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The World’s Easiest, Most Awesome, Hands Off, Set and Forget, Document Management System (Mac)

Paperless filing system

If you have a paperless filing system, wouldn’t it be nice if you could drop a bill into your scanner, and have it automatically scanned, renamed, and filed in the proper place on your computer, with no effort on your part? And wouldn’t it be nice if you could have access to that document from any computer, with minimal security worries? With a combination of two programs on the Mac, you can do all of that.

My journey into the world of a paperless filing system has had a few twists and turns. For a few years, I used Evernote. I would scan all of my bills and other documents into Evernote, then name and tag them. Evernote gave me the benefit of having my documents available from everywhere. I never felt too comfortable with that system, though, since my data wasn’t encrypted on the Evernote servers. It also required enough effort that I often had a big stack of documents sitting on my desk that needed to be scanned.

Next up was DEVONthink, a Mac-only document management program. DEVONthink is immensely powerful, and got me part way to the automated filing of documents, but I still had to name all of my documents after scanning. DEVONthink also doesn’t make remote access too easy.


The System

Then I heard about a system discussed on one of my favorite podcasts, the Mac Power Users podcast. I was intrigued. One of the hosts, David Sparks, talked about how he used Hazel to automate his filing system. Hazel is an app that monitors folders, and can perform a variety of actions on files that show up in those monitored folders. I already owned Hazel, so I thought I’d give it a try. His system involved having all documents get scanned as PDF files into a Hazel-monitored folder. Hazel would analyze those files, rename them, and move them to an appropriate folder.

I gave it a try with a big pile of documents that were overdue for scanning, and in about an hour I had a dozen Hazel rules set up to automate my paperless system. Goodbye Evernote and DEVONthink, at least as filing tools. I sat back and watched in amazement as the only step required of me was to put a document into my scanner and hit the Scan button. Everything else was automated. One big caveat – this system assumes that your scanner comes with software that provides OCR (optical character recognition), or that you otherwise have access to OCR software. Without it, Hazel can’t analyze the contents of scanned documents.

Here is a screenshot of a sample rule I’m using in Hazel.

Hazel paperless filing rule

This rule looks for documents in my watched folder that contain my electric bill account number, and the word “Electric Utilities” (which shows up on all of my electric bills). Any document that meets those parameters is renamed (more on that below), moved to a subfolder of my “Electric bill” folder, and marked with the color red. The subfolder is based on the year of the bill, so within the “Electric bill” folder is a “2012” folder.

The Rename function can be examined more closely. Here is that line, expanded:

Hazel automated filing rule naming convention

I’ve modified the “date added” element so that it only appends the year and month, since I just get one bill a month from the electric company. This is a tweak I picked up from David Sparks’ Paperless iBook. At the bottom of the screenshot above, you can see a sample title. Since I scan to PDF, the “.xxx” would be “.pdf” after the renaming.

Since I use one of CrashPlan’s paid plan as part of my backup system, my documents are all available online, too. My understanding of CrashPlan is that your data is encrypted locally before being sent to the CrashPlan servers, so I feel better about having my data in the cloud than I did with Evernote.



I see three benefits to my new system. First, it is frictionless. This is the most important factor to me. I don’t have time to sit down and name, tag, and manually file documents. Second, it is nonproprietary. If Evernote or DEVONthink had ever gone away, it would have been a real hassle to me to move my data. And with the search power available on computers now, I’m not losing much by not using a dedicated document management app. Third, I have secure access to my documents. A concern over security is why I moved away from Evernote for document management purposes.



There are some limitations to the system. First, the “hands off” aspect of it doesn’t work for all documents. It works for documents, such as bills, that you get on a regular basis. But those random one-off documents that we all receive have to be handled manually. Another limitation has to do with the naming of documents. The system will name the document with the date or month when you scanned the document. So, if you fall behind in your scanning, your documents won’t have the right date unless you manually change the date.


Room For Growth

There are a few tweaks I’m looking into as well. As noted above, I’ve purchased David Sparks’ Paperless book on the iBook Store, and highly recommend it even from the little I’ve read so far. I’m not too far into it, but I jumped ahead to see that he does go through his system in more detail than I’ve covered here, complete with video. I’m anxious to keep reading, and see what other ninja tricks he uses. He does mention something about tagging, which I need to read more closely, as my current system is purely folder based.

I also would like to try to set up Hazel so that I can drop a document into Dropbox from any computer, and have Hazel grab that document and move it into my main folder for processing. That would allow me to manage my bills away from home.


I never thought I’d be excited over a filing system, but I really am psyched about the possibilities of this system. Do you have a favorite system that you use? If so, let us know in the comments.