Digital Decluttering: Detail Work, Final Paper Scans (Premium)

This article series was inspired by our move from a large house into a small apartment and the amount of decluttering we needed to do in its wake. I had thought that I was good at decluttering, but what I came to understand is that what I was really doing—what I was really good at—was organizing the clutter. Sure, I threw stuff away, but I was also hiding clutter and creating the illusion of organization.

This process, very common to those with ADHD, now has a name, “doom pile,” where “doom” stands for “didn’t organize, only moved.” The fallout from this behavior, which I guess I’ve engaged in my entire adult life, is that we had more stuff than we had space for. And so I once again resolved to declutter, this time hopefully more effectively, and whittle down further, so that when we moved again—which we are absolutely going to do—there would be less crap to lug around and store.

When I first wrote about this back in May, I was thinking mostly in terms of physical clutter, as we had moved a disappointing amount of old electronics whose collective fate would be some combination of being recycled, given away, or sold. And I also had an IKEA shelving (or storage) unit with bins, some full of items I use and need regularly, and some filled with items I would need to declutter. Among that latter group was a pile of paper-based photos, documents, newspaper clippings, kids’ drawings, and the like, items I would want to scan in, organize digitally, and then discard.

My wife and I first chipped away at the electronics—it’s still not done, but we made some progress—and then we spent most of July in Mexico. I was ready to start this work as soon as we got home, and I expanded its scope to include the digital declutter of my personal and work archives, which were scattered between OneDrive, my NAS, Google Photos, and elsewhere. What I realized was that I had been making the same clutter organizational mistakes, or doom piling, digitally just as I had been with physical items. That is, my document, photo, and other archives on the NAS and in the cloud had the appearance of being organized, but were not, in fact, organized at all. Ultimately, I decided to start with the digital decluttering and then move on to the paper scanning.

Over the next 5 or 6 weeks, I experienced something very much unexpected. Instead of giving up partway through this work, which seemed inevitable given history and how tedious it can be, I roared through it in an effective and successful manner and completed that work. And given this success I further expanded the scope of this project yet again and decided to fully organize my other digital archives—home videos, music, and videos—rethink my personal and work online accounts, and start researching a new NAS, as mine is old and out of date.

And I finally began scanning the paper-based items that I meant to start with, first by organizing them into logical groups and tossing out those items that I didn’t need to scan. I’ve done this alongside various other tasks, across multiple computers, related to the digital archives as well. For example, I completed the archiving of my music collection, and I then later went through it and removed a lot of duplicate files that I missed (most of which were the same songs in both MP3 and AAC format).

I also found another bin full of 8mm and DV tapes and started re-digitizing the DV tapes so that I could do the same for my home video collection.

And that work has progressed nicely: the DV tapes are now fully re-digitized in raw form, and I’ve started editing them down to “finished” videos that I can archive to multiple places and share with my wife and kids via YouTube. I still need to find a service to digitize the 8mm tapes, as I don’t have a compatible camera, but there are only a few and that should be relatively inexpensive. Once this work is complete, I will declutter all the physical originals, meaning the camera, the tapes, and whatever else was in that bin. We’re not bringing any of that with us on the next move.

All of this work is happening together: the final paper scanning, the various digital decluttering-related tasks, and the online accounts migration work. So there’s a lot going on, and there have been lots of unexpected issues, each of which threatened to, or did for some time, bring everything to a halt.

For example, one laptop recently finished the multi-day task of uploading a copy of my work archive to my Microsoft 365 Business Basic account after several days of failing to do so successfully. Before this, I woke up many mornings to see a red “bang” on the OneDrive for Business icon: The upload halted multiple times over those days because of too-long file paths and a bizarre amount of grunt work to remove unnecessary files that this service does not accept (like the _VTI_* whatever files and folders that frequent legacy IIS-based website folder structures; I had a lot of those).

But I finally got it—I had cleaned up the original archive in tandem—and once I checked that it was complete, I removed OneDrive for Business from that PC and deleted its (duplicate) copy of the archive so I could move on to the next documents archive task.

Which is to make a similar upload to my Google Workspace Drive storage too. And that just started…

This side-by-side work is complex and detail-oriented. And I found myself routinely losing track of what exactly it was that I was doing (or needed to do next) on each of the five or so PCs that were engaged in various activities. And so I finally buckled down and made a master to-do list in Notion.

This list is divided into major groups—Accounts, Personal, Work, Steph (my wife), and New NAS—and then various sub-groups as needed. Each sub-group consists of a series of to-do’s where completed to-do’s are marked as such and in-progress work is colored yellow.  That way I can track what I’m doing and then scan the remaining to-do’s in each list to see what comes next.

For example, though the music collection archiving is “done,” there’s still more work to do. It’s organized, and stored on the NAS, and I did that de-duping work, making it even cleaner and smaller than before. And I uploaded it to my personal Gmail account’s YouTube Music. But I still want to archive a copy of the collection in OneDrive (personal) as well, so that’s on the to-do list.

Also on the music front, and as part of my online account-related activities, I will be moving to my personal Gmail account for YouTube Music and YouTube. Among other things, this will require me to first copy my YouTube Music playlists from my current (Google Workspace) account and make sure they’re all intact. And so I’ve been experimenting with that using various services to find one that works (and, if possible, is free, though it looks like I’ll need to pay given the number of my playlists and the size of some). I’m also thinking about iTunes Match and whether I need to keep that once my music collection is archived in other places. So that decision is on the to-do list as well.

And the paper scanning continues. My wife is away this weekend, so I spent all Friday afternoon on this and then moved the scanner out to the living room so I could keep working on it while watching a movie after dinner, something she would usually frown on. But in her absence, I made tremendous progress and sailed through all the smaller paper and physical items (I scanned some of my wife’s old plaques, graduation tassels, and other things she didn’t want to hold onto physically), leaving behind a much smaller pile of paper documents.

Those I tackled today.

This last pile included old high school newspapers, as I was the paper’s cartoonist. (The principal and vice principals were big fans of my work because I would often include them in the cartoons.) I scanned just those parts of each now-yellowed newspaper and then tossed the rest of it.

I did the same with the Dedham Times issue we had saved from when our son Mark graduated from high school. My baby book, old and stained, and Mark’s “baby’s first year” calendar, which looks brand new.

There were unusual items, like an INFO magazine (for the Amiga) mouse pad with a see-through cover so you could put paper below it; it came with a DeluxePaint III cheat sheet.

But I had my own hand-drawn map of Shadow of the Beast on top of that so I could reference it when I played the game. (Beast was one of the hardest games I’ve ever played and you only got one life, so knowing when and where things happened was key.)

Most of this was straightforward. I bulked scanned items first, usually in JPEG format, and then edited multiple scans in turn while trying to figure out a date for each and add that to the meta-data. Then, I could upload them to the appropriate place(s). For example, those high school newspaper cartoon scans can go directly into my photo collection in the appropriate places in OneDrive and on the NAS, as they each use a date-based folder structure, but they also need to be uploaded to Google Photos. Some items, however, were scanned to PDF because they are actually documents. And those need to be uploaded to our personal document archive. Which is also in multiple places.

Not helping matters, the scanner I’m using, which is part of a fairly recent HP all-in-one printer, is lackluster in some ways, which slows this down. I’ve learned not to trust the closest edge of the flatbed glass, for example, as the scanner seems to ignore the last quarter- or half-inch of that for some reason. And the software, called HP Smart, is anything but: It’s slow and can’t accurately crop individual items, so I need to do that manually.

Among other issues, HP Smart also won’t let me configure a default format (JPEG), so I have to change that on almost every scan before saving. And because it’s a badly written “modern” app, it doesn’t support tabbing between controls with the keyboard, which forces me to use the mouse, slowing me down. I can’t wait to never use this again.

And some scanning required a bit more work still. There were several instances in which I had to stitch multiple scans into a single image because the flatbed wasn’t big enough to scan something all at once. I did the stitch/merge work with Photoshop Elements—it has a nice “guided” feature for that—and then cropped them in Paint.

All that adds up to the obvious news that scanning paper, editing the resulting digital file, and then archiving it—in my case, to multiple places—is slow and tedious. It is exactly what you think it is.

But it can also be fulfilling. I know this is scary to some people, but I get a real thrill or sense of accomplishment when I throw away the originals, and that’s true whether it’s paper-based photos, old newspapers, kids’ drawings, or even baby books. (I did ask my son if he wanted his “baby’s first year” calendar first). As the pile of completed scans grew and the piles of scans to-do shrunk, I could feel that same sense of purpose that earlier drove me to complete the digital documents and photos archiving. Success breeds success. Sometimes it just happens a little more slowly.

As I write this, I’m almost done with the scanning. As noted, my wife is away this weekend, so I expect to finish that today and then finish editing and archiving the files by the end of the weekend. All while working on that master to-do list and making progress where possible on the remainder of these tasks. (And, what the heck, writing about it for this article.)

Next, I will write about my work migrating online accounts, which is itself a scary and detail-oriented task that encompasses numerous online services and many gigabytes of data. I’ve had some half-steps backward here and there, but it’s all coming together.

More soon.