Hello to my future self and to the approximately six people who might see this at some point!
It's cyclical and endless: thinking about how to align and weave the threads of vocation and of making a living. Or actually, alignment seems too neat, most of the time. It's more about ensuring that the threads don't get in each other's way too much, like all the cords in a server rack.
Around the 1 hour 45 minute mark of this excellent discussion, Jim O'Rourke and Samuel Andreyev discuss some of the different routes to trying to make a living while doing what one loves.
The prickly, pugnacious Chris Ott, not being totally wrong here, in an interview from some years back. I would love for smart people, including many friends and acquaintances, to be able to live lives as writers like the halcyon days of good magazines and publishing houses and so on. But I suspect that it will only help people to detach from that particular dream-path and keep thinking about the other paths. (Signed, someone who's already been down such a road, himself.)