Digital Decluttering: Resolutions (Premium)

Dumped unceremoniously into 2024, this feels like a good time to look back at the digital decluttering work I took on last year, provide a progress update, and then look ahead to what I hope to accomplish in the new year.

I originally expected my 2023 digital decluttering efforts to unfold similarly to previous years where a burst of activity and progress is inevitably undermined by distractions and other work and then a long period of inactivity. This is understandable and maybe even normal, as decluttering—digital or otherwise—is difficult and tedious. And it's all too easy to fall into what I now know is called doom piling, where you organize clutter rather than remove it from your life. I've been doing that my whole life.

But 2023 was different from past decluttering efforts. We moved from a very large house with infinite space to a very small apartment with limited space, forcing the issue on physical clutter. And in being confronted by what remained of the physical items I wanted to scan and discard—paper photos and documents, kids' drawings, newspaper clippings, and other similar items—it occurred to me that it was also time to organize and clean up the digital end of this process. This meant my documents archive, which dates back 30 years, and my photo collection—which spans my life and more, and I soon learned was multiple collections, none of which was a superset of the others—and other digitally stored content.

Without getting into the weeds, my document archive consolidation and organization and what I thought was my final round of paper scanning/digitization and organization both went very well. In less than a month, I had fully consolidated my document archive and replicated it in several online services and on a NAS. And as I wound down the scanning in a crazy long weekend of work—again, so I thought—this success inspired me to look at other digital decluttering projects, like cleaning up and organizing my legacy music collection and re-digitizing some home videos (including at least one that had never before been digitized).

And then I crashed. Hard. Despite not being done with my digitization work, especially on the organizational end, I decided it was time to take something I'd tried to do many times but failed at repeatedly and consolidate and organize my online accounts by separating my work and personal activities. But this went just as badly as it always had, and so I gave up on this task so I could focus, again, on a single task, in this case the photo collections and all the related unfinished scan organizational work.

Over the next two months, I worked with various offline versions of my photo collections and a growing set of tools to figure out the best and most automated process I could use to tame this beast. And then two milestones in November got me back on track: Google screwed over Workspace customers like me who used its storage upgrade subscription by canceling that offering, and...