Mydigitallife |best| May 2026

I’ve been digitizing my existence since 2009—back when “cloud” just meant rain, and backing up meant burning a CD-R. I’ve kept every USB drive, every forgotten blog draft, every cringey forum post under a username I thought was clever. And last night, I finally sat down to sort through it.

I have six different to-do list apps from 2014–2018, each with tasks like “learn French” and “start podcast.” Spoiler: I did neither. But seeing those lists didn’t make me feel guilty. It made me realize how much my definition of “success” has changed. Digital clutter isn’t always procrastination—sometimes it’s just a record of our evolving ambitions. mydigitallife

So here’s my long-winded point:

If you’ve got a digital graveyard of your own, I’d love to hear about it. What’s the weirdest thing you’ve found in your own archive? And more importantly—are you keeping it, or finally letting it go? I’ve been digitizing my existence since 2009—back when

My “Photos” folder has subfolders like “New Folder (2),” “Misc,” and “to sort_ugh.” Inside those? Birthday parties, pet funerals, blurry concert photos, and one accidental screenshot of my own lock screen. I spent two hours just renaming things. The lesson? Name your files like a future archaeologist will be digging them up. I have six different to-do list apps from

Over the next month, I’m going to properly catalog my DigitalLife. Not for productivity. Not for social media. Just for me. I’ll back it up in three places, encrypt the sensitive stuff, and finally rename “New Folder (2)” to something like “Spring 2014 – Almost Happy.”