One of my early pricing successes happened because I simultaneously broke two of my favorite pricing rules: never volunteer discounts and large discounts work against you.
I offered a large discount, 66% to be precise before the client asked for any discount. It allowed me to get the project and sell the next one at 2x, and the one after that at 3x the initial price.

Why I think it worked:
- I was young, and my company was small, so I had the advantage of being underestimated
- The client was eager to show off in front of their boss, likely blinded by the opportunity to show the big initial discount as something he achieved
- I couldn’t stop them squeezing me anyway, so giving the discount before they brought it up gave nothing away that I wouldn’t lose anyway
- My suggestion of such a large discount prevented him from asking for more, as it would sound unreasonable
All of the above masked my goal: I gave them large discounts but under very clear conditions: you never worked with me and I don’t have any good references yet. What I omitted to point out was that these conditions would be removed with them buying the first project, allowing me to cut the discount for the 2nd and 3rd projects significantly.
Rules are great, but initiative > rules. initiative allows you to make the client “play your game” instead of allowing them to get you defensive about how much you charge.