It is very difficult when the market for art in general, or
your art starts tanking and you're faced with having to ask less for your work. It's not exactly "fair" to the collectors you've sold to in the past that have paid top dollar and considered it an investment in you. It's bad PR. It is a strike to the ego. It means you are worth less, your work is less meaningful, your reputation isn't as important--the whole nine. It sucks all around.
Personally, I've refused to cut prices based on the above depressing downers. In the 2008 economic crisis, I held my prices and just froze them where they were. I didn't raise them for years, but also didn't "lower" them. I did "discounts," which has a different social appearance, I guess you could say. The retail price tag stayed the same, but the gallery, or I, would give courtesy discounts of 20%-25% and if necessary, private sales were done for even less, depending on the collector, or how many pieces were being purchased, etc.
The whole point is to hike up the price with the economy (one would think), but in the art world, it's its own animal of course. The more important collections you get into, or the more you show in museums or get prestigious awards, the more you can hike the price up because it's all about perception and the reputation of the artist. It's all about PR and how well the gallery promotes your name and your work. And some galleries/sellers do this better than others.
This might seem to be the case only in the art world, and in a way it's true, but really, it's not that much different than many other "products" in the economy. Cupcakes, donuts, cars, pet rocks, houses, toilets, you name it, if someone markets something to be more special than something else that's essentially the same thing, it can sell for a lot more money and people think they need it--and will pay the price, despite quality. It's the "name brand" in clothing, or whatever else that people will pay for. It's marketing and perception. I guess, because I know this, it's why I try to hold on and just wait until the right buyer comes along and never fold on selling for so much less in desperate times. It might be a stupid thing to do, but that's what I've been doing for decades. Does it pay off? Probably not.
I have a tier system for pricing the art, depending on the materials and size, but I factor in how it compares to my peers who have similar sales histories and resumes and knowing what people will pay. I can't go too high, but I can't go too low. I can't increase too much or I'll screw myself in future sales because of the past. It's quite the balancing act. I raise the price very slowly over many years depending on my accomplishments and past sales. I have to factor in all these things and can't do a square-inch or hourly wage system anymore, but at least it is consistent with size and materials.
Whew, that was long.