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My Paperless Office - One Month Later

A couple of months ago, after reading David Sparks’ Paperless, I started concocting a plan to create a paperless office. If you want the quick version of this story, here it is: It took some elbow grease, money and planning but now I have a workflow that is nothing less than magical.

I started with a large filing cabinet of old papers. Insurance documents, car documents, bills, receipts, health insurance information, and other detritus were cluttering up its many overflowing folders, stuffed into drawers. The filing cabinet weighed a ton and I knew that some very old and unnecessary documents were lurking inside.

The plan was to reduce this mess to something that was simple to maintain, even though it would take no small effort to set up. The resulting workflow had to be backed up, secure and easy because if it took a lot of sweat to get files into the system, I knew it would fall into disuse and eventually abandoned completely.

The parts of the workflow that took shape were these:

  • Document scanner
  • Hazel rules
  • TextExpander
  • Shared folders
  • A Mac Mini
  • Knox
  • CrashPlan
  • Time Capsule

Workflow Overview

The basic idea was to be able to open my Macbook Air at my desk, open my document scanner and send the document digitally to a shared machine. At that point, the file would be appropriately named and filed in a nested folder on a secure (encrypted) drive volume which is then backed up in a verified backup system.

The keys to the system were to be simplicity, portability (using PDF), security (using Knox) and flexibility (using Hazel, shared folders and TextExpander).

The Scanner

For years I’ve procrastinated about creating a paperless office. One of the reasons was that I wasn’t sure of what the best scanner technology was. Buying a scanner is expensive and, if you pick the wrong one, you’re kind of stuck. Putting hours of thought into something that encompassed so many steps was something that was difficult to get my head around.

I decided that the scanner was the first piece of the puzzle I needed to put into place. After a lot of searching Amazon, taking MacSparky’s recommendations into consideration and reading a lot of reviews I decided on the ScanSnap.

The basic functionality, after a few tweaks, is that you open the scanner lid, open the software on your machine, place your documents and hit the glowing blue button. At that point, the document is scanned and OCR’ed and dumped into a directory. It really couldn’t be any easier.

Hazel rules

It’s from this point that Hazel takes over.

I have two sets of Hazel rules. One set is monitoring the Scansnap folder on my Macbook Air and, when a file hits that directory, it bounces it immediately to the Mac Mini server. The other set of rules watch the destination “processing” folder on the Mac Mini and handles naming and “filing” the PDF files when they reach the network folder.

I scan a fairly limited amount of files on a regular basis – electric bills, Internet bill, bank statements, car insurance etc. For each one of these types, I created a rule in Hazel that looks for specific text keywords in the document (supplied via the Scansnap OCR) and then names and moves the document to a nested subfolder like “Car Insurance”.

One thing that it slightly unique with my setup is that these Hazel rules have the keyword “TEXT” in the rule title. This is to designate that this rule is processing the file based on the OCR text content. I also have rules that process files based on keywords in their title, and for these I use the obvious “TITLE” in the Hazel rule to easily find and modify them.

For an in-depth set of suggestions on file name schemes, watch the videos in MacSparky’s Paperless. The upshot of all of this is that, once the files hit the action folder, it gets renamed and bounced to a requisite folder in a matter of seconds.


Sometimes there are one-off files that don’t get picked up by Hazel. This is to be expected but you’d want your paperless system to encompass these files as well so, for these situations, I again look to Hazel and TextExpander.

In this case, I will scan the file and then rename it with a consistent date format, including the category keyword in the title as well. For instance, if I get some supplementary information about car insurance that isn’t a bill, I name the file “2012-08-31 - car insurance supplement.pdf” and the Hazel rule that is scanning by TITLE will find “car insurance” and move the file to the right spot in the Knox volume. It’s a quick and easy workaround to unique files and still preserves most of the automation.

A Mac Mini

The Mac Mini is a fairly new machine that acts as our home server for things like multimedia viewing and music listening etc. Its wired via HDMI directly into our Sony TV. I was a bit skeptical at first as to whether or not it was worth having a pricey machine hanging off of my TV but it has been amazing. I definitely recommend this approach if you’re looking for a good multimedia solution in the living room.


Knox is software by Agilebits which creates an encrypted, secure file volume on your computer. It functions just like a drive when you’re logged into your computer, but if you move the file volume around, it is a completely secure file which is basically impenetrable.

Since I wanted to have an online backup system, it was important to me that whatever got uploaded onto the internet wouldn’t be readable by someone if they were able to hack into the backup cloud servers. Even if they got access, they’d just get a big blob of a file which was completely useless to them.

The encrypted Knox volume gets backed up on a nightly basis. Just to be safe, these files are backed up to my Time Capsule as well.


After doing quite a bit of research, the best online backup system I was able to find that combined simplicity and features was Crashplan.

I don’t really like the interface that much as I find it slightly confusing and inconsistent. The fact that it uses Java is a thorn in my side given Java’s security and speed issues but the good outweighed the bad in this case. I have Crashplan running on the Mac Mini and it uploads the Knox volume on a nightly basis.

Given how important some of these documents are, I think the backup workflow which involves both local and cloud storage of encrypted data is good all around solution.

Caveats and Warnings

You’ll need to keep some documents in paper form and have them handy at all times. For instance, the other day we lost electricity and I needed to call the utility company. Sadly, the bills containing the account number were safely tucked away in a machine which had no power.

It was a wake-up call that I might need to keep a rolling, “latest month” folder of files which get shredded at the end of the month as the new bills show up. I’m not quite sure how I’ll do that yet but, for now, they are collecting dust as an unsightly pile on my desk.

The first thing I did after the power came back on was put all utility account numbers in 1Password. At least that’s one particular problem that won’t happen again.

The Magic

When the system works as I planned it, it is akin to magic. I get the mail, sort it into a pile which gets shredded immediately (credit card applications and such), gets recycled without shredding (circulars, junk mail) and then the bills and bank statements get fed into the scanner one by one.

The files hit the Action folder on the Macbook Air and get whisked away to the shared folder on the Mac Mini where Hazel intercepts them, renames them and files them.

Every day, these files are backed up via Time Capsule and then, several times a week, get backed up to Crashplan offsite.

The total amount of effort to get these documents into my system is the press of one glowing, blue button on the Scansnap. Amazing.