The Most Important Decisions In Life Are Not Rational
The most pivotal choices that face you cannot be made rationally. When it comes to assessing transformative experiences, you *necessarily* lack the information to fulfill criteria of rationality.
Instead of wishing this weren't so or doubling down on decision-making methods that can't work, embrace this absurdity. This state of affairs lays bare how deeply our lives are affected by things beyond our control. The sooner you get over it, the better.
Ordinarily, we think - or hope - that our choices are rational, the straightforward product of available information about our preferences and information about the world. Although we often struggle to clarify our values or to obtain reliable and complete empirical information, those problems are not inherent to rational choice itself. Instead, they're contingent problems having more to do with individual psychology and the particularities of time and place.
But transformative decisions are different. Even if you have full information about your current self and the world as it is, you can't now compute what your future (transformed) self will think about the outcomes on the table.
In other words, transformative decision making is essentially garbage in, garbage out. When we make transformative decisions, we have only semi-irrelevant information to go by (like what *other* people now report about *already* having been transformed in this way). Thus, our choice is necessarily uninformed.
You can kind of force transformative choice into the mold of regular rational decisions by starting with what observing what people choose and inferring their preferences from there. This is basically a reductive behavioral view, based on the idea of "revealed preference."
But this revealed preference approach doesn't generally match the qualitative experience of transformation. Even if people end up happy with their decisions to marry, have kids, take drugs, travel, or whatever, they commonly notice that aspects of these changes were completely unforeseeable. The transformed finds that her post-choice self is different in kind from her pre-choice self, on account of what has been revealed to her through experience. It doesn't make sense to say that the pre-choice person had a full-fledged preference for the outcomes she necessarily couldn't foresee.
We can't understand the value of revelation as a regular preference within the ordinary choice model, though. It's not plausible that people have strong preferences *literally for having novel experiences per se* - no matter the cost or consequence. An ordinary preference for novelty is more often domain-specific, with limited downside and upside (i.e. you love trying new restaurants, but some of them suck).
Plus, undergoing some kinds of revelation preclude others, because our lives are finite and deeply path-dependent. You're not going to have much luck pursuing family, travel, religion, spirituality, extreme sports, etc to transformative degrees all in one lifetime.
So even someone who strongly wishes to pursue revelation as such can't properly peer into the contents of different potentially revelatory experiences to figure out which maximize revelatory value.
The only way forward here is to admit - to embrace - the arbitrary nature of transformative choice.
This fact is absurd, but the realization is liberating. You have trouble making these big choices because they're *impossible* to make in the way you'd like. And of course you have trouble remembering why you made the past transformative choices that you did! You're not really the same person as you were when you were making them, so your past reasoning is slippery and difficult to conjure.
These transformative choices aren't irrational, but neither are they rational. Transformation, to the extent we can choose it, lies outside the sphere of rationality altogether.