Would have

As the poet John Greenleaf Whittier wrote: “Of all sad words of tongue and pen, the saddest are ‘It might have been.’” “I should have” and “I wish I had” are two more of history’s saddest sentences.

Extremes

"More barbells. Do crazy things (break furniture once in a while), like the Greeks during the later stages of a drinking symposium, and stay “rational” in larger decisions. Trashy gossip magazines and classics or sophisticated works; never middlebrow stuff. Talk to either undergraduate students, cab drivers, and gardeners or the highest caliber scholars; never to middling-but-career-conscious academics. If you dislike someone, leave him alone or eliminate him; don’t attack him verbally."

"...anything that removes the risk of ruin will get us to such a barbell."

-Nassim Nicholas Taleb, Antifragile, p166

Stoicism

"Success brings an asymmetry: you now have a lot more to lose than to gain. You are hence fragile...

An intelligent life is all about such emotional positioning to eliminate the sting of harm, which as we saw is done by mentally writing off belongings so one does not feel any pain from losses. The volatility of the world no longer affects you negatively.

The modern stoic sage is someone who transforms fear into prudence, pain into information, mistake into initiation, and desire into undertaking.

...invest in good actions. Things can be taken away from us - not good deeds and acts of virtue."

-Nassim Nicholas Taleb, Antifragile, p154-156