This is going to maybe sound dumb, but hear me out: I've found a good hack to get around the montage fallacy, which is: the montage playlist.

For whatever thing you're trying to improve, which would be a montage in your personal movie, make a playlist. Stick with it: it's fine to swap songs in or out, but don't overdo it, maintain the continuity.

Memory is episodic, and for my brain type at least, sound, specifically musical sound, really ties it together. Listening to music from bygone decades is the best tool I have to really put myself in my memories of those times.

The montage playlist works the same way: it compresses all the slow, repetitive, boring work that goes into improving yourself into a montage. It feels less like dozens to hundreds of hours, and more like the same hour but getting a bit better each time.