Digital Decluttering: Photo Management (Premium)

Three weeks ago, I wrote about my latest attempt to scan in our old photos, distribute them to various online services, and then destroy the originals. Since then, there’s been a whirlwind of activity: Thanks to a reader suggestion, I moved to a high-speed photo scanner, and quickly blew through all of the 21 photo albums-worth of photos I still had remaining. Since that, I’ve started working through the boxes and boxes I have of loose photos, which include photos still in envelopes (which are well-labeled, somewhat labeled, or not labeled at all) plus a surprising number of literally loose photos that will require some work identifying.

There’s a bit more to it than that, as well: We have other documents and items that need to be scanned in some way too, like birth certificates, old passports, ticket stubs, greeting cards, kids’ drawings, and much more. But the basic idea is the same for all of this stuff: It needs to be digitized, organized, uploaded, and then managed in some way. This content also needs to be enjoyed, at least occasionally, too.

Hopefully, your own photo scanning efforts will be less troublesome than mine. I’m about halfway through what I’ll call the loose photos as I write this, and I’ve scanned in over 7,500 photos so far. In the course of doing this, I also discovered older scans from 2004, 2005, 2006, and 2017 that needs to be sorted and managed as well, and there are almost 3,000 scans in those collections. I figure I have another 2500-3000 scans to go, at least. So the total job here, if you will, should land somewhere between 12,000 and 15,000 scans.

This requires a clear understanding of the end game. And some serious organization.

My goals are simply stated. I intend to scan in everything—photos and whatever else; let’s just call them photos for simplicity’s sake—and then destroy/throw away virtually all of it. I will “tag” every single photo with at least a date, and that date will be as correct as is possible. I will then upload the photos to at least two online services, and copy them to my NAS.

The details of how I’m achieving this are, of course, a bit more complicated. So let’s step through this.

The scanning itself is simple enough, and the high-speed scanner, as its name implies, makes this process a lot more efficient. It’s not perfect: The scanner software will auto-create filenames and tags with the month and year of photos, but not the day, plus a subject/title. And you can optionally create a subfolder for each batch of photos, which I do.

Here’s how I organize the scans as they happen.

I use a separate folder for each event. I prefer to use a naming convention like date – event (for example “1988-03-07 Jon’s birthday”) so that the events are alphabetized, and thus ordered by date, with a year folder (1988). That’s not what the scanner software creates, not exactly. Instead, it will create a folder called “1988_March_Jon’s_birthday,” using the same example. And it will date each photo within that folder with a “Date taken” tag of 3/1/1988 and a time of 12:00 AM.

So, some editing is required.

If I know the correct date at the time of scanning, I’ll rename the folder then (to “1988-03-07 Jon’s birthday”) and bulk edit the Date taken tag for each photo it contains (CTRL + A, right-click, select “Properties,” navigate to the Details tab, select “Date taken,” and use the arrow keys to move between the month, day, and year fields.

If I don’t know the exact date—sometimes I just know the year, season, or even less about a photo—I won’t bother with this renaming yet. The idea, for now, is to pour through as many scans as possible, as quickly as possible, and then get the ones that can be uploaded ready for that.

From an organizational perspective during the scanning process, I maintain three main folders:

1. To sort. These are the photos and event folders for which I don’t have an exact date. They will be dealt with last, after all the scanning is complete. There’s a good reason for this. In many cases, the loose photos complement previously-scanned events, or fill in gaps. By having completed events scanned first, I can later fill in those gaps. So I put those one-offs and unknowns here.

2. Edit and upload. Photos and events for which I have the exact date—thanks to good descriptions written on photo envelopes or albums, in many cases—go here. These photos will be processed as described below and then uploaded to the online services I’m using. More on both of those items in a bit.

3. Uploaded. After photos are fully tagged and processed, they’re uploaded to two online services (and my NAS) and then moved here. These are the photos that are effectively “done,” and I’ll probably just delete them eventually. But I’m keeping them around now to track my progress.

(There’s actually a fourth folder, called Earlier scans, that has the scanned photos I previously made but never sorted. I will get to those at the end of this process.)

When photos or events have been correctly identified by date, I process them by rotating them as needed—vertically-oriented pictures come in at a 45-degree angle—and correcting any red-eye issues. I examine each photo to determine if there are any cropping or other issues as well.

When they are as correct as possible, I upload them to both Google Photos and OneDrive, and copy them to my NAS. The latter two use the same folder structure, which is why I use the folder naming structure I noted above. There is a Pictures folder in OneDrive (and a Pictures share on the NAS) with a Photo collection folder that contains year (2000, 2001, etc.) folders. So the photos and event folders are copied to the correct locations in each. With Google Photos, I simply bulk upload the whole lot: Google Photos doesn’t care about folders, and it uses the Date taken tag to ensure that the pictures are arranged in rough order. (I say rough because all of the photos have the same timestamp, so they sometimes appear “out of order” within a given day or event. Whatever. There are too many photos to change that by hand.

(I do recommend both Google Photos and OneDrive. But I should probably also consider using Amazon Prime Photos, since Prime members like me get free unlimited storage there as well. I wrote about this about a year and a half ago in Amazon’s Prime Advantage (Premium).)

Processed photos are then moved to the “3. Uploaded” folder.

As I go, I am throwing out the original paper photos and albums. And I back up the entire scanned folder structure to another PC and an external hard drive for redundancy purposes. After all, many of my originals are all in a single physical location otherwise, and I want to make sure that I don’t lose the only digital copy of paper photos I’ve destroyed. (What if there’s a fire, you may wonder. Well, that fire would destroy the paper copies too, anyway, and I’d have bigger issues to worry about.)

As I write this, I still have a bunch of loose photo scans to complete, but given my progress so far I feel that I will complete the actual scanning within a few weeks at most. This will let me turn to the less-well organized and loose photos in “2. Edit and upload” and finish them off. In cases were no actual date is found, I’ll just guesstimate, and my wife will help with the photos I can’t figure out. But eventually, those will be fully organized, tagged, processed, and uploaded. And then they’ll be moved into “3. Uploaded” as I go.

Some have asked me what the point is of doing this: How can we possibly enjoy these photos in any meaningful way?

Well, we weren’t enjoying the photos that have been sitting in boxes, in many cases for decades, anyway. This process has made me confront my own personal history, and my family’s history, and that’s been very interesting. There are painful moments from the past—like the time my one-year-old son almost died, in 1999—that I’ve buried those memories what I assume are obvious reasons, and having to see the photos of these events (in this case from his time in the hospital and then his later surgeries) and then actually organize them and save them, has been … well, therapeutic.

More generally, we have a Google-powered smart display that automatically displays pictures of our family members. As my wife and daughter have both commented on the sudden upswing in photos they’d never seen before, or had forgotten about, thanks to the scanning. Google Photos is also transforming these new uploads into stylized photos, movies, and more, and in the years ahead, I assume I’ll be shown “rediscover this day” notifications for these scanned events as well. Say what you will about Google, but this part of its far-reaching empire is pretty magical.

But as I wrote before, the most impressive thing about this whole process, at least to me, is that it’s now very clear that I will actually complete it. I knew the memories were there, and I always wanted to digitally convert them and rid our home of all the boxes. But I always believed I’d never really finish that, too. And now I know that I will finish it.

There will always be more to do. But for now, I’m just happy to be making progress on this.