Psychological studies found that humans have a notorious tendency to think about their environment and feelings in static terms and underestimate how much they will change in the future.
I think part of your question is rooted in this false assumption and therefore not answarable. Life is chaotic and the biggest effects will come from rare, lucky, unforeseeable, "unkown unknown" type coincidences. These are positive/negative Black Swans in Taleb's terminology. Eg. a life-long-friend from a conference, your future wife in a party etc..
What you can do is maximize your surface to these positive Black Swans(eg. hoarding options, meet peoples) and minimize possible negative outcomes(leverage contracts, debts, anything that tides you down).
Reinterpreting your question these types of heuristics/practices are what worth doing, but they are usually not specific decisions.
Books listing similar heuristics are Reed's Suceeding, Munger's Almanach and of course Taleb's Fooled by Randomness and Black Swan. Wonderful books, hope it helps.