>Where has the time gone?
I feel you. I feel like I'm living the fable of the man who could pull on a string and fast-forward his life, except instead of pulling on a string I'm watching MLP.
>Tell me about your life when you first got on the ride and what got you on it
I was a stupid high school teenager who had just discovered masturbation and internet pornography. I saw some weird colourful gallery by syoee_b, clicked it out of morbid curiosity, and was left wondering who all the characters were. I actually hadn't heard of the show at all, and only after I started searching for it in the forums I used did I realize there was this weird new cartoon on the air, and that internet people thought it was neat.
I think season 1 was just ending when I watched the first two episodes (so, spring 2011 or something?). The surprisingly decent animation/jokes, plus the cute characters, plus the earnest fantasy setting really intrigued me; I also thought Nightmare Moon was cool, so I watched a couple more episodes and was mildly disappointed when the series became "just another slice of life cartoon," whereupon I stopped watching.
. . . For all of a week. I felt this niggling compulsion at the back of my head to watch the rest of it and see what everyone was talking about, so I saw the rest of season one and decided I'd keep up with the series. This was during the first ever drought, between S1 and S2, so I had plenty of time to fantasize about how the world worked and wonder what lurked beyond the mountains or across the sea.
I want to emphasize how much the setting was a factor. I grew up reading many fantasy novels of questionable quality, so the casual ways magic interacted with the characters' lives was really, really cool. There were simple things, like having an annual race to help shake the autumnal leaves off the trees and having literally manufactured weather overseen by the pegasi, or more complex things like the all the different races lurking in the borderlands: parasprites, diamond dogs, dragons, the sea serpent, etc. Fantasy cartoons aren't really popular these days, and many of them are victims of irony poisoning (such as Adventure Time) or downright bad production values. FiM was different, because it had a bunch of fantasy tropes and played them straight. That earnestness was something I always loved about the series, and it's part of the reason I grew jaded in later years after seeing many interesting plot points and characters undone or ignored in favour of cheap jokes.
>tell me where you're at now and where you're headed.
I'm trying to graduate a local college with a diploma that will enable me to find actual work, but I'm an only child so my parents' money and the money I made from previous odd jobs has helped smooth things over. Personally, I've taken up jogging to lose weight, which has been great for my health and mind. Gamergate helped me swallow a bunch of redpills, and I'm now trying to live according to golden age principles in an era of rot and degeneracy. Such is life.
I'm also thinking about converting to Christianity, but that's another story.
One of my closest internet friends, whom I met through pony fanfiction, is a bit distant due to some personal stuff that's been happening with him and him having found gainful employment and actually gotten off the ride. I was nearly in the same boat, except the gen 5 leaks renewed my interest in the series, so I'm watching a handful of episodes from S9 to see the series off and lament about what happened to it.
I'll probably watch the first few episodes of gen 5, but I think we all know it'll be awful. As far as I'm concerned, gen 4 had two good seasons before falling and promptly being zombified in the name of marketing. I don't think there's a single thing from later seasons that actually improved upon anything established in the first two years. That's good enough for me: instead of writing autistic fanfiction about characters I don't own, I can take the aspects of them that I liked and try to make my own characters for my own creative endeavours.
I think I'll always want to marry Princess Celestia, though.