Collect as many lottery tickets as you can - Ada Yeo

The most important decision-making principle that I know of is to collect as many lottery tickets as you can, then double down on the ones that start paying off. Many people have written about the importance of maximizing optionality and serendipity in life. The two most influential reads for me have been: Your life is driven by network effects, James Currier Antifragile, Nassim Taleb Principles are powerful because they can help simplify complex decisions with many variables. I’ve applied this particular one to decisions both large (“Should I move from Singapore to Silicon Valley?”), and small (“Should I go to this dinner party tonight even though it’s inconvenient?”). Not all lottery tickets are equal. The best ones have capped downsides, and uncapped upsides. Nassim Taleb calls this “Convex Tinkering”, which he defines as making “low-cost mistakes, with known maximum losses, and large potential payoff (unbounded)”. A prerequisite is having enough context to form a probabilistic asse

The most important decision-making principle that I know of is to collect as many lottery tickets as you can, then double down on the ones that start paying off. Many people have written about the importance of maximizing optionality and serendipity in life. The two most influential reads for me have been: Your life is driven by network effects, James Currier Antifragile, Nassim Taleb Principles are powerful because they can help simplify complex decisions with many variables. I’ve applied this particular one to decisions both large (“Should I move from Singapore to Silicon Valley?”), and smal