Optionality. One of the most underrated concepts of life I think. The very simplest defintion can be described as by Taleb: being able to accept both outcomes, to be comfortable with the counterfactual. It’s opposite? The Squeeze. The Japanese understood this through wabi sabi- incompleteness. The Taoists knew it when Laozi discussed the empty bowl. Being incomplete means being open to the infinite. A fractal has infinite length because its sides never converge to a complete shape.
Nidhal Selmi posted on twitter once (@imleslahdin) about how there is good in having optionality between school systems for kids. Why bother arguing whether home school, or public school, or private boarding schools are the best if you can CHOOSE which to go to? The reason why utopias become dystopias is because utopias are a SQUEEZE. You don’t get to choose any other option but the ones laid in front of you, the supposed "best".
IM Emory Tate, the chess player known to make even Grand Masters check under their beds before going to sleep, was renown for his remarkable tactics in chess. A complete maverick in the game and off, the man was ready to sacrifice a queen if it meant putting his opponents in a squeeze. While I learned of him only recently, this philosophy I understood even as a child when I competed in chess clubs. It never mattered how disadvantaged you were, by how much you were losing. The squeeze was always a possibility, and keeps your opponent on their toes. Actually, there is another side to Tate. Being an IM (when clearly his skill level was a GM) meant he was free to not care about his status in the chess world. While other GMs held high egos and acted like celebrities, Tate held free chess lessons for local kids, and frequently interacted with his fans. He was in the Armed Forces, knew several languages, and had been to several countries because of his occupation. By being in both worlds, he was free of both.
This situation is extremely interesting when you see who else "sits on borders". Paul Skallas, the man who discovered the color blue, has optionality on Twitter by being employed off of it. And I believe by the same position, he is free of his employment in some ways, knowing he has a following on twitter and can even make some money off of it. Being in two worlds at once, he becomes free of them. However, just like an empty bowl that gets filled, as soon as he loses his job, he loses this optionality, and becomes squeezed, either to look for a new one, or to pursue his twitter career.
Taleb’s definition of free: to stand outside all hierarchies. Bruce lee’s definition: Absence of stereotyped technique as the substance. The two definitions are one and the same. To be free means to not care of peer perception, to be what is so sought after- authentic. And the only people who are able to are those who are outside all hierarchies, who have optionality, material or mental. By being incomplete, you never converge, and when you never converge, you are infinite.