Digital Decluttering: The Annual Checkup Went Poorly ⭐️

A few years back I spent a considerable amount of time decluttering my photo collection. OK, that’s a gross misrepresentation of the work, given the decades of photos I wanted to consolidate, how long it took, and how many times I failed before I finally figured out how to get it done. But whatever. What I was left with at the end was a clean and organized photo collection spanning 8 decades. And a small to-do item for every year of my life going forward.

Which I know sounds a bit odd. But this is specific to how I do things, including how I store and back up this collection. It’s not something I recommend to others per se, but because I move between iPhones and Android smartphones and use various cloud storage services, it’s even more complicated.

The good news? This annual to-do should be much, much easier and faster than the bulk consolidation I did a few years back. There are far fewer photos to deal with and just about all of them were taken with smartphones, so the metadata is good. I hope to automate this process as much as possible at some point, perhaps using some kind of an AI-based workflow. But for now, the process is anything but automated.

It’s 2026, do you know where your photos are?

I used several different smartphones in 2025, including the Apple iPhone 16 Pro Max, the Google Pixel 9 Pro XL, the Samsung Galaxy S25 Plus, the Pixel 10, Pixel 10 Pro, Pixel 10 Pro XL, Pixel 10 Pro Fold, and the iPhone 17 Pro Max. Lucky me.

I also switched to a set of Synology NASes as the “source of truth” for all my data, personal and professional, in 2025, though not all at once. I got the first NAS, a two-bay DiskStation DS224, that May and then a four-bay DiskStation DS423+ in August, and once I got them syncing with each other, I brought the DS244 to Mexico in September. So they’ve been doing their thing since then, so to speak. For the purposes of this discussion, there are two things to know:

• All the phones I use now back up photos to Synology using Synology Photos in addition to the other services noted below.
• Those backups land on the NASes in a different location than my now-organized photo collection. That is, where my phone backups go to home\Photos\MobileBackup with subfolders for each device, my photo collection is in photo\Photo collection.

Obviously, I want to have a backup of this Photo collection in multiple places with some geographic diversity. But I also use the automatic phone backup feature in Google Drive and OneDrive on all phones and iCloud/Apple Photos on the iPhones only. For now, Google Photos and OneDrive should both have completely, hopefully identical collections of all the photos taken across all the phones I’ve used. But really, Google Photos is the most complete because my wife and I are using the service’s Partner Sharing feature to sync her photos into that collection too. I suppose I could ask her to also use Synology Photos, but that’s a debate/discussion for another day.

This is a problem. Google Photos is the most complete. OneDrive is mostly complete, if you just consider my photos (and not my wife’s). And iCloud/Apple Photos only has the photos I took on my iPhones, not my other photos or my wife’s photos. And Synology Photos should have all my photos, but it’s not clear how up-to-date this is given the mid-year timing of these devices. This is all very irritating.

And there’s one more little nit: There are numerous screenshots I’ve saved that I can easily throw out, things I might have taken for work-related needs or whatever, but I also want to save some of them too. So part of this annual consolidation includes going through those manually.

Photos, photos everywhere

I used an unusual number of phones last year in part because Google was kind enough to loan me most of the Pixel 10 series phones for review–I purchased the Pixel 10 Pro Fold–but it’s also not that unusual. I always enter a year with at least one Pixel and one iPhone, the ones that were released the previous fall, and then I always end a year having traded in those phones for the new models that come out that year too. So there will always be at least four phones’s worth of photos to deal with.

Each time I trade in or otherwise move on from a phone–as I did with the Samsung Galaxy S24 Ultra sometime in 2024 when I gave it to my wife, who is still using it–I do two photo-related tasks. First, I make sure that Google Photos, OneDrive, and, on the iPhones, iCloud/Apple Photos are all up-to-date, sync-wise. And I also manually back up each phone’s photos/videos and screenshots manually. That is, I create a date-based folder–like 2025-09-21 Paul’s iPhone 16 Pro Max or whatever–on a PC desktop, connect the phone via USB, and manually copy all the photos there before factory resetting the phone for trade-in. Then, I copy that folder to an external USB hard drive and to the NAS. The idea is that I will use that folder as one source of data in my year-end consolidation (which should occur early in the next year).

When January rolls around, I start thinking about how I’m going to consolidate the different sources of photos I have from the past year. Again, this is phone backups in Google Photos, OneDrive, iCloud/Apple Photos, and Synology Photos, and the individual phone backups I created manually. The latter of which are augmented by slice-in-time manual phone-based photo/video and screenshot backups from the phones I’m currently still using, plus my wife’s phone. I went into this thinking that this beginning of year consolidation of the previous year’s photos would be relatively simple, and it will be, one day. But for now, it’s not because of all the phones I use, and this past year was, as noted, a bit more numerous than usual. So that’s fun.

In any event, I came to Mexico in January with a USB external hard drive that contained the manual phone backups and a partial Google Photos Takeout dump (which I had done and then deleted anything from before 2025; Google doesn’t let you do this by year or in any subset whatsoever, which is tedious). And I thought I would get through that fairly quickly. You know, once I figured out how I was going to consolidate it all.

But that did not happen. Not this year.

Photo consolidation

You might notice, for example, that it is May, not January. This is not me being lazy per se, but rather just a standard procrastination that occurs when I repeatedly start and then pause on a task like this that suddenly gets much more complex and time-consuming than I had expected. I had done whatever photo consolidation a year earlier, for 2024, but that, too, had taken longer than I had wanted and I never bothered to take notes about how I had done that work, which is stupid and also unlike me.

So for the 2025 consolidation happening in 2026, I had resolved to set this right. Which meant two things, figuring out a way to automate this as much as possible but also taking note of how I did this. You know, pay it forward to future Paul.

This has not gone well. I reviewed the articles I wrote for the Digital Decluttering series in 2023, of course, with Digital Decluttering: Tagging, Deduping, and Replicating the Photo Collection (Premium) being perhaps the most pertinent. I had also backed up all the utilities I mentioned throughout that series to OneDrive, Google Drive, and Synology Drive, though most of them were by 2026 a bit out-of-date and would need newer installers. But a good starting point.

In that previous linked article, I wrote about two utilities that I had used during my previous mammoth photo consolidation work, Bulk Rename Utility (BRU), which is complex but superior, and MediaSorter, which is simpler. BRU was superior for my needs because it better handled files with poor or missing metadata, among other things. But I figured I could get away with using the simpler MediaSorter now because these were all phone-based files with solid metadata.

So that’s what I did.

Long story short, this simply involves configuring MediaSorter to work with all the photo and video formats it supports and copying the files from a source (each backup, in turn) into a folder destination in which everything is organized using a YYYY/YYYY-MM-DD subfolder structure. MediaSorter has a nice duplicate detection/removal feature, but I didn’t really use it per se because I used a different destination folder on a laptop’s desktop for consolidating each backup using that structure with the idea that I would manually move the results into a main, consolidated folder as I went.

Why? Because of yet another thing that is unique to my situation: Because I take so many product photos for hardware reviews and other write-ups, I have all these photos of phones, laptops, and other devices that I don’t want in the final, consolidated photo collection. (To a lesser degree, this is true for work events where I may have dozens of photos of people talking on a stage or whatever. So I want to remove those as I go to.)

This is a key area in which I intended to automate this process. Surely, I could open a consolidated and organized (by YYYY/YYYY-MM-DD) folder and just use the search box in the corner to search for “phone” and “computer” and delete vast swathes of these unwanted photos in one fell swoop. Surely. But to slightly misquote an excellent Nate Bargatze joke, I’m not sure File Explorer knows what “one fell swoop” even means.

Sigh. I considered using a third-party tool to automate this. For example, the Everything app does a better job of searching a PC than Microsoft does. And who knows? Maybe someday I could make that work. But in the end, I decided to punt on this automation and just view each consolidated and organized folder on my desktop using Everything, scroll through the photos it displayed, and then delete all the product shots and other images I didn’t want.

This … “worked.” But it is not an ideal way to do this work.

One small issue is that I would see photos with incorrect rotations while I scanned through each folder in Everything. In File Explorer, you can multi-select image files and then right-click and choose “Rotate to the left” (which is usually the problem in my case because the iPhone is stupidly bad at this problem) or “Rotate to the right.” But in Everything, those options won’t appear if you select two or more photos. You have to do this one photo at a time.

Another small issue is all the screenshots and other image files saved to the phones. I thought this would go quickly, but it didn’t even though I did, as expected, delete most of them. The problem here is that I really need to look at each as the ones I want to save, often some interaction with kids or whatever, are things I really want to save and be sure of. I can’t just bulk delete these files.

The bigger issue is that I have so many photos of PCs, phones, and whatever else that I want to get rid of. So, depending on the source of the folder I was working on, this process could take a long time. For my Samsung Galaxy S25 Plus backup of roughly 1000 photos, this wasn’t too terrible in that I was able to manually delete the unwanted photos in about five minutes. But I also deleted over 300 files (out of roughly 1,000), which speaks to the problem. I take a lot of work-related product photos that I do not want to save forever. And this was a small data source. My Google Photos Takeout download of almost 35,000 photos took almost two hours to get through this way. Ugh.

Each time I cleaned a consolidated/organized folder like this, I moved its contents into a “CLEAN” folder that would eventually contain a truly consolidated/organized take on the full year. The idea here is that most if not all the photos I’m moving over will eventually be duplicates because many would have already been copied to this CLEAN folder thanks to all the redundancy of these backups. But here, especially, I had to be careful: If I allowed MediaSorter to rename the files as part of the organization (which is the default), then duplicate photos would have different filenames and not appear to be duplicates to File Explorer. Doy.

Still left to do is replicating this consolidated/organized year to Synology and all my cloud services.

But there’s more, really. I’m not happy with this. I didn’t do this work in a way that is manageable and while I can absolutely document what I did, I don’t want to repeat this next year. I would like this to go more quickly and require less manual work on my part. In fact, I’d like to do that right now. So I may go through this process with a subset of the data to see if there’s a better way. Just not right now: This was so tedious that I just want to stop thinking about it for a bit. Which explains the January to May gap, I guess. This work is terrible.

This is a job for AI, I think. I will look into that as soon as I recover: Soon, perhaps in June, I will do an AI focus month and this is on my to-do list for that.