A good friend of mine, James, is an unemployed graphic designer with a significant amount of time on his hands.
I really like his work and would like to commission him at his desired rate. However, I've asked him casually (although I did specifically mention that I would pay him his going rate, no more, no less) before if he would be interested and he said "No" in a very casual way.
I understand that he has no obligation to do this work and that I should respect his decision not to do work for me, but this seems to be a win-win for the both of us and I'd really like to convince him of this.
I also understand that situations like this can lead to awkward interactions. Dealing with significant sums of money, having to put time aside between us to work "professionally", and the risk that I don't like the work he's done could be reasons behind him denying the casual request.
The main drivers that make me want to specifically work with him are:
- His style is something I desire
- He has done free/work as a student for me before which the work I am commissioning would be based off of
- I would expect we could have a good working relationship since we talk to each other often, potentially making the process more "fun" for the both of us
- I want to support him in his career, especially since he is currently unemployed
How can I ask/convince him to do this work for me? Or at the very least, how can I ask him in such a way that he might give me a very specific answer as to why he wouldn't want to do this?