Gwern is amazing and what a fascinating website. I hear you and understand where you are coming from, but some people thrive under extreme organization like this. These are the kind of people I want writing technical documentation on my teams.
The ability to wield the power of the Internet to answer questions, not just optimizing a shopping cart, but the ability to answer deep questions is a needed and important skill.
I have zero issue if someone wants to optimize themselves, even with no other end other than "optimal".
I am all for being the best person we all can be -- but Gwern seems to have made personal optimization the end goal itself.
I think we should aim to be happy well adjusted people, not work ourselves to death, not drug ourselves to our physical limit.
There were times in my life when I behaved similarly and it was rooted in deep dissatisfaction with life.
To be clear, this is not an ad hominem attack. The article is amazing.