I'm leaving my job in soon and I'm sitting on a significant amount of company stock. It's volatile, so I want to unwind about 50% this year and the rest next year. I have some remaining vested ISOs that will need to be exercised soon before they expire. I'll probably HOLD 10-20% for the long run even though that's contrary to my mostly bogleheads approach. Taxable income will likely dip this year cause of new 1-yr vesting cliff.
My plan so far:
* My plan is to sell roughly 5% (by share count) a month to DCA out of it.
* I won't sell any losses till 32 days after my last exercise.
* I'm only going to sell exercised ISO after they've reached Long Term status, probably same for RSUs as well
My lots are a total mixed bag—a few are underwater (losses), some have significant gains. Overall, 57% gains. It's a mix of short and long term holds.
Questions:
1. What's the optimal order to sell these specific lots?
2. Should I prioritize clearing the losses first to offset gains later?
3. Should I prioritize selling most gains or least gains first?