Last August, my wife and I decided to downsize our home situation moving from a 1500 square foot home, into a 500 square foot studio apartment.

That’s right… we moved into a home that was a third the size of what we were used to.

The reasoning behind this decision is worthy of another post entirely, but one of the results of this move was the act of us digitizing our entertainment, as well attaining a paperless lifestyle.

It certainly wasn’t easy and like all expected challenges in my/our life, I had to have a plan of attack from the outset. First and foremost we needed get rid of a lot of stuff! Physical CD’s, DVD’s and books take up a lot of space in your home (whether you notice it or not) and our new tiny apartment simply wasn’t going to have the room to house everything we collected over the years. So it didn’t take long before I decided that anything that could be transferred to a hard drive or cloud-based storage, would be.

Sounds simple enough right? It is actually. But, another problem reared its ugly head. After ripping and selling all of our music and DVD’s over the years, I knew immediately that this process would take time, and lots of it.

The good news though? It’s totally worth it. The even better news? There are a lot of ingenious services out there that will help make the process much, much easier. So I thought I’d share my findings with you all.

Entertainment…

With the advent of cloud-based services like iTunes Match and the low price points of external storage nowadays, it’s simple (and relatively cheap) to come up with digital backups of your entire entertainment library. I ended up subscribing to iTunes Match, transferring my entire music library there and buying a USB hard-drive cradle like this one for everything that Match wouldn’t cater to. By the way, if you have a lot of old hard drives laying around, this cradle is awesome, as it caters to both desktop and laptop drives.

On the software end, to rip our CD’s I’d used iTunes over the years and for the DVD’s, I used RipIt. Both apps are incredibly easy to use and I never ran into copywrite issues ripping the DVD’s either. Please note that the time this takes has EVERYTHING to do with the speed of your CD/DVD drive. I think collectively, I was at it for about a week, just evenings though. It’s boring “work” and you should find something to do between rips. As I mentioned, we were moving so I had plenty to do.

Once everything was ripped, I sold all of the physical copies on Craig’s List or gave them to friends and family. And no, that wasn’t easy.

The Dead Tree Stuff…

So, that obstacle behind me, I moved on to everything else. It didn’t take long at all to realize that digitizing your music and movie collection is dead simple compared to digitizing all of the paper that’s been in your life.

Next I dealt with the books.  The books weren’t that big of a deal. We basically kept our treasured copies (the ones you read more than once, or the ones that changed your life) and got rid of, or sold, the ones that were literally collecting dust. Then, after you have done that bit of curation, you look at the remaining stuff and see if it’s worth buying their e-book counterparts. It’s surprising how this simple process whittles down the bulk of your book collection. I am not going to lie, if you love books, this process is really hard to go through. Prepare yourself and steel your resolve. You can do it!

In the end, we sold the bulk of our book collection to used book stores around the area, but another great find was donating the rest to charity programs that routed your books to other countries or even prisons. If you have books after this process (I had an old HTML 3 book the no one wanted, can’t blame them either), at the very worst you should be able to recycle whatever is left.

Once the books were gone, we felt like we were really making progress! The house we were selling suddenly seemed downright cavernous! We were well on our way! But then we started opening our closets and saw all the white file boxes with Sharpie-scrawled years on them.

The Rest…

What was in these boxes were all of the documents we’d collected over the years. It was either important stuff (like tax info) or things that we thought we might need in a pinch (like service manuals for your vacuum). There was a lot of crap too that we simply didn’t need at all: it would all have to get recycled.

When it was all there, sitting out in front of us, it was intimidating thinking about everything we were going to have to do to make this work. But you start simple and go from there. We started the process by going through everything quickly, separating everything into two basic piles: the stuff we planned on keeping and the stuff we were going to shred and recycle. After that was done, it seemed a little more manageable which was great psychological booster. I went ahead shredded everything we were going to recycle and brought it in bags to the local recycling center. We actually used some of it for packing material too!

At this point in the process, we had gotten rid of about 60% of it all. It was time to digitize the rest!

How We Did It

First things first: move to paperless billing. Log into the respective site of any of your monthly bills, or give them a call and make that switch. Almost every service offers it now.  Just bite the bullet and make the change, I think you’ll find the adjustment period very short. :)

You also need to realize that you are not the first person who has done this. Today, there are TONS of resources out there. But if I had offer one to you? I’d recommend this: “Paperless Field Guide” by David Sparks.

This book is invaluable in breaking down the process of creating a paperless, workflow-based system in your life that is not only space-saving (physically and digitally), but is also immensely useful and reliable going forward. Sparks offers great hardware and software suggestions and his writing and overall approach to the subject matter is very accessible and not overwhelming in the slightest. He also offers excellent examples and though I found Sparks’ personal workflow system a bit overkill for me (he’s a lawyer, so it kind of needs to be), I ended up with my own, much simpler workflow; borrowing a lot of best practices from the book and adapting it to my life.

That’s what is so great about this book! It isn’t a blue print for what you need to do, it’s merely a guide.

Here is my paperless workflow, in a very barebones format:

  1. Find, or receive, a piece of information that’s worth keeping forever.
  2. Scan this document somehow (more on this below) into a PDF document, preferably with OCR (again, more on that below).
  3. Move this document into a predefined folder structure that’s easy to navigate through, with a predefined title structure. I went with “year_date_description” (i.e. “2013_0410_utility_bill”).
  4. Verify everything saved properly and get on with your life.

Sounds simple right? Well, it is, but not until you get a hold of the right tools.

What We Ended Up Using…

A Document Scanner of Some Kind: This is pretty crucial and, luckily, there are a TON of options out there. We bought an HP Scanner/Printer combo a long time ago for $50, so we used that. It doesn’t have to scan spectacularly, but it definitely should scan documents so that they are highly legible. The faster it scans, the more time you will save.

PDFScanner: This software works incredibly well with any scanner you plug into your Mac and, compared to it’s competition, it is very low-priced at just shy of $15. Just turn your scanner on, launch “PDFScanner”, click the “Scan” button”. That’s it! It will take your paper document and create a PDF out of it in no time.

Other things this software can do that are pretty invaluable are OCR - Optical Character Recognition as well as preset naming conventions (if you want the date it was scanned, inserted in front of the title every time you scan a document for instance). Both of these features are key, if you are trying to organize your documents so that they are easily searchable. “PDFScanner” can also mimic duplex printing as well, which is nice when you have a multi-page document that you want to transfer into one multi-page PDF document.

I was initially skeptical at the price, and while it’s more expensive counterparts can in fact do more, this software catered to my needs/paperless workflow nicely! I used it to scan literally everything we had left on file (read: 100’s of documents).

Dropbox: There are a ton of online cloud storage solutions out there. I use Dropbox because it’s flexible and I am already familiar with how it works. If you go with another one, make sure the service you choose supports folder structures. Most of them do nowadays, but I thought I’d throw that out there. PDF’s don’t take up much space, so I have been working with a free Dropbox account at the moment. I haven’t even come close to my 5gig limit, you/I can always pay for more storage if you run out.

JotNotPro: Mentioned in the “Paperless: Field Guide”, this is my mobile “Plan B”, for when I am not going to be near my home scanner anytime soon, or if I am just being plain old lazy. It’s an iOS app that you use to snap a picture of your document and then it automatically turns the pic into a pdf for you to send where ever you’d like. You can also link this app to automatically upload to a location on Dropbox as well, which made it no-brainer for me.

There’s a free version of this app that might suit you just fine, but I ponied up a couple of bucks for the Pro version. It provides extra functionality and it’s just a great app, so I wanted to support the developers.

Evernote: I’ve mentioned Evernote several times on this site. No bones, I love it. But as far as my paperless workflow is concerned, I use this only to file non-paper based things, like prescription and insurance cards, my license, my passport… you know, the important stuff that you need to literally have at your fingertips, tagged and in full color.

A lot of people use Evernote as their complete paperless eco-system/workflow. I didn’t only because I use Evernote for a lot of other digital-memory-based systems in my life and didn’t want my important/crucial documents getting buried in all of that. If this fits the bill for you though, go for it. You can’t beat free and their mobile apps are second to none.

Worth the Time and the Effort.

Whether your life necessitates it or not, digitizing your entertainment and important life documents, as time-consuming as it was initially, was an incredibly smart move for us. I no longer have to drag boxes out and leaf through a ton of folders to find my insurance info, past salary amounts or my tax info from five years ago. Now that it’s organized and searchable, I can find pretty much anything in a matter of minutes (at home, or on my phone even). That’s pretty incredible when you think about it!

Developing a good workflow makes this task WAY less arduous and having the right tools (hardware and software) can automate scanning and filing into a process that takes less than ten minutes out of your day.

The minute you need it and you see, firsthand, how much your hard work paid off?  I tell you, it really is a thing of beauty. And seeing all of that extra closet space you just regained?

Well, that’s pretty awesome too! :)