Digital Decluttering: Some Photo Progress, and a Shift to Documents (Premium)

Two weeks ago, I started the time-consuming process of organizing, tagging, and archiving over 21 GB of scanned photos as part of a new digital decluttering initiative. Today, I am happy to report that I’ve concluded that work, and less happy to report that I still have a lot more work to do. So I will shift gears a bit and move into a new phase of this process related to similarly organizing and archiving my documents and other files. This one, alas, is a challenge of a different kind because there is so much more of it.

As noted in Digital Decluttering: Finishing the Job (Premium) and/or Digital Decluttering: Back in the Saddle Again (Premium), I have several buckets of physical and digital clutter that I would like to make progress on this year. (It’s unreasonable to think that I can get through all of this in 2023, but I will try with the understanding that my energies get divided over time and that I should do as much as possible when I’m so inspired.) They are:

Electronics and other physical items. We moved from a very large house to a very small apartment this past year and did a lot of downsizing, but there is more work to be done. In particular, I have a lot of aging electronics to deal with still, many of which are just stacked up in the corner of our dining room right now. This is something I’m working on with my wife.

Paper-based photos and other documents. I have at least one bin in my storage shelf that is full of stray photos, documents, newspaper clippings, kids’ drawings, and more, just sitting there in a pile. I will sort through these and scan the items I want to keep digitally using a flatbed scanner. Originally, I thought that I’d do this work first, but I ended up going through my unsorted digital photos and scans instead.

Document archive. My (mostly work-related) documents archive is stored in OneDrive, and while much of it is nicely organized (more on this below), there are lots of unsorted documents and folders in there and I want to do a pass at removing unnecessary items and duplicates, and at truly organizing it once and for all, because cloud storage is a finite resource that I pay for. Tied to this, I have a copy of much of this (the archive parts, basically) on my NAS, which had been offline since the move, until yesterday. Again, more on this below.

Photo collection. My (by which I mean my wife and I’s, or perhaps my family’s) photo collection is stored in OneDrive, where it is mostly organized in date-based folders (especially the pre-smartphone stuff), in Google Photos (which I consider my primary collection), and on the NAS. I’m mostly OK with this system, but the work I just completed (more on this below) was to collect all of the unsorted photos and scans in OneDrive, take them offline, sort through them, organize and tag them, put them where they belong in OneDrive (in whatever date-based folders), and then archive them to Google Photos as well.

NAS. So I have this NAS. It’s been offline since the move. It has its own versions of my document archive, my digital photo collection, my archived music collection (CD rips and digital purchases, also in iTunes Match for now), and some videos (both home movies and a mix of TV shows and movies ripped from DVDs and Blu-Rays or purchased digitally; the latter are not archived anywhere else because they take up a lot of space and are not essential). Much of it is organized well enough, but the documents bit is problematic.

That’s a lot of stuff. But I have made some headway: over the past two weeks, I completed the process of organizing, tagging, and archiving over 21 GB of loose digital and scanned OneDrive-based photos. This was both tedious and interesting in that some of the work was quite forensic in nature because many of the photos lacked any date or other context. And so I approached this task as logically as possible, starting with the low-hanging fruit, so to speak, those photos or loose scans where the date was obvious. In those cases, I simply tagged each file with the correct date, moved them in my OneDrive date-based folder structure accordingly, and then copied them to Google Photos using drag-and-drop into the browser.

Many files required more work. Some of this was just time-intensive and some required investigation.

On the former front, I had over a dozen files of travel-related scans, meaning tickets and similar items from trips. There were Paris Metro tickets, tickets for museums and events, and so on, with several separate items per file.

I tried automated tools for separating these items from the original scans—Adobe Photoshop Elements offers such a tool, called “Divide Scanned Photos”—but none worked well, with incorrect cropping.

And so that work was manual, time-consuming but easy. These scans included items from 2006, 2007, 2008, and 2010 trips to Paris, our one trip to Rome, one of our home swaps in Amsterdam, and some random sports tickets and whatnot.

Many of the scans were difficult to place. I had a set of scans of my wife’s family’s photos, pictures of her, her family, and her friends from long ago, plus some scanned report cards and notes, and so she helped me with those of course. Multiple pictures of the kids, like official school photos, some dated and many not, and so I simply compared the relative ages of them in each and ordered them accordingly, and I’m pretty sure those are all 100 percent correct from a (yearly) date perspective. I do at least know my own kids well.

And then there were the vaguer ones. A lot of them. I had a very large set of loose scans from my own family’s photo collection, some in folders like “1970s,” “1980s,” “1978 probably,” and so on. And I did similar comparative work with those, albeit less accurately, to get them organized as well as is now possible.

The date stuff is interesting. Imagine a set of photos of my family from the 1970s. I can tell it’s Easter, or Christmas, or someone’s birthday, and after comparing them with photos plus or minus a few years, I think I’ve figured out which year they’re from exactly. I would Google things like “When was Easter in 1978,” and then date those photos accordingly. (I did a lot of date Googling.) For vaguer photos, like a set of beach shots that I knew were in that year but didn’t know the exact date, I would just tag them with a date like 7/15/1978. I moved from specific event dates to less specific event dates, saving the hardest ones for last.

And I got through it. Is it 100 percent correct? No, of course not. But now the photos are at least sorted, and most are correct, with many of the scans being correct enough. They’re all in OneDrive, organized in those date-based folders, and in Google Photos. I feel good about it. (Indeed, I’m surprised I got through it all.) But again, this is the tip of the iceberg. And so I needed to move on to a new digital decluttering task.

As I did this work, there was one thing nagging at the back of my brain, the NAS. When we moved to the apartment, I took the NAS with us, but I didn’t turn it on because I was out of electrical sockets on the surge protector in my little office nook, and worried about overloading a single circuit, I left it sitting there offline. I knew I had lots of stuff on there, and probably lots of loose photos and scans. Indeed, I was pretty sure I had a duplicate of the collection I had just organized and finished with. But … did I have more on there? Were there other collections of unsorted photos on the NAS?

I had to know. And so I connected the NAS, temporarily, by plugging it in across from my desk and running an Ethernet cable between it and the switch next to my desk. And then I connected to it for the first time in five months.

What I found, photo-wise, was a bit deflating. In addition to the unsorted photos and scans I had in OneDrive—there were indeed duplicated on the NAS—I found a total of almost 100 GB of additional unsorted photos (!), spread over many, many years. (Excluding the parts I’m reasonably sure are just duplicates, it’s still about 95 GB. But I still need to go through it all.) Much of this stuff is absolutely in my organized photo collections in OneDrive and Google Photos, thankfully. But some of it is not, as I confirmed in a quick pass through the folders. This will require work. And time. And I was ready to do something different for a while instead.

Before getting to that, it’s worth pointing out that this NAS is no longer supported by WD. I purchased it back in 2015 after considering the PC backup strategies of that time, and it’s mostly served me well, though it’s always been a little slow. I have at different times considered not bothering with a NAS anymore, and had researched whether there were simple USB-attached external hard drive solutions that supported RAID 1/disk mirroring for failover in the event of a drive failure. But as I considered this NAS during the photo/scan organization tasks of the past few weeks, I did a bit of research on modern NASs, and it’s possible I’ll get a new two-drive Synology NAS or similar to replace my little NAS after all this work is done. For now, I just want to get organized.

Looking at the other data on the NAS, I found my work archive, which is divided into two eras. These can be defined as “the way I used to organize this content” and “the way I now organize this content.” And while I know I’ve written about this before, it’s probably worth stepping back a bit and considering this. Not because I think that everyone should do what I do, hardly, but it’s one way. And you can likely learn from it either way. Maybe it will be a lesson in what not to do.

My initial organizational structure was based on topics. And from a work perspective, the root folder was eventually renamed to “Penton,” as it encompassed everything I wrote for the SuperSite for Windows and my employer’s related publications. This folder contains folders for things like receipts (for expenses), royalties, my hiring information, and so on, but also publication-based folders for blog posts and news articles, “CHEX” (Connected Home Magazine), “SuperSite” (The SuperSite for Windows), “UPDATE” (what was eventually called Windows IT Pro UPDATE, a weekly email newsletter that was our biggest and first, and thus called “Mother UPDATE” internally), and “WinMag” (which contains my editorials, reviews, and other articles from our print magazine, which was called Windows NT Magazine when I arrived on the scene in 1999 and then, after several name changes, Windows IT Pro Magazine).

This is “organized,” but it is not a good organizational system.

That “SuperSite” folder became a dumping ground for anything and everything that wasn’t specifically non-SuperSite articles and other writings. It’s where everything is, my entire work archive—interviews, leaks, private emails, whatever—and it’s big. The “Penton” folder is about 166 GB in size, for example, but the “SuperSite” folder is 165 GB of that. (The other folders are almost literally all Word documents.) There is a lot there. But it’s worse than that.

Looking inside “SuperSite,” there are folders for “_Windows,” (the “_” bit is so it appears at the top alphabetically since I used that one the most), “_Windows Phone,” “_Xbox,” “Amazon,” “Apple,” “Google,” and “Other.” And inside of each of those folders, I finally moved to a date-based folder structure. In that Google folder, for example, there are folders like “2007-11-03 – Gmail IMAP,” “2008-09-02 – Google Chrome Beta,” and so on. But the “_Windows” folder. My God, the “_Windows” folder. This became my core archive, and it is organized just like my OneDrive-based photo collection. Because of course it is. There are year-based folders (“1995,” “1996,” through “2011,” plus an “Old” folder), each of which contains date-based folders like “980818 NT 5.0 Technical Workshop,” “2005-01-01 – MSN Music review,” and so on. Many of these year-based folders have hundreds and hundreds of sub-folders. There are 260 in 2005, for example, and 209 in 2006.

And I have to go through them. Why? Because this “SuperSite” folder somehow takes up 165 GB of space. And that means that’s not just Word and text files in there. There are PowerPoint presentations, of course, but also God knows what else. Videos? Sure. Executables (for some reason)? Of course. I need to literally dive into each of these folders, drill all the way down, see what’s there, and then remove what’s not necessary. And when that little project is done, I will have a clean version of this history, one that takes up less space.

I’ll get back to that in a moment. But first, remember that I have two organizational systems. The one I just described runs through 2011. By that point, the sheer weight of this “organized” but ridiculous system was clearly not scaling well. It was hard to find things, and I found that online search had improved to the point where it was easier to go to OneDrive.com and find things that way. And so I ditched the topic-based folder structure and moved over that year to the system I now use. Which is all date-based. I have a folder for each year (“2012,” “2023,” whatever), and those folders now contain month-based folders (by number, so 01 through 12). And everything I write in any given month goes in the appropriate folder.

I have adjusted this system once more to account for the fact that there are now so many date-based folders (literally 2012 through 2023). And while the details there don’t matter too much, I now have top-level “Work” and “Work archive” folders directly under “Documents” in OneDrive. Work has the recent stuff (folders for this month plus a few more older and newer), and Work archive is literally the archive, with all my old year-based folders. It’s clean, and it works for me, and it’s easy to just sync the bits I need to the PCs I use. And online search is my friend for the archival stuff.

To clean up my Penton folder (mostly my SuperSite folder), I decided to do what I did with my previous loose photo and scan pass: download it to a computer so that it is available offline and then go through it. When that’s done, I will copy it up to OneDrive to a new location (Work archive, under “Old”) and will, for the first time, copy it somewhere else too, to Google Drive (and perhaps to my Microsoft 365 Business Basic account, which also has 1 TB of storage, all unused). That way, this important archive will be duplicated in two cloud services. I will keep it on the NAS, too, of course.

And so I downloaded “Penton” to a PC.

This should be interesting. I’m curious about what I can delete, of course, but I will undoubtedly uncover some interesting things I’ve not looked at in quite a while. I assume I’ll get at least a few “Throwback Thursday”-type posts out of this. Maybe some additional material for Windows Everywhere. Who knows?

I’ll check back in when this process is complete, and then hopefully move on to more of this horrible but necessary work. But you may be wondering what this has to do with you. Other than a few of you being remotely interested in the archives I have or perhaps in my insane organizational schemes, what can you learn from all this?

A few things, I think.

First of all, different things are important to different people. I feel very strongly that my photos should be replicated in at least two cloud services, and I happen to use Google Photos and OneDrive, plus the NAS. But others may feel this strongly about important personal or work documents. I’m adjusting how I store my work document archive—to include at least Google Drive—but you should have some strategy for that stuff. OneDrive, for example, offers a Personal Vault for encrypted storage of personal data. And some will care about digital media collections, be they music, videos, or whatever else.

Second, I think it’s interesting to see how different people do things. Some may feel the need to be overly organized as I am, some will see this as a vindication for their own storage schemes. I will say that improvements in cloud storage have made my own scheme less important. It’s easy to find things online now. That wasn’t always true. (Indeed, I used to travel with backup CDs and then DVDs, not just to reinstall Windows and Office if needed, but to get at my documents too, in the case of a disaster.)

Third, it’s important to occasionally revisit what you’re doing—in this case from a backup/storage perspective—so you can make sure things are working as expected and that whatever system you’re using is as efficient as possible. Things change over time, and reevaluating from time to time can lead to positive changes. You can use this as a nudge to think about what you’re doing, and if you’re good, you’re good. But maybe you’re not.

Speaking of which, I was asked recently on Twitter whether Windows had anything like Time Machine, Apple’s macOS-based backup solution. It does not, aside from third-party software, I guess, but I feel that this kind of thing is old-fashioned and not necessary for most people today. (Related, it’s notable that there’s no Time Machine for Apple’s more modern devices.) I will write this up more formally, but thanks to cloud storage, more modern ways of restoring a PC to its factory-clean condition, and solutions like winget (the Windows Package Manager), one can reset a PC and be up and running with a truly clean OS image, the apps they need, and the data they need on that device very quickly. Conversely, one problem with traditional backup/restore is that you restore everything, including the cruft: you’re only as good as the restore image. Others are the timeliness and availability of that image. (In the meantime, Don’t Be a Statistic (Premium) speaks to the data sync part of that story.)

More on that soon too.