How long did it take you guys to "get good"?

I try and play Risk for fun, it's become my ritual to play late in the afternoon almost every night. And while I enjoy the game, I suck. Miserably. I think I'm on a 30+ lose streak and only just breach into intermediate on my good days. Sometimes I make mistakes in games and I can laugh it off, but it really gets to me when I repeat them.

I think I've basically mastered (most) of the free maps on fixed and progressive, but when I try to escape my comfort zone with Capital Conquest, Fog of War, and the Advanced Maps I just make the stupidest plays and I feel like I ruin the game for everyone. I enjoy playing both casually and competitively, I guess I'm trying to figure out if I've reached my peak skill level or if I'm lacking a sort of natural talent/problem solving skills to get better at Risk.