I agree about setting small goals. I try to give my trainer a small list of goals every 6 months so she knows which direction to go with me. Back in May I sent her the following goals:
-- Able to WTC solidly. (Getting there)
-- Better transitions. (YES! This I've accomplished.)
-- Do a local flat show in Aug-Sept. (Now aiming for Feb-March)
-- Be able to do a short 18" course in lessons by end of December. (See Goal No. 1. Although it may still happen, if only at a trot.)
BUT -- there's been a lot going on with me at work, summer camps at the barn meant no lessons for about a month (I did hacks instead), my trainer moved barns, all the schoolies I were riding were left at the old barn, and for the past month I've been learning to ride a new horse. And I love him to pieces, but he's a bit quicker than the old WP QH mare I was riding before.
Then again, I don't really mind that I'm not quite where I want to be. I decided early on to be fluid with riding, knowing that I'm older and heavier and def. Out of shape. And because I have a 50-60 hour a week job, unlike when I was riding in college. I do push myself, don't get me wrong, but I don't want to put so much pressure on myself that it stops being fun.