In November 2000 my options were worth $2.4m on paper but they did not start vesting until January. In January they were worth -$1.5m and never exceeded the strike price again, at a company that is still public and worth > 10 billion today. They laid me off in february. I got healthy in 2 months and found a small startup with a 15% paycut but the CEO was a WeWork-level crook with a jet and he absconded with all the money 8 months later and it failed. I finally got a stable job in mid 2002.