Suppose one has done work of some value for a charitable organization in exchange for money. This organization would normally qualify as a destination for tzedakah, and perhaps you have also given this organization money in the past. Now one of the following situations arises:
- You tell the organization to keep the money as your donation to them, since this will lower your marginal tax rate (in the U.S., this donation would not count as income, but may bump you up to a higher income tax bracket, which would increase your tax liability on income from other sources).
- The organization asks to keep the money as your donation to them, since this will reduce their payroll tax obligation, and you consent.
- You agree ex ante (lechatchila) to accept a lower hourly wage than what you charge other non-tzedakah organizations for identical work, with the difference being an effective donation.
- You agree ex ante to accept a lower hourly wage than what your peers are charging this same organization, because you are more wealthy than them and can afford to give the organization a larger donation of your time and money. However, you do not do similar work for non-tzedakah organizations, so there is no true reference for how much the work is "worth."
In which, if any, of these situations can you count the forgone income towards your ma'aser kesafim obligation?
Note the two situations above may or may not differ in that 1-2 are ex post (b'diavad) agreements, and 3-4 are ex ante (lechatchila).