That's the fastest "gradual" I've ever seen, haha. Awesome progress!
Thanks! There are still a lot of things I struggle to draw, but I’m a fast learner I guess. And like everybody else I’m my own worst critic. I think digital drawing tools really help decrease the difficulty level when it comes to the learning curve of teaching yourself how to draw.
So I don't have any from the absolute start but I do have some from pretty early on when I go my first tablet. I did stuff with a mouse on the school computers with photoshop before and a lot of work and traditional stuff so I have a pretty solid staring point. And I did a lot of drawing traditionally and then scanning the sketch, which really helps the transition.
This is from 2015 when I go my first tablet.
And my latest in a roughly similar style.
I've been drawing on paper for pretty much all of my life, but began doing digital art (sort of) nine years ago. With a mouse, because I had no way of getting a tablet at the time. I was mostly coloring my scanned drawings, but sometimes doodled with the mouse too. It was all seriously straining my wrist though 
(this is one such doodle from 2015)
I bought a tablet (to be specific, a cheap-ass second hand wacom lol) a year ago and it was surprisingly difficult for me to get used to it... it felt so completely different from drawing on paper. Ironically, my tablet sketches were worse than some of my old mouse drawings.
Took me around four months to even begin getting comfortable with it, and it took a whole year before I felt I could draw with a tablet the same as on paper. But I still prefer drawing on paper in some ways tbh (though I don't do it much recently). It was a long and arduous journey, but I'm glad I have not given up!
One of my first tablet drawings...
Part of my recent work (WIP)
This is one of the oldest digital drawings I have. It was before I had a tablet, so I'd draw in MS Paint with either a mouse or a laptop track pad.
I got a drawing tablet and paint tool sai back in 2014. The thing that I find most difficult about digital drawing is line art. I still heavily rely on a stabilizer. I don't know how artist can do without one.
This is where I'm at now. I use CSP now and I still have the same tablet, plus an iPad for drawing on the go. I think the iPad is a lil more slippery than a tablet, but it's quick to get used to and they also have screen protectors that mimic paper if it helps. I kinda prefer the iPad more since I can draw directly on the screen, but I still need a stabilizer.
I had just finished my first year of college and was still new to it. My roommate who was a classmate of mine was very talented and she taught me a lot about digital painting on Photoshop, since it's not something we covered in Photoshop class. I studied art, animation & web design.
I think this is the first digitally coloured piece. But, the drawing itself was done in my sketchbook. (Photoshop, 2004)
This is the first fully digital piece I did. It's one of the draft designs of the Winter castle for my current comic series.(Photoshop, 2005)
And this is my latest piece from this month. The cover for the newest chapter of my comic series.(Clip Studio Paint, 2020)
Oh... wayyyyyyyyy back around 2012 -2014
Not my first though, my first digital picture was... VERY badly drawn before getting used to it.
my current Art
Yeah theyre the same characters from my comic Devoured World; Neon & Regi (and V who i just ended up fusing his character into Regi) just designed better.
The initial idea for the story was Waay different back then
I really started digital art last year. So here's comparing a piece I did back in November and a comic piece that I've done fairly recently. The comic strip is supposed to come out the first Sunday of November, but I might as well share it so that you can see how much progress I've made in the past year.
Honestly, I'd really like to get a better handle on anime human anatomy. Chibi anatomy is really easy to get my mind around but human anatomy is a different story. 
I also want to learn more about effects in Clip Studio Paint too. That'd be a lot of fun!
I started drawing digitally two times. The first time was with one pretty trashy drawing tablet linked to my old laptop which needed an hour to process the most minimalistic things. I was 15 years old back than and it was a true pain in the ass.
This is one character sheet I did back than.
Now 6 years later tablets have evolved a lot, so I started again this march by drawing my first webcomic. Here are some of the first panels.
The comic is gonna be finished soon. Its so satisfying to see how the progress over the few months!
I got my first tablet in 2008
and here was a drawing from 2009 (thanks fb for keeping this lol)
And then over ten years later on the same tablet that I still use to this day
The biggest improvement digitally is just getting more confident with lines basically. Both pieces were done in Photoshop without any sort of line stabilizer. Also over the years I gained a stronger grasp of colors (from self-study) and anatomy (from college classes).
I started drawing digitally about 14 years ago? My guitar teacher lent me the tiniest wacom bamboo tablet that had a work area of like 3"x4" or something. I went and dug up some stuff I drew from ye olde internet annals.
Newest stuff (as of this year).
I always liked to draw, I have like, drawings since I was 2 years old (no joke - though they were obviously quite... abstract). By FAR studying reality even for like 0.0003% of the time is the fastest way to improve. Both the real world, and other artists' approaches to how they depict it. Yours truly is lazy so my improvement has been slow 
.
I was a traditional artist for the longest time, starting from a very young age. Around middle school I decided that I wanted to start taking art more "seriously" as a hobby (i.e. actually studying things like color and anatomy rather than just doing whatever all the time) and also started growing from primarily pencil and colored pencil into marker art.
At the end of high school/first year of college I got my first digital drawing tablet but... I admittedly didn't use it very often. Here was the first 2 works I ever did on it:
I used it here and there for the years afterwards, but I was busy with school and didn't do much drawing in general. I mostly kept to pencil drawings in sketch books and marker illustrations here and there.
After college I decided I wanted to try out comic making again (something I had done in middle and high school but not at all in college) and so I initially was going to try and do it in marker, but decided pretty quickly that altho my digital line art wasn't very good, it was still beneficial to do the coloring digitally for ease, consistency, & cost. That comic project flopped but I started my Tapas comic the following year, with the same work flow- trad inks, digital colors.
After a few months of doing that I decided I finally wanted to upgrade to a screen tablet in early 2019. I saw immediate improvements in most aspects of my digital art after that (the screen was part of it, but also upgrading from a tablet with 1000 levels of pressure to 8000 lol). I decided to finish the comic I was working on with the traditional lines but I started practicing more purely digital art on the side, including a short comic that was completed for an anthology last summer.
After ending that comic last December I took a short break from art. Upon starting up again I've been working in all digital finally this year. I would like to get back to doing some marker illustrations here and there tbh, but for comic work which is already super long and time consuming I've been loving the change to digital~
Here are some recent all digital pics:
. Also loving the space theme, been in a sci fi mood.