Dylan? Read his book. It's all there, the honest truth for once.
And this idea of putting the music first, the good life etc, making enough to get by, is okay till late middle age hits, and old age looms. Where's the security? Where's the pension? If the voice goes or arthritis hits the hands, or the car crash maims you, it's goodbye, and if you ain't got it in the bank you're in deep trouble. If you're a pro in any job you work for the money first or you're a fool. It doesn't mean you "sell out", whatever that means, but it does mean that you treat it as a job just like any other worker who's trying to avoid the workhouse.
Or, as Dylan writes it, " I could see the future-an old actor fumbling in garbage cans outside the theatre of past triumphs."
It's a great book! But it's not a romance.