When do you raise those prices???
The best idea is to raise them when you are JUST about busy enough for a rest.
In all things, it is a supply and demand situation. The best way to tell if your skill is increasing is to see how much the public is demanding you.
If you can keep up with your orders and you like the pace and income, you are just right. If you are a bit too busy, raise the pricing. One or two potential clients will not consider you but the rest will replace the income and when you get back to the same rate of production, your income will go way up.
It is not the BEST idea to arbitrarily keep raising prices without the equivalent demand.
It used to be hard for me to avoid the urge to keep discounting, but the client who sees what they want appreciates the simple and direct answer. I am much more comfortable with explaining my pricing is increased with added content... AND sticking with it!!
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