The year that I got my first tablet was 2010, so that first drawing at the top left from August 2010 is actually one of the first pieces I ever drew on a drawing tablet.
In 2010 and 2011 like many people, the main website I went on was DeviantArt. I saw somebody that I watched do a redraw, and I wanted to join in. So, I ended up doing the second piece from 2011. At that point I had switched art programs, and had learned how to use a tablet more, so I felt very confident.
I thought of doing another a year later, but for whatever reason I didn't end up finishing it... So the real next time that I revisited this concept was two years later. At that point I really felt cool about it, and that was when I noticed that it was a real confidence booster doing this thing.
I've always had bad self-esteem about my art (especially as a teen), comparing myself to other people and all that. However when you're somebody who has bad self-esteem, and you compare yourself currently to your self in the past, you're certainly going to like what you currently made better than what your past made.
So that was when this tradition solidified.
I enjoy how it not only shows "improvement", but how it also showcases stylization changes / artistic decisions. I remember once sending it to a "friend", who said to me "Oh I don't think that 2014 is a very good representation of your art style, you're really going for something different there!"
But that's the whole point!
One year I might be trying to go for an ultra realistic style where everything is rendered, the next year I might be going for something very chibi, and another year still I might be using brown lines and making things very pastel.
I find it funny that the only years I've missed (so far) have been anagram years, being 2012 and 2021. As I said 2012 was something that I actually tried to do, but it didn't end up finishing it. And in 2021, I had kind of a rough year, so it just slipped out of my hands.
I'll be curious as always what this will look like in the future!