20-Year Prospect
Are you feeling lucky? If you're blessed with a streak of good fortune, the prospects of staying employed as a jockey for many years is very good. However, if you're like most of us—good-hearted but generally pretty average in the luck department—a career as a jockey may not have the best longevity. Most jockeys don't continue riding past their fortieth birthday, so your career may actually only last about twenty years anyway.
Here's the good news: you'll know a lot about the horseracing business in general. As a jockey, you'll become pretty well-versed in the horse biz, so when you retire from riding, a whole host of equestrian options await you. Many jockeys end up training future jockeys or future race horses, but some—especially if they've amassed a nice nest egg with their winnings—become full-on owners of their own race horses.
There's also the question of whether horse racing will still be a thing in two decades. This may be a popular industry today, but as social values continue to change, and more scrutiny is placed on the horse-racing circuit, the sport looks like it might be in trouble.
Wherever you stand on the issue (if you end up being a jockey we imagine you're a supporter), remember that laws can always change. Be mindful of that if you decide this is the career for you.