I know what the rule is; the problem is figuring out amounts. Bonuses are paid in June. I have no idea what they will be. Because of that, I don't actually know what my withholding will be either. It would be easier if I could wait until after the bonus.
I think I can annualize my income if I scour bank statements and brokerage statements for when interest and dividends are paid. I guess what I could do is do that for the first quarter, compare to my paystubs and make sure I am not under withheld for the first quarter -- except now that I am writing out what I would try to do, I still wouldn't know, bc I wouldn't expect to be withholding 25% of expected tax in either the first or second quarter. Maybe I should do nothing until the third quarter when the bonus is paid out, and then go back and check everything out, because then I do need to be at 75% at a minimum. And then I would have to annualize within Turbotax. I think I am talking myself into this, but also maybe thinking I should get an accountant going forward, I don't know. I am willing to undertake some difficulty to do this (I mean, I probably spent an hour figuring out how to deal with the $300 of foreign tax that came through my international index fund, which should be another thing that it is easier, because that is a very normal and straightforward type of fund to hold!), but it is really hard when I don't have concrete numbers to deal with.
I guess a related lament is why that bonuses are under withheld? Like, at least optionally, why can't they withhold at the same rate as the rest of my checks? I did ask payroll, and they said, no 22% is all they can do. I feel like this should be a common enough issue that I would hear about it from others at work, but I'm guessing if you file married, there is a lower percentage of this happening.
