What Happens When a '90s Star Gives Up On His Music Career?
The other less charitable possibility is this: amid his success, he never had to learn to take care of his own affairs, to manage his career. And so it may not be laziness so much as he has always just been left to play the riffs and cash the checks and some 10-percenter has always been there to clean up his messes and shepherd him around. In which case, it seems unlikely you can teach him responsibility or throw some magic carrot before his horse cart that's going to change his mind about his role in his career.
Right now, he's treating you like a mommy, not even a babysitter (babysitters get paid). And you are letting him. Three months is long enough where for his sake and yours you need to put your foot down and say he's got pay you everything he owes you before you make another call on his behalf. Letting him skate beyond three months will create resentment, and if he stiffs you it'll be really ugly. You work for free for six months then he sees he can skate with impunity and it's just a terrible precedent; it enables him to continue to be bad with money and not take responsibility. He will count on you working for free by that point. He's an adult--respect him enough to allow him to reap the consequences of his actions.
This artist of yours sounds like he has bigger personal issues to work out, and that they are likely spilling out into his professional life. If you are going to work for free, do it for someone young and up-and-coming, some buzz band you can build with. Or a seasoned act who knows the ropes and can make connections and introductions you need to build your career--a situation that benefits you, not sucks you dry. Let this client go--he has to find his own way--and you don't want to throw months or years into trying to "solve" his problems.
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