Flu changes from year to year. You also don't get everlasting immunity to the strains you do get. It can be just as bad the second time if you are far enough removed from your initial infection.
That’s not exactly accurate.
Unless you are immunocompromised, elderly or very young a person is not going to catch the exact same flu strain multiple times. For example, the most common strain right now is A(H1N1)pdm09. If you catch that, healthy people wont catch that same strain again.
However, there are a bunch of other H1N1 strains that are genetically different enough from this strain that you could catch. Maybe it’s lessened by having been infected before or maybe it looks so different you get really sick. It depends. But normal, healthy people won’t keep catching the exact same strain over and over.