I've had stock options at four of the companies I've worked for, but I've never made any money off of them... until now. Stock options are supposed to be a great tool for aligning employee interests with the bottom line, but in reality, they're more like a lottery ticket. In my case, they were more like a scratch and win lottery ticket, because I'll be lucky if my gain after taxes is $200. I'm not complaining since these options were set to expire in a couple of weeks and they had been underwater since May.
This experience was reinforced my belief that I don't have the stomach for active stock market investing. I like to make informed decisions, but even if I studied the markets all day and knew how to decipher a balance sheet, over a two-week time span, any individual stock can tank or go though the roof for reasons that no one could have anticipated. I finally decided to just pick a price that looked reasonable but was still high enough that it made me feel like I was still making some money and submitted a limit order. It executed yesterday afternoon near the intraday high and after today's 2.3% drop, the stock is now trading just barely above my strike price, so as it stands, I'm looking like something of a Wall Street genius right now. Unlike a compulsive gambler, instead of feeling a rush from all of this, I'm just glad that it's over and that I have a little bit of extra cash in my pocket.