Epistemic Effort: I've thought about this for several weeks and discussed with several people who different viewpoints. Still only moderately confident though.

So, I notice that people involved with the rationalsphere have three major classes of motivations:

Truthseeking (how to think clearly and understand the world)

Human/Personal (how to improve your life and that of your friends/family)

Impact (how to change/improve the the world at large)

All three motivations can involve rationality. Many people who end up involved care about all three areas to some degree, and have at least some interest in both epistemic and instrumental rationality. And at least within the rationalsphere, the Personal and the Impact motivations are generally rooted in Truth.

But people vary in whether these motivations are terminal, or instrumental. They also have different intuitions about which are most important - or about how to pursue a given goal. This sometimes results in confusion, annoyance, distrust, and exasperated people working at cross purposes.

Terminal vs Instrumental Truth

For some, truthseeking is important because the world is confusing. Whether you're focused on your personal life or on changing the world, there's a lot of ways you might screw up because something seems right but doesn't work or has a lot of negative externalities. It's necessary to do research, to think clearly, and to be constantly on the lookout for new facts that might weigh on your decisions.

For others, truth-seeking seems more like a fundamental part of who they are. Even if it didn't seem necessary, they'd do it anyway because because it just seems like the right thing to do.

I think there's a couple layers of conflict here. The first is that instrumental-truthseekers tend to have an intuition that lots of other things matter as much or more than truth.

It's more important to be able to launch a startup confidently than to have an accurate perception of its chance of success. It's important not to immediately criticize people because that disincentivizes them from trying new things. Interpersonal relationships seem to need 5x as many compliments as criticisms to flourish. It's important to be able to run a successful marketing campaign, and even if you're trying to run an honest marketing campaign, comprehensive honesty requires effort that might be better spent on actually building your product or something.

It may even be necessary to schmooze with people you don't respect because they have power and you need their help if you're going to make a dent in the universe.

Then, there are people (who tend to be terminal-truthseekers, although not always), who counter:

Earnest truthseeking is incredibly rare and precious. In almost every movement, it gets sacrificed on the altar of practicality and in-group solidarity. Can't we just once have a movement where truthseeking is the primary thing that never gets sacrificed?

This doesn't just seem worth trying for the novelty of it: the world seems so deeply confusing, the problems it faces seem so immense and so entwined with tribal-politics that distort the truth, that we probably need a movement of impact-oriented truthseekers who never compromise their intellectual integrity no matter what.

I find this argument fairly compelling (at least for a deeper delve into the concept). But what's interesting is that even if it's an overriding concern, it doesn't really clarify what to do next.

The Trouble With Truthseeking While Human

On the one hand, social reality is a thing.

Most cultures involve social pressure to cheer for your ingroup's ideas, to refrain from criticizing your authority figures. They often involve social pressure to say "no, that outfit doesn't make you look fat" whether or not that's true. They often involve having overt, stated goals for an organization (lofty and moral sounding) that seem at odds with what the organization ends up doing - and if you try to mention the disconnect between what people are saying and what they are doing, they get upset and angry at you challenging their self-conception.

The pressure to conform to social reality is both powerful and subtle. Even if you're trying to just think clearly, privately for yourself, you may find your eyes, ears and brain conforming to social reality anyway - an instinctive impulse to earnestly believe the things that are in your best interest, so you peers never notice that you are doubting the tribe. I have noticed myself doing this, and it is scary.

In the face of that pressure, many people in the rationality community (and similar groups of contrarians), have come to prize criticism, and willingness to be rude. And beyond that - the ability to see through social reality, to actively distance themselves from it to reduce its power over them (or simply due to aesthetic disgust).

I earnestly believe those are important things to be able to do especially in the context of a truthseeking community. But I see many people's attempts as akin Stage 2 of Sarah Constantin's "Hierarchy of Requests":

Let's say you're exhausted; you want to excuse yourself from the group and take a nap.

In stage 1, you don't dare ask. Or you don't understand why you feel shitty, you don't recognize it as fatigue. You just get more and more upset until you collapse in a heap. In stage 2, you rudely interrupt people in the middle of something important and announce that you're tired and you're leaving. In stage 3, you find a convenient moment, apologize for cutting things short, but explain that you've got to get some rest. In stage 4, you manage to subtly wrap things up so you can get some rest, without making anyone feel rushed.

It's better to be able to rudely criticize than not at all. And for some people, a culture of biting, witty criticism is fun and maybe an important end in-and-of-itself. (Or: a culture of being able to talk about things normally considered taboo can be freeing and be valuable both for the insight and for the human need for freedom/agency). I've gotten value out of both of those sorts of cultures.

But if you're unable to challenge social reality without brusquely confronting it - or if that is the manner in which you usually do - I think there's a lot of net-truth you're leaving on the table.

There are people who don't feel safe sharing things when they fear brusque criticism. I think Robby Bensinger summarized the issue compactly: "My own experience is that 'sharp culture' makes it more OK to be open about certain things (e.g., anger, disgust, power disparities, disagreements), but less OK to be open about other things (e.g., weakness, pain, fear, loneliness, things that are true but not funny or provocative or badass)."

Brusque confrontation leads to people buckling down to defend their initial positions because they feel under attack. This can mean less truth gets uncovered and shared.

Collaboration vs Criticism For The Sake Of It

The job of the critic is much easier than the job of the builder.

I think that there's a deeper level productive discussion to be had when people have a shared sense that they are collaboratively building something, as opposed to a dynamic where "one person posts an idea, and then other people post criticisms that tear it down and hopefully the idea is strong enough to survive." Criticism is an important part of the building process, but I (personally) feel a palpable difference when criticized by someone who shows a clear interest in making sure that something good happens as a result of the conversation.

Help Brainstorm Solutions - If you think someone's goals are good but their approach is wrong, you can put some effort into coming with alternate approaches that you think are more likely to work. If you can't think of any ways to make it work (and it seems like it's better to do nothing than to try something that'll make a situation worse), maybe you can at least talk about some other approaches you considered but still feel inadequate.

Active Listening / Ideological Turning Tests - If you disagree with a person's goals, you can try to understand why they have those goals, and showcase to them that you at least get where they're coming from. In my experience people are more willing to listen when they feel they're being listened to.

Accompanying criticism with brainstorming and active listening acts as a costly signal, that helps create an atmosphere where it's a) worth putting in the effort to develop new ideas, and b) easier to realize (and admit) that you're wrong.

Truth As Impact

If you constantly water down your truth to make it palatable for the masses, you'll lose the spark that made that truth valuable. There are downsides to being constantly guarded, worried that a misstep could ruin you. Jeff Kaufman writes:

There are a lot of benefits to unguarded communication: you can move faster, you can open up your tentative thoughts to friendly consideration and criticism, you don't have the mental or process overhead of needing to get every statement as perfect as possible. You might say something that you don't mean to, but in a friendly environment you can correct yourself or accept someone else's correction.

Despite these benefits, it seems to me that things generally move in the more guarded direction, at least publicly, as they become more successful.

Daniel in the comments notes:

And I think one cost of guardedness that seems missing from the post is that guardedness can bias thinking in favor of more easily palatable and defensible ideas, both in discussions between people as well as one's own thoughts.

Unfortunately, I think it's a natural consequence of growing large and powerful enough to actually affect the big picture: If you're communicating, not to a few trusted friends but to the entire world, then a verbal misstep will not be something you can easily correct, and the cost may grow from "a few minutes of clarification" to "millions of dollars worth of value lost".

I'm not sure how to handle that paradox (Less Wrong is hardly the first group of people to note that PR-speak turns dull and lifeless as organizations grow larger and more established - it seems like an unsolved problem).

But there's a difference between watering things down for the masses and speaking guardedly... and learning to communicate in a way that uses other people's language, that starts from their starting point.

If you want your clear insights to matter anywhere outside a narrow cluster of contrarians, then at some point you need to figure out how to communicate them so that the rest of the world will listen. Friends who are less contrarian. Customers. Political bodies. The Board of Directors at the company you've taken public.

How to approach this depends on the situation. In some cases, there's a specific bit of information you want people to have, and if you can successfully communicate that bit then you're won. In other cases, the one bit doesn't doing anything in isolation - it only matters if you successfully get people to think clearly about a complex set of ideas.

Consider Reversing All Advice You Hear

One problem writing this is that there's a lot of people here, with different goals, methods and styles of communication. Some of them could probably use advice more like:

"Learn to criticize more kindly/constructively."
"Communicate more clearly."
"Keep in mind the layers of signals you're sending when you try to state 1st-order-true-things."

And some some could probably use advice more like:

"Make sure in your efforts to avoid conflict you don't gloss over important disagreements."
"Don't get so wrapped up in what other people think that you lose the ability to think clearly for yourself."

I started writing this post four months ago, as part of the Hufflepuff Sequence. Since then, I've become much less certain about which elements here are most important to emphasize, and what the risks are of communicating half-baked versions of each of those ideas to different sorts of people.

But I do still believe that the end-goal for a "true" truth-oriented conversation will need to bear all these elements in mind, one way or another.