you have to purchase it separately). Both iTunes and iPhoto can import PDFs, but have different ways of dealing with them and offer quite different management options.

iTunes will cheerfully copy into its database any PDFs that you throw at it. Just drag them into the library, or onto a blank space in the sidebar to create a new playlist. By choosing the Kind criterion in the Smart Playlist dialog (Kind contains .pdf, or Kind is PDF document, you can create a new playlist that will display all your PDFs together.

Because iTunes is geared up for file metadata from the start, it provides a decent environment for managing small-to-medium collections of PDF files. It's unsuited to larger ones because of the large amount of time you'll need to spend entering more data to make it worthwhile. Every PDF you import will need to have meta information like Author, Keywords, and Comments.

Kirk McElhearn suggested that iTunes would be a good tool for musicians wanting to store their own digital copies of sheet music. He's right, but there are limits to what you can achieve.

It's possible to adopt certain metadata fields for your own purposes, say by using the Genre field to create a list of types of file. This is fine for basic-level use, but in the long term might be counter-productive. Professionals, and anyone likely to build up a very large collection of PDFs, need something that's built for the job.

That thing is not iPhoto.

You can add any document to iPhoto via the Send PDF to iPhoto control in the Save dialog, including PDFs. But what actually happens behind the scenes is your document is first converted to PDF (if it isn't one already), then converted again into a jpg image file, and that's what iPhoto imports. The end result is documents-as-pictures, unsearchable and not really much use for anything text-based.

What's strange is that Apple thought to include this Send PDF to iPhoto control in every Save dialog, but oddly didn't include a Send to iTunes option, which, given its better features, would have been a lot more useful. Of the two options, iTunes is by far the better.

Apps to Organize PDFs

What's needed for serious document management is an app designed for the job. Thankfully, there are several for you to choose from.

In this brief overview we're going to concentrate on apps that were built for management of PDFs. I stress the word management because there's a very large number of applications that will open, display, or edit PDFs, but those features are not the ones concerning us this time. We want to know how to keep PDF collections under control. We're also going to leave out apps that offer some degree of PDF organization alongside other information management (products like Yojimbo, DEVONthink, and EagleFiler), not because they're not great apps (quite the contrary), but simply because they've been discussed in great detail elsewhere.

So the apps we will concentrate on are organizers Yep, Papers, and freeware alternative PDF reader Skim.

Yep: iTunes for PDFs

Yep: iTunes for PDFs (Click to enlarge)

The first great thing that Yep does is run a complete scan of your hard disk, hunting down all the PDF files you might have lying around. It doesn't matter where they are or how you have them organized, Yep will find them and, when it's done, show you a window that's a hybrid of iPhoto and iTunes. Your PDFs are in the middle, ready for browsing.

Yep really does live up to its tagline, "iTunes for PDFs." It doesn't care where your PDF files are, but it will nonetheless make organizing them simple. The primary means of sorting in Yep is via tags, so your very first task when using it will be to go through everything it has found and add new meaningful tags on top of the ones that Yep automatically adds, which, to begin with, are based on the folder and file names it has encountered along the way.

What Yep won't find is PDFs stashed away in databases. If you already have a bunch of them stored in an app like Yojimbo, you'll need to export them into a folder somewhere first. By default, the app stores new files in (user)/Documents/Yep Documents, but you can tell it to put them anywhere.

The way Yep employs tags is its greatest strength. Everything you need to do in Yep can be done by browsing the tag cloud in the sidebar. The process of adding, searching, and managing tags is nicely made.

There's only one downside to this, which is that you will need to spend time tagging up your documents after moving them into Yep. This could be time-consuming for large collections, but would probably be worth doing nonetheless.

Yep includes a decent PDF viewer, but it lacks any features for making notes or annotations. It also has a Loupe tool for use in the main browser view, which makes it much easier to pick out something specific from a display of broadly similar text documents. It also reaches out to the academic community with a direct search link to Google Scholar. Overall, Yep is a very attractive and easy-to-use tool with some sensible and well thought out features. Development is very active and new releases are frequent. At $34, it represents excellent value for your money.

Papers: PDF Management for Academics

Papers: an academic approach (Click to enlarge.)

While you could argue that Yep and Papers are similar products, in the sense that they both manage collections of documents, in use they are very different.

While Yep has some features that may appeal to academics, Papers is designed from the bottom up for academic research. Every element has been designed with the academic process in mind, from the presentation of the document library to the preferences on offer for saving and managing individual documents.

There's an instant and direct consequence of this: Papers won't be much use to you unless you're an academic. While it could possibly be used for general-purpose PDF management, you'd have to wrestle your way past a lot of features, and wrangle others to meet your needs. It's not worth the hassle. Non-academics simply don't need Papers.

If you are in academia, though, then Papers is just what you need.

It's built around the established patterns of reading and research that you'll already be accustomed to, but does an excellent job of making the whole process that bit easier.

Built-in support for PubMed, EndNote, Bookends and BibDesk is just a starting point. Papers will automatically keep a record of the journal, date, and author of everything you import (if it can find the data) and lets you divide data up into sensible subsets. Authors, for example, can be labeled as Colleagues, Competitors, Coworkers or Friends.

By default your library can be sliced by author, journal, and an iPhoto-like Last Import. And, naturally, you can create your own collections (Smart or otherwise) in playlist-style folders in the sidebar. An unobtrusive tab bar keeps all your current documents within easy reach, without hogging too much screen space.

Papers costs 29 euros (just under $40).

Other options

Cloister by Daniel Cutting is an open source, specialist document manager for those who work with technical papers, particularly with their BibTeX reference data. Papers can do this job too, but Cloister is a completely different kind of app. It's very stripped-down and basic in comparison to the others mentioned here; you can assign documents to groups, and view them in a drawer, and that's about it. But simplicity (and open source) appeals to some people, so you might find it handy to have around.

Document Wallet is more akin to Yep, aimed very squarely at home or office users who need to tidy their lives up a little. Indeed, Document Wallet's selling point is as an electronic replacement for a filing cabinet, and it has been designed to work directly with a scanner. Anything you add to it can be categorized, added to a plain or smart collection, and annotated to a certain extent. There's no built-in viewer, however, so anything you want to see in detail has to be opened up in Preview (or Skim, or any other PDF-aware app).

An Alternative PDF Reader

Skim is a relatively young newcomer, but is nonetheless a very impressive and capable document viewer.

Skim: superb, free PDF reader (Click to enlarge.)

It has been built for people who not only have to gather together a lot of PDFs, but who also have to do a lot of on-screen reading. It offers much that's included in Preview, but a whole lot more besides.

The full-screen reading mode is gorgeous and makes reading long documents much more enjoyable. The configurable Reading Bar adds to the pleasure, highlighting one line at a time to keep your eyes in the right place. The slightly different presentation mode is designed for display of whole pages; full screen mode zooms everything much larger and is for personal reading.

Naturally you can annotate what you read with various sorts of highlight or in-situ sticky notes. Other controls, such as navigation and tool switchers, will be familiar from Preview. Skim, however, makes reading long documents much easier on the eyes and the brain. And since it's free, you have nothing to lose by downloading it.

The Right Tool for the Job

All the apps we've mentioned here have slightly different tool sets and will be suitable for different kinds of users. Papers, Cloister, and Skim will appeal to academics or scientists whose research activities are dependent on PDF files. (DEVONthink will also be of interest, because of its value as a tool for extracting interconnectedness from large collections of data, but that's another issue). Yep and Document Wallet have broader appeal (although even Yep includes a built-in access to Google Scholar). Users with the very simplest of requirements probably won't need one of these PDF-specific tools; their needs will be amply met by simple use of the Finder and Spotlight, or perhaps a general-purpose storage app like Yojimbo or EagleFiler.

Giles Turnbull is a freelance writer and editor. He has been writing on and about the Internet since 1997. He has a web site at

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