I'm still pretty new, not only to the game but to the whole showing thing. I have my barn full of geldings and all I've been doing is training and tracking. So if anyone has any tips at all, for showing, breeding, anything in general, please let me know!

This means that your horse's training level is too high for their current rider. It is a disadvantage when showing. You need to assign a higher level rider.

Awesome, thank you!