My response was a bit harsh, but I say these things from experience: I was just like the original poster and for many years I firmly believed in my skills, time and materials being worth x amount of dollars. I priced my art as such and as the work mounted and wasn’t being sold there was 4 issues emerging: little exposure to the right people, sub-par AND inconsistent art, prices too high, and little to no putting myself out there, ie, sticking my neck out and getting ppl to know me. I became bitter and blamed everything, everyone, calling out those ‘idiots ruining it with their cheap art!’. I made up reasons why others were selling and i wasn’t. “those silly buyers have no taste, that’s just decor art on artfinder”
So then 10 years of that, wandering around aimlessly without focus, full of self doubt, chucking art in the garbage because i dont trust if it’s good or bad, is it me or is it others not getting it? (was me). Changing styles, changing mediums, spiraling down, giving up for months at a time, quitting painting for a year, starting websites, social media accounts, then trashing them, restarting them, re-trashing them in a desperate vicious cycle, wondering if I am really cut out to be an artist??
1 pricey sale every 6 months was demoralizing, but even worse, a bunch of ‘PROPERLY’ priced art that never sold was like acid eating away my insides… and then looking at it and wondering ‘is it as good as i thought? i must suck!’ Or worse, i would go painting and start to hate doing it, feeling dread, feeling bored, feeling anxious or restless, wanting to run. I spent a number of years making large 1/2 done paintings which ended up in the dumpster, tossing thousands of dollars in paint and canvas.
I used to play mind games while painting to try to relieve the anxiety of failure, of knowing on some level things were going so wrong at all levels of my art career. I was doing things i wasn’t meant to, and i was self destructing in slow motion. This made the painting experience very negative. I had lost my way somehow.
As i spiraled downward I started to think ’ how far gone am I? What’s happened to me? When i first started painting in 2008 i was so full of happiness and excitement at the paint and just making a still life, showing it to wetcanvas or wherever and ppl liking it. I sold on DPW and was happy when someone bought it right away. I would get invited to an art show and make big paintings, not caring about the implications of the motifs or my ‘brand’ or ‘art story’ , selling them, and networking naturally. Now i just hate everything. My confidence is gone, i won’t make large paintings anymore, as a matter of fact they have consistently shrunk in proportion to my confidence(and money). Now they are 6x6, shall i go smaller? Oh, and why the heck am i making abstract art now?? Come to think of it, why am i wanting to build a printing press? Do i even like painting anymore?" I became convinced the answer was NO, so that began the nosedive, changing styles, mediums, trying this artist’s method, or that artist’s style, wondering the whole time what was happening to my mental stability, and why did i hate painting so much?? Why the hell couldn’t i sell anything and get the career rolling? I was submitting inconsistent pieces to unsuitable galleries all over Canada and getting no response, causing abandonment of my current art direction, which strengthened the downward spiral. Then i would rebuild up my courage, try something else, fail, blame the galleries, then abandon that direction too. Continue downward spiral.
I thought, perhaps i need to listen to more art marketing podcasts! So that’s what i did. But then the compare and despair set in: I found the successful ones (in my mind). How did these guys make those dollars? What’s their secret? Oh, and i’ll be sure to cut them down in my mind so i don’t feel so bad. Carol has the advantage of the DPW site , so that’s gotta be easy for her… let’s see, 1000 artists x $12/month…if only i started something like that. Do i know any programmers? Dammit! ok, What’s Roos doing? Oh, but i dont’ have money for those courses though. I’ll try the free stuff maybe. But I don’t want to build another website, in fact if i ever look at wordpress again my head will explode. hmm, What about Abbey? Why does she do those things over and over? Doesn’t she tire of that? And she has the advantage of oprah. Or Julian? lucky guy had real press…and that auction. Same thing with Duane, he started the whole bloody daily painting thing, that’s his advantage of course. Maybe i will obsess and see who i can cut down instead of painting. I’ll leave no artist unturned, that will justify my situation.
You think you have negativity? I was the king, nobody beat me. I was sure to have an artist friend who was also average and negative so i could gossip. I would love her rants. I also had an online artist DPW friend who couldn’t make it happen so i would enjoy her complaints too. DPW has gone downhill we were convinced! Time to abandon that too! That of course would do nothing to solve the real issues.
How much longer did this go on? 5 more years of hate and despair. To reset my head and get over all that negativity was really a miracle. The only thing that brought me back was my love of nature and the medium of paint itself being intriguing. I managed to keep that part unruined. I still have issues though, too much damage. It’s a slow recovery. Let me be your example of how not to do things.
I often fear that i can’t even give my art away, that my neighbors would say ‘no thanks’ (one of them has a big mouth and said one of my big landscapes didn’t look natural. I internalized that and it ate away at me for a long time and i grew resentful).
I have a huge amount of experience going down these roads the OP and commenters bring up. I used to think that one had to be a 100% full time painter and couldn’t divide their time. After 10 years of being poor and not being able to pay bills or buy canvas, i got a part time job and it changed a lot of how i view my relationship to art and money. Now i don’t worry about how i price because i can survive, and be happy basically giving it away for the next while, or forever if that’s all i amount to.
Sometimes it does bother me when i think, ‘i spent 4 sessions out in the rain in those damn woods with the bugs painting that canvas, i should sell it for more… hell, i deserve something for that’. But then i remember the kind of person i am , and that i need to get it away from me before i throw it out because I know that looking back at it after a month i’ll see it’s not so great, and it’ll be in danger of the dumpster, and then despair.
So here i am at the beginning again, but this time I’m just grateful that i enjoy painting with purpose, and so grateful that ANYONE likes my art at all, and is willing to pay even $1 for it, and I’ve sold plenty for $1. I spend $200 a month on art supplies and i sell about $20 a month worth of art via my DPW link to eBay, which takes 11% of my sales, so every sale is a huge loss. But i don’t mind because i need to know someone appreciates it and wants it, however cheap. I used to think i was immune to this ‘appreciation’ thing. But i’m not, i can’t really just paint and say ‘f-you world! i made it and so there!’
I also had to get over the idea that my art was precious to me, that i had ‘favorites’. This was so important. I used to think that i would be unhappy selling so cheap but I became ok with it. It was a matter of how i framed it.
I know that if my art is any good, it will catch on with enough exposure and ppl will ask for it. There are a few ppl on instagram i follow and they are very good. When they post they get questions like " is this for sale?" The answer is usually, ‘yes, but it’s sold already’. And these ppl don’t work on branding, they barely speak english, they have virtually no online presence. So this is the sort of signal that says ‘you can probably raise prices a bit’ 
This is my goal, and i know all this pricing talk is just really a reveal of the artist’s own issues with sales, and the best remedy is to let the market decide what the price should be.
It’s my 8th year of painting almost every day and only 2nd year I sell (still not that expensive like some people). But at the same time I’m so glad I didn’t sell my early art. Because it was terrible!! :))