This is the really bad part about equity compensation in a publicly traded company. When that stock starts devaluing rapidly it runs past even your "worst" jaded future predictions, and then it is depressing.

Back in 1998 when a company I helped start was acquired by a publicly traded company, and by 1999 the stock price was over $100 and everyone was feeling "super good" about the future. The internal dialog goes something like this, "This may be an anomaly but damn! even if the stock drops to 50% of its value I'm still doing great!."

In my case the stock dropped in value to below a dollar a a share, 99%+ drop. That feels really really horrible, especially if the future doesn't have anything in it that would rescue or recover the value. Even though there was nothing that I personally could have done (legally) to change the outcome, as an engineer and a person who solves hard problems, it made me feel like a total failure. Like I had let down my family, my friends at work, and people who I knew who had bought stock in the company as a sign of confidence in me.

It is really hard to understand that kind of feeling until you've been through it I think.