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I'll be honest, I've been riding for 28 years, and the only time I'm ever wholly comfortable in canter is if there are jumps in the equation and I can't overthink it. If I'm focused on my next fence and keeping my horse balanced and ready for it, I don't think about the canter itself, I don't micromanage my poor saint of a horse into oblivion, I can let her roll along without jamming us both up, and it's smooth and comfortable.

On the flat, I focus too hard on is she round enough, is she flexed the right way, is she forward enough/too forward, why are my circles egg shaped (spoiler: it's my fault, my horse is very educated and has no difficulty with basic schooling figures), why is she cantering haunches-in I'm asking for shoulder fore (spoiler: I'm always asking for haunches-in), what is rhythm, why is she all jammed up (spoiler: I'm jamming her up), why can't I ride????? It's a whole thing and it frustrates us both to no end.

From a coaching perspective when I'm teaching somebody to canter I usually put them on a horse that only has one canter speed and let them roll along and get a feel for it. It's easier to find your rhythm if you aren't affecting the horse's stride at all. I really like the round pen for this because the rider doesn't have to think about steering or running into anything, they can just focus on themself. Sometimes it's easier in a half seat so you can get a feel for the movement without bouncing around.
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