What happens when a '90s star gives up on his music career?

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It has been particularly frustrating with one of my artists lately. His band hit it big in the '90s, and he hasn't been able to match that success since. He's kind of at a crossroads in his life, but at the same time, he doesn't like to adapt to the changing industry. We'll have meetings and split to-do lists, and he never finishes his part of the list. To top it off, he's broke and hasn't had the money to pay me for the work I've put in for the last three months. I don't think he's lazy; he just has so many projects going on, and he doesn't like doing detail work (stuff I can't do)--and he has no money-management skills.

I know that managing an artist is like babysitting, but I also work with other musicians that work very hard, and I don't run into this with them. My question is, how do I motivate him? Should I cut my losses and move on?

-Adventures in Babysitting

Dearest Babysitter, Every artist should be so lucky to have a thoughtful, genuinely helpful manager on their side. That said, when I look at the big picture of the issue here, I see two things. One, this guy is very likely unmotivated because he is not seeing any results (it doesn't help that he's not lifting a finger), and as you said, he's flummoxed by the new rules of music making. It's harder work and less money than in 1995. Diminishing returns are incredibly dispiriting, especially if in the not-too-distant past he was skating on a hit. Reclaiming a career probably seems Sisaphysian. Who wants to get down in the nitty-gritty of band management when it seems futile?

Now, normally, I am not one to suffer babymen who expect everyone else to do the heavy lifting so they can live their dreams of being an artist, but what may be happening here is he knows his ride has come to an end. So we must be a little sympathetic, because this is a really hard thing to come up against. He's perhaps paralyzed by the thought of his music-making career being over and what that means. He may not have other skills or interests. He's obviously 20 years deep into investing time and resources into making something happen. And now he's 38-50 and wondering what is the thing that he will organize his life around now and if he just wasted two decades on a pipe dream. That's a harsh toke.

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Jessica Hopper
Contact: Jessica Hopper