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The Paradox of Loss Aversion and Regret

“In the end, it’s not the things we did that we regret, it’s the things we didn’t do.” (Location 179)

Regret for things not done is interesting when loss aversion is taken into account. Since daily life is spent avoiding pain, it seems paradoxical that at the end of life we fear we haven't done enough. 202212281353

Whatever you decide to do, don’t sell all of it at once. Why? Because of the tax consequences and the possibility of regret if the price skyrockets. If you sell it all right away and it goes up 10x, you will feel far worse than if you sell 95% of it and the remaining 5% goes to $0. It’s this regret minimization framework that you should employ when deciding on how much to sell. (Location 3209)