Assertiveness is, in my experience, a facet of self-confidence. So it may be that the common lack of assertiveness in riders is closely related to a lack of self-confidence. Improving your self-confidence is a conundrum. People who are urged to be more self-confident will ask, and rightly so, “How can I have the confidence to be more self-confident if I lack confidence in the first place? Isn’t this a catch-22?”

I think the answer is both “yes” and “no.” I like the saying, “Boldness comes from confidence; confidence comes from success.” So you have to begin by guaranteeing success. The way to guarantee success is to begin with tasks that are ridiculously easy and gradually build from there, backing up if things start to go wrong. It’s like desensitizing your horse to that scary ditch.

There are three things you try not to do when teaching a horse a new skill. Don’t hurt him. Don’t scare him. Don’t get him wildly excited. Similarly, if you are trying to build your self-confidence, don’t hurt yourself, and don’t scare yourself—too much. You have to scare yourself a little to give yourself something to build on, but only a little. Keep doing the slightly scary thing until you have had so much success that you know success is inevitable. Then make whatever it is that you are trying to do a little harder. And so on. (At some point, it will get too hard, no matter how talented you may be.)

You can be timid, or shy, or indecisive, or reticent. You can be burdened by any one of many afflictions that result from a lack of self-confidence, and you can improve every one of them if you can figure out a way to scare yourself just a little bit. Too big a scare, and you will find your self-confidence in pieces on the ground.

If you don’t like public speaking, don’t start by addressing the Republican National Convention! Instead, maybe you could start by addressing Cub Scout Pack Three, so that your listeners are nine years old. Ski down the bunny slope first, not the double black diamond.

Jane Savoie is an internationally accomplished dressage rider who has written motivational books and is in great demand as a speaker. One of her stories that I like best describes how, if you put fleas in a jar and screw a lid on it, the fleas will initially hit their tiny flea heads against the lid while attempting to jump out. Some sixth sense then tells them exactly how high the lid is, so that they keep jumping—but not quite high enough to hit the lid.

Now, when you take the lid off the jar, the fleas will keep jumping—and although they could easily do it, they won’t jump high enough to jump out. They have it in their tiny flea brains that the height of their jar is their limit. “So,” asks Jane, “aren’t we like those fleas? Don’t we all have limits that are only real because we believe them to be real, not because they are real in fact?”

I told that story to some Radnor Hunt Pony Clubbers I was teaching in a clinic one fall. When I returned the next year, a little boy came up to me and said, “Denny, I’m a lot better this year. I have a much bigger flea jar!”

You can build yourself a much bigger flea jar (see image above). At some point, it will be so high that you won’t be able to jump out of it—you are, after all, only mortal—but it might be very high, much higher than it is today.

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An excerpt from How Good Riders Get Good by Denny Emerson. Published by Trafalgar Square Books / HorseandRiderBooks.com. Order here.