I do some small design work for a favorite establishment of mine. I've done their website and a handful of band flyers. Recently I was asked to do a shirt design. The owner is a solid guy who for some reason doesn't do contracts, but always pays. So I spent 10 hours yesterday on no sleep and finished a design that he absolutely loved. Because that place has done a huge number for my social life and he's helped me out in a pinch with a few bucks sometimes, I discount him.
So I come in today and quote him at $100.
"$100, really?!". I informed him how much time I had spent on it with no sleep. He replied "remember I asked you to not put too much work into it". I said I do remember, but this is how long it took me. It was not a real ornate, complicated design, but it works quite well. I dropped the price to $75, where he replied sure, but that it'd be the last time he would hire me, as his previous shirt design guy (more an artist than a designer - and a good one at that, also a friend of mine I got to know there) did them for free. I said well, I value my work. And I really enjoy doing work for this place. As dissapointed as I was that the value wasn't seen in what I had done, I did something likely worse: dropped it to $50 and that he'd still hire me for future designs, at least flyers.
Agreed.
Now, had I quoted him upfront, this whole scenario would not have happened. There is a part of my brain that says "well I need the money, I don't run this as a fulltime business yet". I started school this year, but I have over 10 years of experience behind me. But once I got home I found myself on a fence as to whether I should take more money and be done with future work, or take the $50 and have some extra $ which usually goes back into the place anyway, as I'm a regular customer. A lot of these pieces I'm happy to have in my portfolio.

