Less Wrong has been significantly influenced by the skeptic movement. This has general been good for the epistemic health of our community, but at the same time we should also worry about whether everything we have inherited is true and beneficial. In other words, we need to apply skepticism to skepticism itself.
It's often good to start with the strengths of a movement and consider how these can also become weaknesses if taken too extremes, so this is what we'll do in this post instead of taking them at face value. The fundamental promise of skepticism is that it will prevent you from being mislead by weak evidence, poor reasoning, social pressure or those who would manipulate you.
The opposite of foolishing accepting weak evidence is being excessively dogmatic in the standards of evidence you require, even when circumstances require you to decide based on inconclusive evidence. A famous spoof article jokes that we don't know parachutes are reliable because we don't have a randomised controlled trial.
Wittgenstein wanted to argue that language is nonsense insofar as it failed to paint a picture or possible pictures of the world (in a particular technical sense). The only trouble was that this claim itself didn't paint a picture of the world. The logical positivists belived that beliefs were defined in terms of the experimental predictions they made, however it is almost entirely false that just now a chocolate cake spontaneously formed at the center of the sun then dissolve and it isn't clear how to define this claim itself experimentally or in terms of mathematics. Behaviourism argued that it was unscientific to ascribe emotions, beliefs or thoughts to humans as we can't directly observe these, which resulted in a greatly crippled psychology field.
Similarly, the opposite of foolishing accepting poor reasoning is being excessively dogmatic in the preciseness of arguments that you need. When talking about ethics, Aristotle argues that, "We must not expect more precision than the subject-matter exists". Some subjects are inherently hard to talk about and expecting too much precision can prevent us talking about it at all. One example is when people dismiss philosophy as too vague to be useful and then end up effectively adopting a philosophical theory anyway, but without any deep thought or evaluation.
Similarly Kieran Healy argues in Fuck Nuance that demanding more nuance can be a lazy response. He worries than you can almost universally proclaim, "But isn't it more complicated than that?" or "Isn't it really both/and?" or "Aren't you leaving out [X]?". Theorisation requires some level of abstraction and simplification and the demand for nuance interferes with this.
Additionally, we should expect that not everyone will have the capacity to produce solid reasoning even when their ideas are correct. Some people are better at discovering new ideas, while other people are better at filtering them. Some people are good at both, but these are relatively few. If we only learn from strong filterers, we miss out on the ideas that are still on the creative edge. I resonate with Jordan Peterson's characterisation of good art as expressing that which is important, but which cannot yet be fully expressed.
Many communities have knowledge embedded in traditions that derives from long and hard practical experience. These arguments are persuasively discussed in Seeing Like a State and The Secrets of Our Success.
Then there is the issue that those who are less educated or who are non-native speakers are likely to be less able to provide arguments up to a particular standard independently of the truth of their claims. Some people suggest we respond by not applying any significant scrutiny to the truth claims of those who are more marginalised, but my suggestion is solely that we approach these with more care.
The opposite of being excessively resistant to social pressure is being contrarian and adopting non-standard positions so that you can differentiate yourself and signal your ability to think differently. But it's also a mistake to completely disregard social evidence. What people believe provides some level of Bayesian evidence, but beyond that, no-one has time to evaluate the evidence for everything. Even if it were possible, it would almost certaintly be worse for your own well-being. It can be hard not to engage in this impossible task as the alternative is admitting that you believe thesis X because simply you were told it and not because you've made up your own mind.
But beyond this, it can lead to the bad habit of turning everything into an argument independently of how unpopular a view is. Social capital is limited, so it's important to spend this wisely if you want to have influence.
The opposite of being naive is being too distrusting. It can be very easy to identify one or two circumstances when a particular person or organisation lied to you or misled you and then refuse to ever trust anything they ever say again. This may be reasonable if we avoid them without any significant costs due to our circumstances, but this isn't always possible.