Why do so many legacy brands implode when trying to attract new customers?

There is a type of business story that has become nearly cliché: A legacy brand is facing stagnating growth. Loyal customers are aging out, and new customers aren’t taking their place. So the brand reinvents itself to pull in a younger segment of the market, often by borrowing ideas from cooler competitors to seem more “on-trend.”

But instead of younger and cooler, the rebrand comes off as insincere, stilted, or cringey. Worse, the brand’s older, core customers, who liked the brand as it was, are irritated by the changes.