As it stands, this essay will cause people to insert themselves in the piece along the way rather than consider from a distance what is being discussed. This is especially true since one of the options is framed as the 'good' one, which triggers our innate confirmation bias - of the aspects we recognize in ourselves, we see the 'good' ones loud and clear, while we downplay or ignore the 'bad'. The takeaway of the piece for most is 'I'm an independent thinker' with perhaps some brief acknowledgement of 'but I've had to do conventional things'. Just evoking Dunning-Kruger doesn't innoculate against this conclusion.
One of my favorite quotes is "Be regular and orderly in your life, so that you may be violent and original in your work" by Gustave Flaubert. This is, in effect, and similar but distinct thesis from pg's - that people choose to spend time & energy being 'independent thinkers' in certain domains of life, while hewing to convention elsewhere. Of course, different people do this to different degrees, but that's really where this exploration is most interesting - where, when, and how should I be an independent thinker?.
One of my favorite activities when getting to know someone is to find the part of their being that is the independent thinker - what hidden rebellions they posses, where those came from, etc. Almost every reasonably smart person I've met has had some independent or unconventional aspect to them if you look close enough, even if they're outwardly very conventional. It's finding these gems and learning from them that makes getting to know someone so much fun. To his credit pg does mention something similar when discussing learning from people.
The other reason I like Gustave's quote is that it suggests much more of a choice and strategy in the matter of independence, while leaving open what set of circumstances that led to the 'violent and original' aspect of independent thought. This rings more true to me, because independent thinking has a personal cost when dealing with others, and we must engage with others in life. Reasoning from first principles or holding unpopular beliefs cost us energy (for different people this energy is more or less felt), and Gustave's point is to focus those limited energies on our creative work where they are more productively employed.
Having studied psych, bio, and education I'm sensitive to arguments that pontificate about whether something is 'more nature than nurture', especially from those with very technical and deterministic mindsets. To me, this is lazy thinking and convenient shorthand for 'I don't really know how people come to know things'. It's even contradicted by his own admission that his father gave him a strong dose of one of the three parts of being an independent thinker. Because we have such an overwhelming amount of evidence about how different environments shape people's beliefs and actions, when presented with nature/nurture arguments about loose concepts like 'independent thinking' my take is the burden of proof is on those claiming nature. [1]
Nonetheless, I did enjoy the essay and its analysis. Many parts rung true or rhymed with my own experiences as a founder and early employee. For instance, the increasing conventionality of later employees you hire. But again pg gets close but misses an important nuance - the environment of a startup at founding or early on inspires more independent thinking because it's a blank sheet where people have a great deal of agency, while the environment of a startup after product market fit is a more conventional environment with constraints that drive conventional action. Thus, most people thrust into an early stage environment are going to become more 'independent thinking' by virtue of the environment and visa-versa in late stage environments.
Anyway, it was an enjoyable read regardless, and clearly inspired some quality discussion.
[1] A great example of this is the rise of violent crime in the 70s and 80s. A person then may come to the conclusion that man's nature is much more violent, when in fact the root cause is an excess of lead in the environment disrupting neurological development. This is an extreme 'near nature' argument but worth considering how little we understand our environments effect on us. https://www.motherjones.com/kevin-drum/2018/02/an-updated-le...