Don't beat yourself up about it. We all should have bought google in 2006. We all knew we should, and we all didn't. Same scenario.So like many public companies my employer has trading windows where employees are allowed to buy/sell company stock. These windows last for just a couple of weeks 4 times a year. For the past few years I had some inheritance money sitting in a IRA money market fund just because I really wasn't sure what I wanted to do with it and didn't need to bother with RMD's. Last summer I was thinking that I should just plow it all into company stock, but I got distracted by death of a pet and consequently missed the trading window. The last trading window was in mid-November and prior to it opening up a hedge fund took a huge position driving up the stock 3x and has since gone up 8x. I missed a once in a lifetime opportunity and I'm absolutely sick about it. Unbelievable.