Someone else I follow received an ask about their oldest personal files. No-one asked me but guess what I'm telling you anyway
I have a fair number of digital photos that were taken of me and my siblings in the 90s, saved directly to floppy in glorious Very Low Quality Jpeg. However, I believe the oldest files in my possession that I made myself are some mouse-drawn MS-Paints of my OCs from 2001, when I was 12-13 years old. They include my Everquest character (a half-elf rogue), a Zelda OC who was the daughter of Link and Ruto (yes, really), and a more original character named Lady Kasume which was a misapprehension about how to spell the Japanese name Kasumi. These bitmaps (ms paint didn't support export as png yet!) still have their exact original timestamps in google drive, somehow.
There's also a word document of fiction starring said Everquest half-elf rogue; the real timestamp fell off and I didn't think to write the date inside the file but I believe it's from early 2002. It was the first story of nontrivial length I ever finished. I refuse to read it, the cringe is off the charts.
"Lady Kasume" was heavily influenced by the goddess in Harvest Moon 64, my favorite game at the time. Her outfit also has obvious Final Fantasy white mage vibes. This character I made when I was 12 still persists in a form in the fiction I am writing when I am 35: her direct memetic descendent is Varodahn, who still wears very similar white mageish clothes and has a similar cold-and-sharp personality. She uh, switched from being an ¿Asian? character with anime green hair to being an African character with pretty standard curly dark African hair at some point. There was a phase in the middle where her skin was dark and her hair was white. The white hair got transferred to Ilmatar who is the original source of Varodahn's powers.
Glory in the Thunder: it's better than what I wrote when I was twelve.