And if you've done this, how did it go?
I'm thinking about it. I've made a certain amount of headway in my creative field (writing) by doing it as a hobby for years and years. It's very difficult to make money as a writer, I know, and I don't want to quit my current job just to do, e.g., copy-writing. I want to try to make a career out of the kind of writing I love.
My question is, as I can afford to do this financially (will obviously be poorer, but still fine), will I regret not trying? My current job is nice, comfortable and boring. It gives me time and headspace to write outside of work, which is great, but part of me feels like I'm not really putting my all into my writing because I have a comfortable day job. On the other hand, trying to make it a career might take all the joy out of it, and maybe right now I have a good balance.