"If this trades doesn't go as planned, will I still be able to sleep at night?"
I like the reflective questions that is asked. It gives one a sense of direction and clarity and to come to terms with the reality that is on ground. In my estimation anyone who only trades with a small amount of money may not need to ask themselves questions especially if that is an amount that if it is lost to trading will not be a problem. Also, this question will come up less and less as experience in trading grows. Other questions will then take over. And that could include how they could use leverage in a way that their risk to reward ratio will be balanced for optimal profit.