Many years ago, while out of work and undergoing radiation treatments for my cancer, I finally had enough free time on my hands to start a project I'd been wanting to undertake since the first flatbed scanner came into my life: digitizing the contents of my photo albums.
At the time, I really didn't have a system for organizing the photos, and over the years this has proven to be a huge problem. I had something like ten albums, so I simply named each photo with a sequential number based on which album was being scanned, followed by a short description that included the year. If there were multiple photos of a single event, I'd append an "a" or "b" to the end.
During the years that followed the initial completion of the project, that convention completely fell apart when I stopped printing photos and putting them into albums. Adding to the confusion was the fact that sometime around 2006, I'd purchased a new scanner that could digitize slides. The slide scans (of already scanned photos) were far and away better quality than the corresponding photos, but I made no attempt whatsoever to integrate them into the existing naming sequence, simply naming them scan1, scan2, etc.
After my dad passed, I got hold of his family photo albums and scanned all those photos into the mix. His albums were roughly organized by year, so in the interest of simply getting it done, I took advantage of that rough organization and threw the newly-scanned images into yearly folders. Unfortunately I made no attempt to properly name any of them, opting instead of a generic album name 001, 002, etc. At some point thereafter, I went back and moved all my photos into those yearly folders as well, since there was no reason to keep them separate.
The other day I was trying to locate a particular photo I knew existed in the collection, but after spending the better part of an hour coming up empty handed no matter what search parameters I put in, I knew the time had come that something had to be done about the hot mess that this photo collection had become.
I knew it was bad, but I didn't realize how bad it was. There were exact duplicates in the same folders with different names. There were duplicates with different names and years in different folders. There were the hundreds of scanxx photos, and I soon realized this was probably going to be a weeks-long (if not months-long) project getting this disaster organized.
Add to that I've been sitting on a dozen or so of my mom's family albums that are waiting to be scanned. My sister keeps asking if I've gotten around to doing it, and I keep putting her off, not wanting to wade into that without first organizing the mess I already had.
So the other day I created monthly folders in each yearly folder and started moving those items I had either previously named with a month, or knew with relative certainty happened at a particular time.
This time, my naming convention is year-month-numerical sequence-short description (where needed). In other words, 1989-06-0046-kevin ohm at sf pride.jpg. Fortunately Adobe Bridge has a batch rename function that allows me to do everything except the description automatically.
Even with that automation tool (and PhotoSweeper to weed out duplicates), at approximately 32,000 photos, this isn't going to happen overnight, but it is forcing me to rediscover a lot of photos I'd completely forgotten about.