The friends-and-family discount that became a year of my life
Painted a 120x150 for an old friend's anniversary two years back. She told me, tearfully, she couldn't afford my gallery price and I said of course, don't worry, we'll find something. Named €600, which was about a third of what that size goes for. She spread the word, quietly, and for a year after that I got three more people "from her circle" who all wanted the same deal. Each one I had to find a way to say no to without making her look bad. The painting itself was good, actually maybe the best of that stretch, and part of me still resents it. Not her. Me. I set the number and I treated my own time like it was worth nothing when a friend was on the other end of it.
I've started telling younger painters in the academy a simple rule I wish someone had given me: the discount should come out of your profit, not your hourly rate. Figure out your real number first, then decide how much of it you can afford to give away. If you can't afford to give it all away, you can't afford to give it at all. I know it sounds ungenerous. It's actually the only way I stayed generous at all.
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The number you set is the line you draw around yourself, and nobody else is going to draw it for you. I learned that the hard way too. You give a friend a break because it's a friend, and before you know it you're not an artist anymore, you're a discount department store that happens to smell like turpentine.
The resentment toward yourself is the honest part. That's the bit worth keeping. Not in a punishing way, but it's the only part of that year you actually controlled, and remembering it means next time the word 'of course' doesn't come out of your mouth quite so fast.
The painting being good though. That's the thing I'd hold. The work doesn't care what you charged for it. It's yours, all of it, forever.
"Line you draw around yourself", yeah, that's exactly it. I've said no to strangers about pricing a hundred times without blinking. The friend is the one that wrecks the line, because you think generosity is the point, and then suddenly it's a going rate.
The self-resentment bit, you're right that it's the honest part. But I'll tell you what's uncomfortable: I still don't fully know if the painting was best of that stretch because it was genuinely good or because it had all that weight in it. Some of my best work came out of situations I'd never repeat. That's a strange thing to sit with too.