One of my favorite books Epistemology and Psychology of Human Judgment by Bishop & Trout [0] argues that humans are bad at making judgments, and what we want is reliable methods for arriving at truth.

The authors of the book provide several heuristics that yield better outcomes than typical strategies people use.

With respect to probabilities, since humans, on average, suck at it, they recommend a "frequentist" approach. A great illustration is one about a 99% accurate medical test that claims a patient is positive. The probability the patient has the disease is not 99% (over 60% of Harvard doctors get this question wrong). The authors show how reframing the question with a sample population (10,000 people for example) and the relative prevalence of the disease (and noticing the false negatives) the problem becomes almost trivial to calculate.

[0] https://www.amazon.com/Epistemology-Psychology-Judgment-Mich...

In Epistemology and Psychology of Human Judgment [1] the authors recommend a similar approach:

1) Make a point estimate 2) Imagine that you're wrong (what direction are you wrong?) 3) Make a second point estimate 4) Average the two

Excellent advice from an excellent book!

[1] https://www.amazon.com/Epistemology-Psychology-Judgment-Mich...