I’ve been a big fan of the journey (you never quite get there) towards the paperless office for years, since I first bought a Fujitsu ScanSnap scanner. It’s a terrific device; you drop one or more sheets into its hopper, press the button on the front, and it scans both sides of each piece of paper and turns them into a PDF. I use it with Acrobat Pro, and take advantage of a nice AppleScript that Joe Kissell created for his book Take Control of Your Paperless Office (it’s a good book; you should buy it). The script uses a Folder Action to automatically fire off Acrobat’s Optical Character Recognition, so the scan gets turned into copyable, searchable, indexable text. After the paper goes through the scanner and becomes a PDF, I shred it. I try to only keep the paper that you must have around (important legal documents, for example) and those live in a fireproof lockbox.

Organizing the files

When you have so many documents, you want some way of organizing them. When I bought the ScanSnap, I also bought Yep, from Ironic Software. It’s designed to manage, organize, and retrieve PDFs, and you don’t have to copy PDFs into a central database. You can use it to add tags to your documents and search them. It was just what I wanted. I’ve added a couple of thousand documents to Yep and tagged them (bills, contracts, statements, etc.). Then Ironic came out with Yep 2. I considered upgrading, but the new version didn’t seem to have enough compelling features (the company didn’t help matters by failing to put up a clear page explaining the differences for their existing customers). And now, many other Yep users are complaining that Yep 2 seems to be moribund, with no updates for more than a year. Yep 1 isn’t working correctly anymore; the tagging is messed up and I can’t fix it. So I’m in the market for a new organization tool. I’m resigned to retagging everything, though it will take a long time. A program with the concept of tag groups would be helpful (so I could apply multiple tags at once).

The tools I’ve been thinking of are:

• Evernote Premium
• Paperless, by Mariner Software
• Devonthink Professional, by Devon Technologies

I’m already using Evernote for general notes and snippets, so I’m strongly considering upgrading to Evernote Premium ($45/year) and using that; I’d just dump all of the already scanned PDFs into it. But I have some concerns. First, the info I’ve been scanning isn’t exactly secret, but it is sensitive (bills, personal data). The idea of putting that into the cloud makes me uneasy. Second, Evernote doesn’t appear to have great options for getting information out once it goes in. I’d have to retag all of those documents, which would be a drag. And I use the Evernote iOS apps, and were one of those devices lost or stolen, I’d hate to have all that personal data exposed with it.

I know the least about Paperless. It’s reasonably priced ($50). It appears to have pretty much the same feature set as Yep, plus modern and expected additions like Smart Collections. I’d have to retag my documents, but don’t know how easy that would be. Anyone have experience with this program? Update: Paperless clearly isn’t going to meet my needs, so it’s off the list. Tried it, hated it, deleted it.

Some people swear by Devonthink ($80). It seems fairly complicated to learn and use. The company touts their AI that does automatic classification and grouping. But is that smart enough so that I wouldn’t have to retag every file manually?

As you can see, I’m most interested in reducing the labor in retagging files. And now that I need to migrate to a new program, I want to be able to maintain my time investment if I have to do it again in the future (sadly, no software is forever).

I’m sure that people I know have solved this problem for themselves. Can you help me solve it? I’m open to the programs above, or others. The restriction is that it has to be a Mac, program, of course. I’ve previously used Yojimbo, but migrated to Evernote.

We’re making the trek to San Francisco this week for Macworld Expo; it’ll be my 26th SF Expo (yep, I’ve been to them all).

We’ll be at the show from Wednesday through Friday. Specific events:

On Thursday, I’ll be leading a BOF (Birds Of a Feather) discussion:

Building Your Home Media Center
January 27, 2011, 5:30 PM – 6:30 PM
A flurry of hardware and software solutions have hit the market to get video and audio media into your living room and onto your iOS devices. Apple TV, Plex, Boxee, and many others are competing for your attention and dollars. In this discussion, we’ll share the best ways to put together a home media center that works for you.

On Friday, Dori will be presenting one of the User Conference sessions:

Mobilizing Your Web Site
January 28, 2011, 1:00 PM – 2:15 PM
As a web designer, you used to be able to assume that everyone had at least a certain size display. But now many of your site’s visitors arrive via iPhones and iPads, and to support them you’ll have to re-do or duplicate your entire site – or do you?

No, you don’t have to create an entirely new site for mobile devices, or rework everything for the lowest common denominator, or even remove all your image rollovers.

In this session, you’ll learn what you need to know: not just to make your sites work well and look good, but also how to enhance sites to take advantage of the functionality that Apple built into Safari for the iPhone and iPad.

We’ll see you at the show!