A few months ago I was given a Doxie Go scanner. I’ve been using it semi-regularly to scan in certain documents and receipts that I want digitized.

At my fingertips were all the tools I needed to set up a clever and usable workflow for a “paperless office,” but it was like having all the pieces to the puzzle without a picture of what the overall end product should look like. I knew that a scanner, an image-to-PDF converter, an OCR app, and some clever folder hierarchy was all necessary, but it all seemed like more trouble than it was worth. Therefore, the majority of the paper documents that came through my home office still get filed away in my physical filing cabinet.

It wasn’t until recently when a comment from David Sparks got me re-motivated to research a better and more consistent way. I had bought David’s ebook, Paperless, back when it first came out in July and I’d read through the first half. But I never made it through to the end which is where he lays out how he actually uses all his tools for his own paperless office. About a month ago I sat down and finished the rest of the book, and upon reading how David actually does things, it all finally clicked for me and I had a clear picture of how to put the puzzle pieces together.

After finishing the book, I spent the better part of my Sunday creating a folder structure on my Mac that mirrored my physical filing cabinet, setting up a few dozen rules in Hazel, and scanning important personal documents as well as all my tax-related documents for this current fiscal year.

Below is an outline of what I’ve set up in hopes that it gives you an idea of how you too can set something like this up. I’m assuming you’re nerdy enough to recognize the tools you may need and you’re clever enough to know how to use them.

• QuickShot iPhone App: I use this iPhone app for saving all my business-related tax-deductible receipts into a folder on my Mac. Since I use my bank statements to manage and balance my books, the receipts themselves only need to stick around in case I get audited or confused about a particular charge.

QuickShot takes a picture and then uploads it to a Dropbox folder of your choosing. I use it to snap a picture of a receipt which then gets saved into my Receipts folder. I can then toss the physical receipt.

Any and all digital receipts I get via email also get saved as PDFs into this same Receipts folder.

• Doxie Go Scanner: This is the scanner I have, and since going paperless it’s proven well for me so far.

For a Paperless Office the Doxie Go has a few downsides: it can only scan one page at a time, it doesn’t scan duplex, and it’s not super fast. For me, this hasn’t been a deal breaker because I’m only dealing with about a dozen documents a week. It takes me just a few minutes to scan them in.

If I was dealing with a multitude of pages on a regular basis, or if I get motivated enough to convert years worth of past documents, then David Sparks recommends the NeatDesk scanner which can handle 50 pages at once, does duplex scanning, and scans documents much quicker than the Doxie Go. (Of course, on the other hand, the NeatDesk is about twice the price of a Doxie Go.)

• Doxie Software: The document importing software that comes with the Doxie Go has proven to be fantastic. Once I’ve scan my documents I import them to my Mac using the Doxie application.

Once imported, I can “staple” multiple scans into a single PDF file (for documents that have front and back sides, and/or are multiple pages), and then save all the scans to my Mac. I use the “Export as B&W PDF with OCR” option — this saves my scans as black and white PDFs with optical character recognition.

Saving the scans as black and white is an easy way to greatly reduce the file size, and I’ve found Doxie’s OCR to be great. All in all I’m very happy with the quality, file size, and searchability of a document once it’s traversed the path from its original physical state to its new digital state.

• Hazel: This was the missing piece for me and this is where the magic happens.

I save all the PDFs from the Doxie into an “Incoming Scans” folder. Against this folder I have about two dozen Hazel rules watching for specific types of documents. These are documents that I commonly deal with, such as:

• Gas, water, electric, and internet utility bills.
• Health insurance notices of benefits received.
• Tax deductible receipts from certain organizations we support regularly.
• Auto and home insurance statements.
• Financial statements.
• Property tax receipts.
• Etc.

What I realized was that each of the above types of documents could easily be identified by my unique account number with each company. And so I set up rules in Hazel to look at the contents of a document, and depending on which criteria that document matches Hazel renames the PDF accordingly and then files it into the proper folder on my Mac.

For example: if the contents of a document contain the words “Gas” and the numbers “555555” then Hazel renames the document to “Gas Utility Bill – 2012-09” and moves it to my “Utility Bills” folder.

To sum up, once I’ve scanned in all my paper documents, I simply save them to my computer and then Hazel takes care of the rest.
For the few documents that don’t match any pre-defined criteria, or for which the OCR wasn’t properly rendered, they simply are left in the “Incoming Scans” folder and I can manually deal with them. I then shred what I don’t need, or if it’s a physical document that’s important to have a physical copy of, I file it away.

This new process makes it far easier to file away documents than my previous way. It’s now a task which can be done almost mindlessly instead of having to remember where each type of document goes in my physical filing cabinet, looking for that file folder, and then stuffing the sheet of paper in.

I wish I would have taken the time to set this up a long time ago. But better late than never. Needless to say, I highly recommend paperlessness.