Because of the specifics of my tax situation, I really need to sell a large number of shares in the 2021 calendar year, and tomorrow (17th) is the last day before our company’s blackout hits. There’s so many shares involved that even a small uptick in price (likely to happen EOY) will mean a large amount of money for me. I’m seriously considering quitting now so I can sell between Dec 20-31st. Would this work? Or will it take too long to process?
If you quit during blackout, you need to wait till trading window open to sell.
Huh? Blackout periods don’t apply to ex employee unless it’s different for different companies.
What do you know that we don’t know?
In theory the day after your last day. If you're not an employee then the trading window does not apply. Unless someone can prove you have insider information you should be good to sell.
Depends on whether you have insider information. If you do, you need to wait until it's public, like the next quarterly report. If you don't you're clear. Blackout periods are company policy. The actual law is simply no insider trading.
Can you not borrow against other equity assets if you need cash that desperately?
How much tax savings are we talking about that seems big enough to affect your career decision? BTW, Santa Claus rally is never guaranteed.
Next day.
It does . Else people will just quit to commit frauds