My life probably looks quite strange to most people. I suspect this is because I don’t play by rules that make no sense to me. I used to do gymnastics, so I grew up in a world that was full of rules. Some made sense: straighten your legs, point your toes. Some didn’t: you’ll get deducted if your bra strap is showing or if you wear nail polish to a competition. I do think it was probably a good thing for me to be in an environment that demanded so much compliance and discipline from me, though—a nice complement to my generally oppositional, pretty rebellious nature. I was always a bit of a “bandita” as my grandmother would say: adventurous, a bit zealous, someone who marched to the beat of her own drum. I managed to rein this aspect of myself in for the better part of my youth; I fit nicely into the systems I was in, I focused on doing well to maximize the opportunity and optionality I would have when I got to the point where I could make choices for myself, that would determine what my life would look like as an adult. Eventually though, I realized that the optionality I was so focused on generating was not going to be worth much unless I figured out what it is that I truly wanted out of life.
Even when I was young, I was overly skeptical of the ideas that were prescribed to me, interested in finding a better way of doing things. I guess that made me a challenging athlete to train and an unruly mind to mold for the systems I was in (I have a distinct memory of being 6 years old, and holding my pencil in a way that infuriated my then-teacher, who desperately tried to convince me to hold my pencil like everyone else did, forcing me to use one of those foam pencil-grip trainers which I HATED. I still hold my pencil the same way. Oops). Fortunately for me, this predisposition towards skepticism and individual thinking that likely frustrated the adults around me when I was a child has made me pretty good at getting what I want as an adult.
self-efficacy
There is a famous story in my family that my uncle tells all the time: I was on a camping trip with my family, and he found me sort of strolling through a field alone at night. I was 3 years old at the time (a particularly small three year old at that). Naturally, he asked me where I was going. I told him I was going to the bathroom. When he offered to accompany me there, I apparently looked at him, brows furrowed, offended by his suggestion, and exclaimed “I go myself!” I then stormed off into the night, sans flashlight, wading through grass that extended well above my head, determined to set out on my mission alone. Some say that your personality is innate to you as a child. Perhaps my fate was already sealed by then: that whatever I wanted to do in life, I would try to first do it myself, without help, without rules, and trust that I would arrive where I was meant to at the end of the journey.
This inclination towards self-sufficiency and self-trust has generally served me quite well, because it turns out that most rules are Bad. Bad rules = rules that don’t make sense. They don’t serve a useful purpose; they don’t create order in a way that is constructive to the collective, or to the individual. Most rules are Bad because if you pay enough attention, you can derive your own axioms that make a lot more sense and will get you a lot closer to where you actually want to go. You can explore what the Bad rules fail to account for, and in the process, arrive at better conclusions yourself.
I tend to be pretty suspicious of rules that others take for granted. I’m always asking them: Really? Why does it have to be done this way? What if you did it differently? I ask myself those same kinds of questions as often as I can, interrogating myself as to whether I even want the “prize” that lies at the end of the game I am playing. The way to do this, as I have observed it, is to get feedback from reality, instead of imagining or thinking yourself into a solution (which rarely works). Good rules are derived from trying, from experience, from the direct feedback you get from the world, instead of from consensus, social approval, or pure theory. You can then trust your rules more, because you have tested them yourself.
Mini tangent: My vestigial venture capital self also feels inclined to point out that the best companies adopt this same philosophy in building successful products; they study how their customers actually behave, not how they think their customers should or would behave. They study what their customers’ problems truly are, and how they actually use and respond to the products they build for them. They rely on feedback from reality to guide their decision-making— they don’t convince themselves that They Know Better, that their customers are somehow Wrong and that they are Right. Having the humility to know that you might always be wrong, that Reality has something to teach you, is how you Win in the real world. Thinking you’re Right, even if Reality proves you Wrong, is how you Lose.
status games are built on top of Bad Rules
One of the things that has always disturbed me about the classic status-seeking path was that everyone a few rungs above those entering the game seemed unhappy. I remember thinking: it’s kind of weird how all of my smartest friends are going after each other’s throats, trying to get these same jobs that people only seem to want before they get them, and are then miserable being in two years later. Cue: this meme, which is perfect.
But no one wanted to hear this skepticism! I remember writing a full essay about this phenomenon then, outlining what seemed to me like straight-forward deception of talented, high-potential young people, portraying prestigious jobs as something they were not, convincing ambitious, hungry minds that it was a huge trophy to get one, only to impose a tremendous amount of suffering upon them when they started them, thrusting them into a vicious cycle of steep earning coupled with even steeper spending and an emphasis on materialism and luxury that was quite challenging for most people to break out of… it all just didn’t make sense.
I ended up holding myself back from publishing that essay as I had initially wrote it, and posted a sort of diluted version of it at the time, because I was afraid that this essay would ruin future career prospects if I eventually changed my mind, which is funny in hindsight, because any career prospects a piece like that would ruin is not a career I would ever want. My hesitation to publish it also stemmed from this sense that everyone was unwilling to be challenged, so convinced that what they thought was Right, unwilling to believe that they had been told to play by Bad Rules.
I now see that people just desperately wanted the Bad Rules to make sense, to be true! Because otherwise: what were all of the sacrifices they had made to play by those rules for? Plus, who wouldn’t want to believe that the rules you’ve been playing by your whole life have your best interests at heart? Isn’t that what they’re there for? But no, those rules are not optimized for your own individual thriving, and it is actually quite safe (optimal in fact) to break them. Because Bad rules ultimately take you to places you probably don’t want to be!!!!!! And most of them are entirely arbitrary! In other words, you can develop a sense of what you truly want, and go after that instead of what people tell you that you should want.
I go deeper into this topic in my essay why i quit status games, with the gist of that essay being: when you realize that peak intelligence is just getting what you want out of life (a la Naval), it becomes impossibly stupid to continue climbing a status hierarchy just to signal to others that you are Smart, when anyone who is actually smart (by the definition I just cited) won’t think that doing so makes you very smart. In other words, your status signal will be relatively worthless in the Right circles, and highly valuable in the Wrong circles. I am speaking in harsh binaries, like Right and Wrong, because binaries are useful; I know that there is nuance and grey areas and blah blah blah. But for the sake of simplicity and concision, I am going to categorize thinking for yourself as Right/Smart, and trusting others to think for you as Wrong/Stupid.
Of all the logical flaws I found in these systems though, what confused me most was how almost no one was thinking for themselves about what they truly wanted! It’s like: how could you even follow a set of rules or axioms if you don’t know that the destination (or more importantly: the journey) they are guiding you towards is something you genuinely want? What good can rules do for you if you aren’t thinking about the game they’re made for and the prizes dangling at the finish line of that game? I now see the unfortunate lagging evidence of this riddled all over the lives of those around me. Peers who were told that they are Smart so they should become Doctors, Lawyers, or [insert prestigious, highly-credentialed career path that sounds impressive to your relatives but takes 5-10 years to arrive at any comfortable degree of freedom inside of] are now having to deal with spending some of the best years of their lives being sleep deprived shells of themselves, considerably delaying plans to start families to coincide with demanding training and education timelines, and having no real path to Freedom except trading time for money indefinitely.
Don’t get me wrong, I’m incredibly grateful for doctors (especially my brother who checked that box off for my parents so I could be an Internet Writer), and I know that some people genuinely are fulfilled by and inspired by what they do, I just think we should encourage a little more free thinking in the Youth. And to remind people that they “pay” for prestige with the lived experience of their day to day life. Status isn’t free; it costs you your time and energy being locked into systems that demand you follow their (often Bad) rules, basically forever.
And honestly, I just want us all to be better, happier, living in closer alignment with what we truly want. I want us to think more clearly, to live more freely, and most importantly: to trust ourselves when what everyone is doing seems a little… off. When it doesn’t seem to make sense. We all need to start asking ourselves a little earlier, a little more earnestly, and a little more frequently: am I truly getting what I want out of life? And if the answer is no, get in the practice of doing something about it! Break the rules! Try stuff! You have agency, and hopefully, if you’re reading this, a lot more freedom than you might want to admit. Use it to do something that feels genuinely aligned with you, that you actually want to be doing. Or don’t. Whatever. I just want more people to notice that most rules are arbitrary, and if they want, they can probably break them, and go in a new direction that appeals to them.
You can thrive, guys! It’s just a matter of getting good at noticing Bad rules (by noticing when they lead to a life where people don’t actually seem to be Winning/getting what they want out of life, and/or when they take you on longer than necessary routes to the same places that you can get to without those rules). And then, when you notice those flawed rules—wisely, thoughtfully—break them. At least, this is what I have been doing for the past decade or so, and it’s working pretty well so far.
Related essays: why i quit status games, returning from the hero’s journey, ambition as a fingerprint, becoming yourself is a process of reduction, on self-trust, comfort. get out of your head
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Love this: “Status isn’t free; it costs you your time and energy being locked into systems that demand you follow their (often Bad) rules, basically forever.”
The part about chasing jobs you only want before you have them and being on an infinite trade time for money treadmill is scarily accurate of almost every corporate job I’ve worked.
“if the rule you followed brought you to this, then of what use was the rule?”