The problem with scoring a big payout is that it likely pushes you into a higher income tax bracket.
“Front-loading a donor-advised fund can be a great way to offset income,” said Alexander Gross, a certified financial accountant and certified financial planner at Daintree Advisors in Boston.
You can donate a big chunk of money into a DAF, grab the deduction this year, and take your time making grants out to charities. For example, if you typically donate $10,000 a year to charity, you could put $50,000 into a DAF this year, grab the tax deduction right now and then make $10,000 in grants over each of the next five years.
(A bit of IRS housekeeping: When you donate an appreciated asset, your deduction is limited to 30 percent of your adjusted gross income for that year. There’s a five-year “carry forward” rule that allows you to keep writing off the donation in subsequent tax years.)