We make an average of 35,000 decisions everyday and automatically assess most without paying too much attention. Getting out of bed, opening the doors, deciding what to say when talking to people, etc. These decisions normally come with low-upside low-downside outcomes and that's why we don't pay too much attention. Nevertheless, from time to time, there are some decisions that may impact our upside and downside more significantly. In order to optimize the decision we need to carefully assess the upside and the downside:
Ideally the expected upside has to be bigger than the downside (as long as there is no chance of death so you can make another decision)
Avoid death: no matter how much it pays to win at Russian Roulette while you are still young, the downside is death. This comes also when going "All In" when betting or decision making. Although assessments may differ a lot in different contexts, avoiding death should be a general rule no matter the upside.
When safe, you are still may have a negative outcome (incurring into risk) BUT in this case you either Win or Learn but never die.
If this rules is applied repeatedly, and assessed fairly well, the expected value of you decisions in the long run will always be positive.