"If this trades doesn't go as planned, will I still be able to sleep at night?"
If the answer is yes, then you can go ahead. But if the answer is no, then it best not to make that trade or investment.
This is truly a very good question that a trader supposed to ask himself before trading. But someone may not know until the person begin to trade and experience it himself.
It is true that there are traders that may have opened positions and not able to sleep at night and this can affect the traders health.