“I can never be all the people I want and live all the lives I want. I can never train myself in all the skills I want. And why do I want? I want to live and feel all the shades, tones and variations of mental and physical experience possible in my life.” — Sylvia Plath

Optionality: the nature of accepting the possibilities of the unknown, to give every fractal self a chance to live. I’d much rather know, but then again, not-knowing keeps all the possibilities open. It keeps all the worlds alive. Source

”This individual has merely acquired stamps of approval and has acquired safety net upon safety net. These safety nets don’t end up enabling big risk-taking—individuals just become habitual acquirers of safety nets. The comfort of a high-paying job at a prestigious firm surrounded by smart people is simply too much to give up. When that happens, the dreams that those options were meant to enable slowly recede into the background. For a few, those destinations are in fact their dreams come true—but for every one of those, there are ten entrepreneurs, artists, and restaurateurs that get trapped in those institutions.” — Mihir Desai on Optionality

As humans, we tend to love ‘exploring’ our possibilities more than ‘exploiting’ and diving deep/committing to what we already have — we lean heavily toward explore in the exploit explore tradeoff curve.

This is the optionality fallacy.

In a life like the one we live in where cause and consequence is extremely hard to distinguish due to the huge number of confounding variables, trial and error reigns supreme. Though, this doesn’t mean trying everything really quickly and abandoning things if results don’t manifest (ahem, talented kid burnout syndrome)

Tinkering and experimenting is a more efficient investment of your time than following a set path of learning which assumes an intrinsic value in specific skills and ignores the non-linear way life works.

”Accumulate optionality through differentiation, not conformity” recommends Torenberg

Maybe why humans constantly chase prestige: to keep doors open as a means of cross-disciplinary recognition.

Paradox of Choice

Individuals are more likely to be stressed from a larger number of options as considering more choices requires more mental effort.

Requiem for a Dream

New Yorker on Aaron Swartz

“I’ve hired a lot of very talented programmers, and one of the things I discovered was that the people who didn’t graduate from college couldn’t finish projects,” his father says. “Because when you go to college, there’s all sorts of stupid stuff you have to do in order to get through.”

It is a vertiginous thing to have so much freedom—to be always self-skeptical, always testing the reasons for your beliefs, always prepared to abandon them for something better. If you can do anything you want, then every day becomes an existential problem—an empty space of possibility that has no ceiling but also no walls and no floor.

Making the Decision Right

Sarah on Substack

What I’ve come to learn over the past year is that there are two types of people: people who make the right decision and people who make the decision right.

Optimizing for optionality seems like the rational thing to do, until I really looked at my life. I had all these “options,” but I hadn’t done any of them.

I choose the next thing and make it the best.