1/ Rethinking optionality.
2/ At the most basic level, optionality just means having lots of options.
3/ If you develop a skill with many possible job opportunities, you have more optionality than someone who develops a skill that only has one or two job opportunities.
4/ As the world grows increasingly difficult to predict, optionality becomes more and more important if you want to thrive in spite of not knowing the future.
5/ You simply see what happens and exercise whichever option turns out to be most advantageous.
6/ In Nassim Taleb’s words: 
7/ When I first read Taleb’s work, optionality made a tremendous amount of intuitive sense to me.
8/ It’s clear to me looking back on my life choices that optionality has been a defining component of those choices.
9/ I have begun to rethink that position.
10/ The modern world has a certain lottery ticket mentality created by the existence of these “optionality opportunities” - capped downside but uncapped upside opportunities like financial options and startups.
11/ Because its possible to make "fuck you money" while risking relatively little then you are more encouraged not to take care of stakeholders.
12/ After all, once you get to fuck you money you're going to be on a beach sipping mai tais.
13/ The world has never been this asymmetrical before. No year is so good for a farmer that they reach "fuck you crop yields" and never have to farm again.
14/ In The Evolution of Trust, @ncasenmare demonstrated that you need the repeat interactions more common in low optionality environments to build healthy communities - ncase.me/trust//
15/ The farmer knows she will need to rely on her neighbors and stakeholders in the future. Her kids likely will as well and so she is inclined to take care of the community and seek out win-win arrangements.
16/ The dream of “fuck you money” is the dream of total isolation and lack of reliance on others. If that is the goal, why does it surprise us that we feel alone and isolated? The goal is explicitly to be be alone and isolated.
17/ On an individual level, the over pursuit of optionality can simply be a way to hide. By always “collecting optionality,” you are avoiding making choices and taking real risk, opting instead for collecting safety nets.
18/ The purely optionality-focused entrepreneur or freelancer then is just the same as the "corporate employee” role they tried to escape - they are bound by fear and unwilling to take real risks.
19/ Optionality is a means to an end, not an end of itself. To put soul in the game is to give up optionality and take on risk in the name of being fully alive.
20/ You can't take the chips with you when you go. They're made to be risked.
