I literally started by buying a bunch of cheap Waltham movements on eBay and tearing them apart. From there my progression was read a few books, watch some videos, buy some tools, join the NAWCC and go to some local meets, and meet local folks to teach me directly. Once you make some helpful friends who are a lot more knowledgeable and experienced than you are and are eager to teach, you're off and running.
I actually discovered pretty early on that my interest was more in clocks than watches, but the early explorations in the watch realm were almost entirely applicable to clock repair as well. I have since repaired at least a hundred clocks and pocket watches. Next month I'm going down to the NAWCC school of horology in Columbia, PA to take my third workshop there, this one on the repair of wooden works clocks. The school was closed for a number of years, but has fired back up in the past few and I know they're actively working on getting more watch repair workshops going. Last time I was there they were just putting together a killer watch lab with some very expensive benches and equipment.
I actually discovered pretty early on that my interest was more in clocks than watches, but the early explorations in the watch realm were almost entirely applicable to clock repair as well. I have since repaired at least a hundred clocks and pocket watches. Next month I'm going down to the NAWCC school of horology in Columbia, PA to take my third workshop there, this one on the repair of wooden works clocks. The school was closed for a number of years, but has fired back up in the past few and I know they're actively working on getting more watch repair workshops going. Last time I was there they were just putting together a killer watch lab with some very expensive benches and equipment.