Shortly after I started my current job, my company's stock lost some serious value. Less than a year later, I decided to play around with $200 and bought some of my company's stock, thinking that it was a good deal, that I "got a discount". Well, that was dumb, because the stock fell lower and lower and has had a very difficult time showing any sign of recovery, despite my company doing well financially. Last time I checked (several months ago), that $200 was now worth $80 or so.
Sorry to be vague, but just wanted to relay this story. I also get stock grants through my company, but it's denominated in stock quantity, not cost, so it's still free money but it's a pittance and I get the joy of including it on my schedule d and 8949 (first world problems...)(also, the setup is weird). I'd rather just get that in my paycheck so I could dump it in my Roth, but oh well. Lesson learned, fortunately over a relatively small amount. Could not care less about stock picking. If that "opportunity" didn't play out, I can't imagine any other "opportunity" playing the way I expect it to, either.
We're in a black-out window half the year, it seems, so I'm buy-and-hold out of laziness. Plus, I can't quite bring myself to sell at such a low value. Honestly, I wish I'd just suck it up and sell the next chance I get, put it in my Roth, and move on.