In medieval England, horses used to be vastly expensive, something only the richest people could afford, especially just for riding (instead of plowing, cartage, etc.)

Hardly anyone could afford a horse, and beggars certainly could not. Wishing for a horse meant wishing for something vastly far out of the reach of most people, and a completely unrealistic fantasy for beggars. But if wishing (for a horse) worked, and actually GOT you a horse, then even beggars would ride (horses).

As a saying, it just means that wishes don't come true.

It's not really about working for and earning what you want; it's just about wishes being unreliable.

For instance, you can wish for good weather on the day of your outdoor wedding, but it might not happen, and there's no way you can work for or earn good weather. So your wedding organizer might say, "Well, if wishes were horses, beggars would ride," and then go out and reserve some tents, because you can't count on a wish coming true.

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