The first thing that must be said is if you’re happy, the answer can be never. Over many years I’ve had riders who’ve stuck with me literally for decades—they’ve graduated from horse to horse and level to level. In many cases they’ve gone back to start the process all over with a young one, sometimes more than once. Through it all, I have tried to guide their choices, including encouraging them to experience other teachers, trainers, and clinicians to make their education as broad as possible.
Having said all that, sometimes there are reasons to move on. The Psych 101 term for it is relative deprivation. If you sense there’s something missing, if you see other riders are developing, and you feel that you aren’t, then you have to decide why.
From the teacher’s point of view, I have to remind you that being unable to be happy with your riding or being unable to achieve your goals may involve factors beyond your instructor’s control. Are the goals themselves reasonable? Are you able to devote enough time to your horse? Are you fit enough to hold up your end of the bargain? Is your horse appropriate for the task? A basic reality check is called for before you do anything radical.
All that said, there are times to go. Unless you are driven to be in the next Olympics or are of the Misery-Is-All-I-Deserve approach to life, the basic question is: “Are you going home satisfied?” Concrete achievements are one measure but certainly not the only one. Simply relating to your horse in a way that brings you comfort can be equally worthy. Knowing that your teacher is really interested in your well being is another. (But do be aware of the creed of some instructors: In this business sincerity is the most important thing, and if you can fake that . . . Well, you know the rest.)
So look around. Are you getting where you want to go (wherever that might be)? Are your peers leaving you behind when you don’t feel that should be happening? Are you being asked to progress way too fast? Or way too slow?
Again from the teacher’s perspective, we see examples of Dressage Whores—riders who jump from one trainer to the next to the next to the next, searching for that magic bullet—the secret formula—that will break them free and send them on to bright lights and success. Those are the absurd extreme. But if you’ve been honest with yourself, and if you think you can move on to an alternative that’s better than your current situation, amicably packing up and headin’ West can be just the right thing to do.