Pessimism vs Skepticism

Being skeptical is important to manage risk but pessimism is a choice which may affect your future prospects.  Pessimism is a state of mind, a negative lens, which may lead to exaggerated risk-reduction.
How do you bridge the gap between skepticism and an informed decision?  Checking references, verifying statements and conducting experiments.
Some people have become pessimists, which leads to limited risk-taking because they are paralyzed by FEAR (false expectations appearing real).
Humans aren’t the best at assessing risk vs. reward and making an optimal decision. Perhaps AI will help humans more intelligently take calculated risks.
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