Planning the War on Paper

As I continue to plan the execution of my New Year’s Resolution to live in a paperless world by the end of 2012, I am faced with a daunting challenge: designing a system capable of accommodating any kind of paper documents thrown at it, or deciding what kinds of documents to exclude, if any.

For a moment I must detour to a conceptual challenge productivity thinkers routinely try to discuss that seems to lack a common vocabulary for the day to day person: the difference between general plans and specific plans. David Allen refers to looking at life from different height viewpoints, such as 50,000 ft. (your largest life-long goals) down to the ground level with specifics (such as “write a letter to my parents”). Somewhere in my journeys I encountered the idea of strategic versus tactical thinking, which is a my vocabulary of choice. Simply defined, “strategy” is a major plan of action such as “use coupons to save money grocery shopping.” A tactic would then be a specific way to implement your strategy, such as “grab the coupons from the newspaper and keep them on a cork board.”

That said, I’ve found an ample amount of resources online for the strategic and tactical planning for my war on paper. I’ve found advice on scanners, the importance of creating backups, and options for general types of software that can help. My research still has one very fatal flaw I haven’t resolved: how I will digitally organize documents at the tactical level.

Strategically, I plan to use one of my favorite services, Dropbox to store all of my scans and make sure they are available anywhere I use a piece of technology. I will likely upgrade from the free 2 gigabytes of storage to the $10 per month plan for 50 gigabytes, which I expect will be enough to hold two years of scanned documents at a time.

What I haven’t had an easy time planning is the devil in the (tactical) details: the digital organization of the documents themselves. What kind of “rules” will I create in order to properly organize documents? This is a very delicate balance: if I have too much planning, the benefits of the system will be overshadowed by the required amount of time necessary to implement it and it will implode under its own weight. Too little structure, and everything will be disorganized, creating a digital mess as opposed to its traditional counterpart.

A few rules I’m currently toying with:

• The top level of Dropbox will contain only folders. No documents should be in that level.
• The second level will be documents specified by year.
• The third level will be grouped by the most specific organization I can classify them to. For example, TV1 Class would be appropriate; “Work” would be too general and therefore prone to disorganization.
• Fourth levels and beyond will be used to house any kind of grouping feasible should more than two different “kinds” of documents. For example, “January’s Meeting” and “February’s Meeting”.

Having the second level of documents be grouped by year has pros and cons. On one hand, its advantageous because it allows me to archive whole years neatly in a way that would be almost impossible without that kind of organization (or extremely time consuming). On the other hand, it will mean that my top level only consists of two folders at a time, which means lots of time wasted just clicking into the correct year. One alternative I am considering involves creating a “Last Year” folder that will be created each January to house all media existing in the Dropbox, while whatever is already in the “Last Year” folder will be downloaded to my main computer and stored locally to save space on Dropbox while maintaining a safe backup.

It has occurred to me that this system will not merely be a collection of scanned documents, but that it must also become a warehouse for all digital documentation: PDFs, Word Documents, Excel Files, Keynote and Powerpoint Presentations, even some video files. I will therefore begin the development of my system not with scanned documents, but with pre-existing digital media.