You've gotta play considering the probabilities, not score things after the fact based on the realised outcome. To a first approximation it's a good idea to no

You've gotta play considering the probabilities, not score things after the fact based on the realised outcome. To a first approximation it's a good idea to not have any significant part of your wealth coupled to your employment, to avoid situation where a failing company destroys both your employment income stream and your investments in a single event. C.f. Enron employees with company stock...