I am familiar with the Black Swan, yes. Most risk assessment make assumptions about distributions. Then they add assumption to assumption to… that gives you an idea.
Now if you assume bell shaped curves, that works ok, and mathematically is relatively simple. BUT surprisingly, life in the extremes of the tails is NOT bell-shaped, so rare events may or may not be quite as rare as you think. See 100yr floods. The challenge is guessing what distributions look like, and how to validate those assumptions.
[TL:DR] models are good but data is always more variable. Identifying that early is a Good Thing.