1. Is there possible exposure in it for you?
I know, I hate that word too. But if the client has huge name recognition and an enormous following, I’d be willing to be (a little) more flexible on my pricing. However, be careful with how much you capitulate. Exposure doesn’t pay the bills.
BUT make sure that the exposure is written into your contract! If you are really giving them a discount, you have to make sure the client holds their end of the bargain. Make the discount contingent on them making a social media post about you, putting your name on all instances of the artwork, and/or allowing you to advertise on their website.
2. Will this project actually lead to more work?
I might be more willing to compromise with clients on price if the client will have a lot of recurring work. In the long run, you really save a lot of time (money) by working with the same client again and again.
The hard part is developing the psychic abilities to determine which jobs will actually develop into recurring work – because in reality, it is a rare occurrence, especially when working with a start-up business, who still has stars in their eyes and may not know the challenges ahead of them that will change their business plan.
NOTE: If the client asks for a lower price because they say they will have more work for you, don’t take their word for it. Instead, I offer them bulk pricing. For example, I’ll give them a break in cost if they pay the deposits for three projects up front (for example). This way, they are committing to you, and you are rewarding them for it.
While it’s not a written rule, I typically charge 10% less for bulk pricing.
3. Will this project look good in my portfolio?
If it’s something I really want to do, and I think it will turn out awesome, I will sometimes lower my price to meet the client’s budget. Especially if it fills a hole in my portfolio that I think will attract new clients.
But make sure you’re not doing this too often. If you take this project for a low price, and all it leads to is more low-price work, then you’re going to get stuck in a trap.
4. When is the deadline?
If they don’t want to pay your full price, they shouldn’t expect to be on the same schedule as the clients who are paying your full rate. I’ve taken projects at a lower rate, with the understanding (in writing) that I would only work on it in between other projects.