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The Paperless Paradox

Part of Going Paperless Series which provides tips, tools, processes and resources to make the journey to a paperless office or home easier.

“The dream of going paperless has been a pervasive part of our discourse for years but has yet to materialize.” I bet there are at least 50 articles, right now that you can search for in your browser that start that same way. I bet also that each of these articles offers some revolutionary approach, device or software to correct this egregious mistake. And, finally, I bet it works – almost.

So, why aren’t we yet paperless?

I’d like to offer a theory and a possible counterpoint. My theory is simple: paper is cool. It feels good in the hand. A good pen, drawing across the surface of a fine paper is an experience not to be missed. The sound of paper is even cool. Rifle through a few sheets right now. Go ahead. I’ll wait.

You’re back? See – somehow I knew you had some paper. Why? Because its cool. Books are made of paper – lots of paper – and even though digital books are dominating the marketplace, you’d be hard-pressed to deny the feel of an actual hardcover book in your hands. There’s all the tactile and aural pleasures of the book experience, and the ability to flip to any page quickly, and to use two fingers to keep two places in the book, etc.

But before you peg me as a book-lovin’, paper-hoardin’ luddite – allow me to explain a bit more. Its true: I love actual books, but I love my iPad and Kindle too. I sometimes take notes on a pad of paper for speed and convenience but I diligently transcribe them into my trusted system (OmniFocus, if you must know.) I’m down with the digerati. Have been for years. Carried a Newton and a Palm Pilot before my Pocket PC and iPhone. Despite all these things, I still cannot seem to get away from paper. Another bet: you can’t either – not all the way.

So – how do we get out of this paperless paradox? Everyone who is anyone wants to be paperless, but paper persists (for some very good reasons.) We’ve all adopted digital systems but somehow they are insufficient, proprietary, locked up in their own fever-dream of features or hopelessly attempting to emulate, through cheesy graphics, the very aspects of paper we love so much (I’m looking at you, Apple – with the Calendar and Contacts apps. Yuck.)

My approach with technology is simple: do what works, dump what doesn’t, and if I can hold both thoughts in my head at once: continuously refine my systems but stay truthful to my commitments to it. In my downtime, I look for ways to improve how I work, but I never let myself avoid the work itself in the name of a better approach.

The same goes for going paperless. Its naive to think I can just forget about paper. I need to modify my relationship to paper. Paper is hard to eliminate. It is much easier to minimize, process, and just deal with it.

How to Deal with It

Here are the rules I follow:

  1. Choose a Task manager and Note Taking App that will become your trusted system (to use GTD speak). I use  OmniFocus (for Mac users) to track tasks, and EverNote as my note taking app. (There are others, but we’ll come to that.)
  2. Do what you can to minimize proprietary formats. Plain text is best. Exportable RTF is next. Pictures are great, but take up a lot of space. Don’t let yourself get locked into a format if you decide to change systems or want to exchange data.
  3. Scanners are great, but trust me: invest in a smartphone with a really good camera, and if your Task and Note systems have counterparts on your mobile device – get those too. You can’t carry your scanner around with you, and your scanner can’t immediately upload your image into your trusted system.
  4. To-do lists are for verbs, note pads are for nouns (apologies and thanks to Ansel Haliburton on Quora)
  5. All paper items that result in action go into my Task Manager (OmniFocus). All paper items that are to be referenced later, or remembered as information go into my Note Taking app (Evernote)
  6. If a piece of paper is really, really important – I save it. Always good to have a backup of your digital copy. Super-important papers go in a safe.
  7. If a piece of paper is better as its digital counterpart, recycle the original once you are sure your trusted system has got it.
  8. Invest in a portable hard drive and cloud storage for backup. Maybe I should have said that first. I use CrashPlan, iCloud, Amazon S3 and Dropbox. Maybe a bit over-the-top, but I have a lot of data that I adore.
  9. Snap pictures of reference items. Store and create an action item to review (if appropriate).
  10. Only snap pictures of items that drive an action if you cannot translate to a verby phrase easily. What I do is store a picture of a trigger document (or whatever) as an attachment to the action item.
  11. Sometimes, a paper artifact is both something needing action and reference material. In that case, store in the archive, but link to a task with a clear goal.

The best thing about the above rules, is they can be simplified:

  1. Don’t sweat paper too much. If you are reluctant to recycle it, save it.
  2. If it isn’t critical to save, snap a picture and store it in your trusted system.
  3. If a captured item needs action – create a task and link it to your archived image.
  4. Let your system and your method bend and flex a little. Don’t become a zealot.

System in place, and faced with a mountain of paper to process, its easy to backslide. Stick with it. The first weeks are the hardest as you wrap your head around the size of the problem. Or, cut yourself some slack and adopt over time – new items go in the system, old items go in when you find yourself with some extra time.


As mentioned above, I use Evernote and OmniFocus as the cornerstones of my trusted system. These were chosen after a long search for several reasons.

OmniFocus is a Getting Things Done powerhouse, and it plays well with just about every well-designed app on my Mac.

EverNote is a very versatile way to store text (plain and styled), PDFs, images, emails, and lots more. Images and PDFs become searchable, which is what tips it in comparison to other such systems. Searchability is key in a paperless system, especially when everything is a photo, or scane

However: a true productivity and paperless nerd doesn’t quit looking. In another article, I’ll list some of the tools I use to augment my trusted system and how I keep it all linked together.

Good luck going paperless!

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