Many people educated in music with lifelong skills and talent are boring...
often they split into four primary categories
unable or unwilling to work with the commercial industry -- some have lengthy careers but often those of this variety never achieve great and lasting commerical success. Many actively eschew it.
if they work in formal music or musical theatre, it's highly competitive and they have a much shorter shelf life... those industries are much more structured and has greater personal demands. They have very little control over their careers outside of side projects. Most burn out before they ever achieve "success" and the ones that do tend to veer towards coming off as sociopaths.
then you've got the historians, which are often performing educators and activists... but despite what commmercial successes they may have, their primary work is often of the non profit variety. . . and not the cause of the week type. More the dreary, dusty tomes, museum types. And much of the public desires mind-free entertainment. . . the emotive, aesthetics, sense stimulating, not the intellectual.
then you have the commercial. Most really only got famous as a school project. It was never their intention to become "famous," so they bail after the first album or two and use it as means to pay for their education or move more quickly into their 'professional' field, such as education or the technical side of the industry. Also, quite a few dancers in this category that never became known for dance. So, they fade out of public view.. or worse yet, become like the majority of commercial artists and abandon everything they know for the trends, often succumbing to excesses of celebrity. . . and crash and burn that way.
many classically and professionally trained.. lack imagination, innovation and often just the taste level to succeed. There's many great technical singers and musicians but you'd swear they're somewhere on the spectrum because they never connect with the material. They require conductors and directors, editors, a team of people to guide them through even the baby steps of a single song. (one example, I was surprised how quickly Patina Miller got a major role because if you had ever caught her university performances, they had to painstakingly explain the motivations behind virtually every song. She was way too serious and couldn't grasp humour at all.)
While we recognize the many problems of the untrained, self taught and autotune counterparts, often such performers break even or even sink lower... because they didn't leave any room for themselves to grow.