[rajacombinator]

It all depends what you consider scary.

There were the times when I happened to be the only person running the trading desk during the nights of the Bear Stearns, Lehman, and FNM collapses, having to turn over a ~$2B portfolio. It was all OPM, so not personally scary per se, but staring into the abyss definitely altered my worldview.

Then there was the time we thought a stupid bug I made cost the company $500k. Turns out it was only about $5k, but man I still cringe with embarrassment when I think about it. Guess I didn't learn my lesson though because I still make stupid bugs now and then.

The thing that really made me toss and turn at night though was being stuck in dead end jobs with no potential for upward trajectory or recognition of my contributions. That's the scariest thing that can happen to a career.