Harvest the losses or Donor Advised Fund.

We made over $300k by selling Apple stock, which is more than our combined income. (We work in do gooder fields.) Just lucked out by investing a small windfall in the company and selling at the right time after holding a long time. Ended up paying a shitload of taxes, which was a shock. But our accountant pointed out that we made a lot, so now have to pay a lot— nothing to feel bad about. Congrats!