Two things I wanted to talk about ESPP: personal bias and taxation.
I remember I grew tired of my undergraduate college at the fourth year, due to various reasons. But after leaving my college for so many years, now I think that’s one of the best places I have been. Personal congnition bias also plays with work. There are always misgivings in the work place, this got intensified with the recession. Recent Economist has an article on this “unhappy work place” topic. But if we take a deeper breath, I think many work places are not as bad as we perceive. In fact, some maybe fabulous business if some reform initiatives being applied.
On the other side of the equation, we all know what happened to Enron and WorldCOM employees and retirees when they put signigicant amount of personal wealth on company stocks. They believed in the pep talk of their CEOs.
Taxation is a complicated matter. Some explaination from Yahoo (Turbo Tax).
Appendix: my ESPP history