Epistemic status: Reference. I’ve used this heuristic for my life decisions for over a decade. This essay introduces it but needs refining, and I would welcome pushback and feedback.

Verse I: Pessimism

We are optionality-optimizing oracles

We seek the future yet never grasp it

We create options only to refuse them

We give ourselves agency and then rob ourselves of it

Prose I: Sentience & Regret

Amongst my friends, we have this running bit, we will often say that “I only gained sentience a year ago.” While the joke is nonsensical, the implication is important. The current version of ourselves seems to only have existed in the present, what I was doing and the person I was over a year ago feels entirely distant, disconnected, and separate from the person I am today. As your set of lived experiences expands and your learning grows, you seek new goals and experiences, becoming a different person, and prioritizing new values. So how might someone future-proof decades’ worth of potentially unaligned actions to prevent unfathomable regret?

 

Prose II: Don’t Go to Prison

Let’s consider some cases when life may force your decision-making, whether you’re ready or not:

  1. One morning, I decide to commit a crime. Soon, I am handcuffed, in jail, and I immediately regret my actions. After months, I gain more life experience and understanding than my pre-jail, pre-crime self, but find myself unable to make decisions. I cannot choose not to commit crimes anymore, nor can I choose where to go for vacation, or choose how to spend the rest of my life for that matter. My learning expanded but my options shrunk immeasurably. My past decision failed future me.
  2. One morning, a charity knocks on my door, asking for clothing donations. I quite like my clothes, but my tastes constantly change, and I don't know which clothes I will value most in the future. To be safe, I politely apologize, keeping my full wardrobe of options intact. I feel bad for not being charitable, and next time, I might draw a different line of when it's worth it to reduce my clothing options. My learning increased, but my options were largely unchanged.
  3. One morning, I am halfway through high school and consider dropping out. I could start working and compounding my income sooner, and I already know some jobs I would enjoy. However, finishing school could open more career paths, and pursuing university could open even more. So I decide to stay, expanding my option set. Fast-forward, I find my calling in academia, and my future, chemical-engineer self is eternally grateful for my high school self (though my unexplored potential-future billionaire, high school dropout-self is pissed). I both expanded my learning and expanded my options. Future me understood more, and with more options, made better choices.

 

These cases depend on two assumptions. First, that as people experience life, they develop greater learnings. Second, that your future self uses these learnings to make better decisions, specifically knowing which values they want to optimize. Exceptions exist, like making bad decisions in a rough period relative to your past self, but people on average trend towards having a larger decision-making toolkit.

 

Generating more options (or at least the same amount) for your future self is valuable because it best enables you to optimize for your future values, even if you don’t know these values now. Therefore, one principle for future-proofing your decisions is seeking whatever adds more options. Or at the very least… don’t go to prison.

 

Prose III: Mo Money Mo Options

If the insight here is simply to expand optionality, then we have a problem. But it seems society has culturally evolved to generate optionality, and if a practice has survived for this long, we should consider why it persisted.

 

Cavepeople had limited options:, (1) do something to survive, (2) die (this is admittedly reductive). As humans developed societies and cooperated, people specialized beyond survival-based decisions. This expanded optionality at a societal level, though day-to-day options stayed limited as you’re still expected to work a job. As we innovated, built better buildings, machined more machines, and improved our knowledge, optionality expanded. Economic and political systems seem to optimize for increasing people’s freedoms (while also supplying societal goods). Overall, optionality increased, whether it was the goal or the byproduct of axioms we set.

 

Money is central to societally increasing options. A chicken farmer in a barter economy can trade eggs, feathers, and meat; but not everyone always wants these, and I must trade them before they perish. After many steps, money developed to serve several uses, and most central to optionality, “a standard of deferred payment.”

 

People want money, the more the better, you can do many things with money. One thing most rational people tend not to do is spend it all at once. They save it, invest it, budget for things they may not end up purchasing, or even set it aside to purchase something for others who didn’t even want that. With the same bill, you can give to a charity, buy a weapon, upskill yourself, gamble it away, and more. Money is partly valuable for the optionality it provides; this is evident from how seeking money is extremely common, and yet people’s uses for it are extremely diverse.

 

Money is not the terminal value, but helps pursue what you do want to optimize for. If you’re only seeking money, it would be wise to step back and ask why you really want it, maybe it’s not for the options it opens, but for other benefits like prestige.

 

Optionality is closer to the terminal value than money. To future-proof your decisions, seek to improve your “option wealth,” rather than actual wealth. While those may often coincide, sometimes they won’t. But if you are stuck trying to choose what maximizes your options in practice, the capitalist in me says money is a fine heuristic. More money often does equal more options.

 

Prose IV: We Can’t See the Future

If we are blindfolded when it comes to seeing the future, how do we know what choices maximize our future options? You can think about it like an investment. Since life always presents you with decisions, then any choice, even making no choice, has opportunity cost. Seek to maximize options gained for the least options given up. Most investors balance reasonable risk for commensurate returns, but wouldn’t forego either for the other. Therefore, you want to maximize the risk-adjusted option wealth.

 

Seeing the future would help us make optionality-optimizing decisions, and prevent unfathomable regret. But people still regret choices that added options, and also choices that removed options. But life forces you to make choices, and optionality-optimizing seems the best way to go. More options enable greater agency. You would be frustrated if someone took away your options for how to spend the day, yet we constantly allow our past selves to limit our own options without consideration for who we are today.

 

Seek to make decisions more intentionally and agentically, and when you do, consider future optionality as a decision criterion. Human society trends towards optionality-optimizing behavior, and as a human individual, you should strive to be an optionality-optimizing oracle. Using optionality as a decision-making heuristic is a beautiful way to exponentially improve your life, even without prescience.

 

Verse II: Optimism

A life led, a life lost

I see the future, a world I crossed

Options as a heuristic, I optimize

Increase future choices, one must surmise

Options as dimensions, an improved prism

Above all else, don’t go to prison

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2 comments, sorted by Click to highlight new comments since: Today at 8:19 PM

Sounds like regret aversion?

edit: Hm, you're right that optionality is kind of an independent component.

I'd be curious what would a situation be where your learning would remain unchanged but your options would increase, are those just cases where you just get lucky in life? you just stumble upon something and you don't really absorb/increase the learning that could have happened? lmk if this is a silly question but it was just something that popped into my head. 

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