What I Use: File Management (Premium)

My approach to file management has evolved over the years, guided by both my own special form of OCD and by major improvements to cloud-based storage services.

And to be clear, I don’t necessarily think that my system is what you should do. I have my own peculiarities, including some need to be organized and to keep everything I’ve written. Your job may be very different, as may the types of files you want to keep. In fact, I fully expect that many people will try to make sense of my system and wonder what the heck is wrong with me.

So the only goal here really is to explain what I do and, in doing so, inspire you to think about your own needs and perhaps make changes so that your own file management methods become more useful to you. (Or maybe you’ll realize that what you’re doing now is just fine, thank you very much.)

Without getting into the historical stuff too much, I used to organize my work-related data in an overly-hierarchical and organized way that I’m now embarrassed by because it is so unscalable. But any time I want to be bothered by it, I can still see my old filing system as it’s backed up on my home-based NAS and in OneDrive in the cloud.

In this system, I organized by topic and then by date. Top-level topics included such things as Office Windows, Windows Phone, Xbox, and so on. And within each of those folders were folders for years (2009, 2010, and so on), and inside of those were folders for individual articles, and those folders were named like 2011-01-06 – Microsoft at 2011 CES so that they would be arranged by date as well.

That system was top-heavy and, in retrospect, inefficient, but I think what really killed it was that search got really good. Instead of navigating into a folder structure to find something based on where I figured it must be, I could—and now do—simply search for some keyword in either the filename or content of the document in question and I can find it very easily. (Go figure, but this is faster on OneDrive than it is with the NAS.)

Anyway, at some point, I decided to move away from my old system, and I started implementing the first versions of what is my current system. And that point was sometime in 2012, based on what I can see in that old folder structure, since I gave up organizing things as I had been doing and started a new folder called Blog Posts and News. In this folder, I segregated out the lighter day-to-day stuff because, let’s face it, the chances of me needing to reference such things internally (as opposed to searching my own site on the web) was/is remote.

But over time, that became my current system, or at least the basis of it. That is, with some article series-based exceptions I’ll discuss later, most of my day-to-day writing is now organized more simply than before.

So let me step through a basic workflow.

Let’s say it’s Monday morning and I’m writing some news article; the topic doesn’t matter. I write this article in Word, save it to the Desktop, as usual—I have configured Word to save to the Desktop folder by default—-and either do or do not find and then edit an accompanying image, which is likewise saved to the desktop, both in original and edited forms. When I’m done with this article, it’s time to file it and whatever image(s) I’ve created/edited and any other related files that are sitting on the Desktop. Where do they go?

In OneDrive, I’ve created a simple folder structure under the top-level Documents folder that has _old, Book, Home Swap, Notebooks, Work, and Work archive folders. Most of these don’t matter day-to-day, but I assume by the names that most are at least semi-obvious. The one that matters most to this discussion is Work.

The Work folder contains several folders, one of which, _Promo graphics to use, I may retire soon since I almost never use it. (It stores images I may want to use in later articles, for the most part.) Among the other folders is To-do, which holds ongoing articles and article series, review templates, and the like, and I sync this folder to every single PC I use. And then the center of my latest organizational system, several date-based folders, each of which corresponds to a particular month.

There are some important things to know about this folder and those date-based folders it contains.

First, I pin two folders to the Quick access area in the navigation bar in File Explorer, which you can see in all of the screenshots here so far: To-do and whichever folder represents the current month (2021-01 as I write this).

Second, everything I write for work will eventually be put into one of the date-based folders. That file I wrote on that Monday morning and its accompanying graphics and other files will be dragged from the desktop and filed away (in 2021-01 in this case). That’s where they’ll always live, mixed in with everything else I wrote that month, and if I need to find something, search will make it happen.

Third, this requires a bit of organizational work at the beginning of every month, but also at the beginning of every half-year (or maybe quarter). Since we just entered a new year, I can explain what that means by explaining what I did.

There are usually 6-9 date-based folders in Work, and if you look in the screenshot above, you’ll see there are currently 9, with names like 2020-10 (for October 2020) through 2021-06 (for June 2021). When the date shifted over to 2021 this past Friday, I did the following:

• I created empty folders for the first 6 months of 2021 so that I can access them from File Explorer. This can happen in File Explorer or on the web.
• I unpinned 2020-12 from Quick access in File Explorer and pinned 2021-01 so that all new documents and other files go in the right folder. (If this month wasn’t the start of a new year or half-year, this is the only step I’d need to take.)
• I moved three previous folders—2020-07, 2020-08, and 2020-09—out of Work because they are now out-of-date and it’s unlikely I’d ever need to access them directly, plus I don’t want them piling up. Where do I move them? There is also a Work archive folder under Documents in OneDrive, and this folder contains year-based folders (2012, 2013, and so on), and then the respective month-based folders inside of each. They’re there if I ever need them. (I rarely do.)

While I sync To-do (and usually Book, which contains the Windows 10 Field Guide files) to the PCs I use, I never sync the month-based folders (like this month’s 2021-01), because I don’t have to: I’m just filing things away there, usually from the desktop. If I need to access something there from another PC, it’s still there, in that OneDrive will show the files and let me download on the fly.

What this means in the real world is that when I bring a new PC online, I wait for OneDrive to sync the placeholders for all of my content. When that’s done, I pin To-do and the current month folder (2021-01 today) and probably Book to Quick access in File Explorer. And then I sync the contents of To-do and Book so that they are available offline.

My To-do and Book folders are both a bit over 700 MB in size, so syncing these two folders takes up less than 1.5 GB of disk space. This speaks to an interesting trend in this new age of computing, where the internal specs of PCs have improved dramatically and it’s possible to get an Ultrabook with a 2 TB NVMe-based SSD now if you want or need such a thing. But as a writer who creates relatively small files—compared to, say, a video editor, perhaps—I have no need for such a thing. And while it’s actually getting hard to find PCs with 128 GB SSDs, I would absolutely be fine with such a thing.

But that’s me. Again, everyone’s needs are different. At the very least, learn this from my madness: You should always do what makes the most sense for/to you.