Your questions are perennial ones for anyone making a living in any field, I think, not just art.
I make a living with my portraits. I love what I do AND it is also a job, with regular -- and sometimes very long -- hours, tight deadlines, clients with very high expectations that need to be satisfied, plenty of bills to pay, etc.
I am running a small business here, as an artist, and anyone who wants to make a living doing this needs to understand that. A good portion of my time is spent doing administrative stuff, or repetitive stuff.
That is all balanced, though, by the wonderful pleasure that comes from creating something new, a painting that never existed before, and hopefully a beautiful one. The other day one of my portraits was delivered on the other side of the country and I heard later that the client was "jumping up and down with joy" when she saw for the first time. People often say and write all kinds of nice things about my work. That recognition doesn't come with a lot of other jobs.
And, finally, when it comes right down to it, many of my happiest hours are the ones I spend completely alone, in silence, playing with all my wonderful colors in the studio. That makes all the paperwork and deadlines well worthwhile.
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