It's certainly possible. It's a complicated topic. There's a lot to consider and much of it relates to your personal risk appetite and financial position.
There can be very serious tax consequences if the spread between your strike price and the FMV is large enough. The IRS doesn't care that you can't sell shares to pay the taxes. They're still due that year.
That said, you can probably do the math to stay outside AMT by limiting the number of shares you exercise. It's so hard to know whether or not to do that. I imagine a lot of employees felt pretty good about their WeWork options at the beginning of this year. I imagine. I don't know anyone there.
There can be very serious tax consequences if the spread between your strike price and the FMV is large enough. The IRS doesn't care that you can't sell shares to pay the taxes. They're still due that year.
That said, you can probably do the math to stay outside AMT by limiting the number of shares you exercise. It's so hard to know whether or not to do that. I imagine a lot of employees felt pretty good about their WeWork options at the beginning of this year. I imagine. I don't know anyone there.