A distillation of what @naval said on Clubhouse last night:
What you call chaos I call spontaneity.
A regimented life is like a heartbeat that's non-chaotic; it's a system that’s too ordered. It doesn't have any life to it. And real life has lots of ups and downs, some of them very extreme.
I over-plan, but planning is pretty useless. What tends to dominant life are a small number of Black Swan events in both directions, positive and negative.
Expose yourself to asymmetric upside and lots of good options: things that can become massively important for you.
And you want to avoid the asymmetric downside: anything that can end the game, whether it's through financial ruin, or reputational ruin, or physical ruin.
That requires a certain amount of chaos and spontaneity.
If nothing else, 2020 taught the power of optionality.
We think about planning as linear and controlled, but that's not how the world around us works anymore.
The world is dominated by nonlinearities, so understanding options value is far more important.
