So...if you were given a bonus in the form of either X stock options or X/4 restricted stocks, what would you take and when would you exercise it?
Let's say the current value of a stock option is $10 and the current value of the restricted stock is $45. If we were to sell now, the X/4 restricted stocks would obviously be the better deal...but...should we sell now? We're in a fairly high tax bracket, so anything we got would be taxed at 28% federal, plus state. SO has been at this company a couple years now and FI is less than three years away. In FIRE we'd be in the 15% Federal bracket. The year we FIRE, we could make sure to do so early on in the year, significantly cutting our tax bill on the bonus.
There's a reason I automate everything else...this type of thing just makes me anxious and risk averse. This bonus is 5% of our NW.