The other aspect to consider is that to have deep conversations, you essentially need 95% reading 5% actual discussing because the depth can be pretty high on most topics.
To give a practical example: you can have a deep and touchy convo about the place of religion in life, but in all likelihood every argument you will come up with will have already been written about in far more depth elsewhere. By the very nature of the medium and its history you are only going to have the illusion of depth if you only seek to have conversations as you are describing.
It would also be a good idea to carefully consider what you consider touchy. Chances are, it's just normal things to think about for your demographic. For instance, HN readers like to talk about controlling the masses, large future trends, and revel in the forbidden aspect of discussing this sort of thing. But in reality, population control and an 'architect' view of their place in the world has been a normal feature of the well-to-do classes for pretty much forever.
People like to look back with rose tinted glasses at the "good old days" of free expression online, but choose to forget that such conversations with strangers inevitably led to misunderstandings and bad faith assumptions, degenerating into smug superiority fests at best or flame wars at worst.
I post occasionally on HN because it's a lot better than other places I've posted to in the past (Usenet, Slashdot, Reddit etc), but even this is but a pale shadow of the conversations I have in person over drinks.
It's a far wider, more interesting range of discussions at one of those events than I've found on the internet, and I'm trying to figure out ways to have them more frequently as opposed to the once or twice a month that's been standard for the past few years in my social circles.
There are some shadows of that in some Signal groups and Matrix rooms on private homeservers, but mostly those are spawning things to discuss next time we get together in person.
I don't know anyone who "posts a full range of their thoughts" online anymore, except in fairly well secured private encrypted chat locations, because of just how toxic the whole place has become.
It's a blog section on a non-English website about Linux, but the blogs are about anything - current events, niche engineering topics, etc. The discussions are threaded, with no comment voting. It seems like people there have much more distinct and varied personalities compared to HN or Reddit, where comments sometimes seem like written by a single person. The quality has degraded over time though.
Public discourse is a performance. Not that it is fake, but it is the refined product of practice you can't see unless you have practiced it yourself. When you go see an orchestra and wonder why you can't get up on stage and just jam with them, is it censorship, or is being a part of that performance the effect of something that takes a lot of effort to be welcome in? Start your own punk orchestra or get good enough to be welcome in an officially sanctioned one.
My conversations have been on signal groups, slack, pints with fraternal bros, meeting people while travelling and motorcycle camping, drinking at family bbqs, are typically with other men, and an less on boats these days. What they all have in common is they have a bar to entry of not being a sad sack. I agree that there are legitimately lame orchestra admission rules on official social media, but think about what being open, funny and welcome really means, and I guarantee you will get invited everywhere.
...that wasn't a answer. Here's an answer.
Although their flaws are numerous and well-documented, including their often distasteful beliefs, and although their communities have tons of structural ideological bias, you should check out the "rationalist" community. They can be found on various forums. The discussions on touchy issues have largely moved to forums that are smaller but still public, which can be found with a bit of effort.
One issue with them, and at least one other community I know of with a lot of the "learn it yourself" mentality, is their relationship with subject-matter expertise and authority. It's bloody exhausting to defend oneself against a bunch of ignoramuses in a debate in a tree-style forum, so there's a lot of weird crap ideas floating around. But, at least it's vaguely what you're looking for.
> late-night dinners with VCs or yacht rides with rich people
Wat? Where are you coming from?
> conversations that are deep about touchy issues
Everybody does this, all the time. Maybe your friends are too shallow for you?
> Where are the places to start (and continue) conversations about important issues without self-censoring and walking on eggshells?
Go ahead and have them, right here on Hacker News.
If you're "self-censoring and walking on eggshells" and you're NOT just an asshole, then you just need to study rhetoric. It's an ancient art, thousands of years old, there's plenty of material to work with.
If you're well-spoken (and your opinions or ideas are not simply odious) then who cares if people get mad at you? It's on them to reply in kind or they're the assholes, eh?
And there is everybody else. The vast majority. The "normies"
Everybody talks to everybody on the internet. Therefore every stranger is surrounded by normies.
At best the stranger is ignored. At worst he is shouted down.
This creates a ubiquitous field of strange idea suppression.
One must find a private club. That's hard.
There is a weird absence of private clubs on the internet. Or at least they are hard to find.
I guess any private club that advertises its existence immediately gets stuffed with normies.
A long, long time ago, I ran a BBS: now I run a Mattermost server. Feels like about the same level of quality to me. The conversations there run the gamut from lower (more vulgar, less mature) to higher (more in-depth, lengthier, more thoughtful, taking place over a longer time frame) than, say, Twitter, Reddit, or HN.
It's not hard to set up an invite-only, hosted chat server. It is somewhat harder to convince people to use it, because a lot of people don't want to run another app.
If I had to choose today, I would go with a Matrix-based solution rather than Mattermost, but it wasn't available at the time. Most solutions, including Mattermost, lock you in by not letting you export the (full, including DMs) conversation archive, so you have to choose something you want to stick with for a while.
Online discourse is certainly not safe anymore, so yes we do self censor, and because of that we get out of the habit of expressing raw thought or trying to challenge the status quo for fear of being reported or banned.
It's a real shame. The internet was supposed to be this great opportunity to unify people and help push through a new way of collaboration and debating, yet it's become an albatross around all our necks.
Without healthy debate with controversial or opposing opinions we are never exposed to any viewpoints that differ from our own, so we all just end up swimming in our own echo chamber fishbowls, and the field of intellectual thinking just dies.
I'd like to wax on further about this, but I'm typing (badly) on my phone which is in itself to blame for the brevity of online conversation.
But if you have an established friendship with someone, and have a baseline of trust and respect, then you can have those challenging discussions. But make sure you are really open to being wrong. Most people are not.
Interesting discussion between people who disagree about important issues never really existed online. As someone who has been online since the 80s, you can take my word. The internet is mostly good at matching up people who agree due to the effect I mentioned above.
I've been having these types of conversations with my brother nearly every day of the week for the past two decades.
There are no barriers to what we can discuss. No eggshells needed. He's a rational, intelligent person. I certainly wouldn't put our conversations on Twitter (or Reddit or xyz), who has time or care to deal with explaining to morons/irrational people/mentally ill people/partisans/whatever why their feelings/emotions/politics/opinions aren't the center of the universe - and who cares what strangers and anons think anyway in most circumstances; their opinions, their thoughts, their feedback, it's all overwhelmingly worthless.
I have a couple of friends I can do this with as well. They're out there, find them.
What are the touchy conversations on yacht rides with rich people - how to avoid the mistakes Jeffrey Epstein made with his private jet private island child sex trafficking operation?
Definitely a chicken and egg problem to attract users, but I've got some ideas in the works...
It's not the 'where' that matters, it's the 'who'. It's the people having the conversation. I've had meaningful conversations on Disqus more than once, which normally you would not think would be a place you could have such conversations.
Previously discussed here: https://news.ycombinator.com/item?id=31210680
In context of modern social media, the main stake is emotional involvement. Which is often a sign of a shallow understanding of a subject.
Take reddit conversations on controversial subjects. There would be loud statements with many upvotes and counterpoints with many downvotes. And downvotes discourage debating for regular people. So you are left with homogenous opinions and trolls.
I think interesting conversations may happen with individuals that you stumble upon by chance. Easiest way to get lucky is to be involved in some community that fits your interests.
edit: but on the other hand, it's quite easy to get in touch with famous and brilliant people if that's what you like, so... if you have something interesting to say, maybe you'll get somewhere that way.
Why? because there's many of them and each of them may attract different groups of people, thus different discussions groups, forums, etc.
I have a few questions:
1) What is an interesting conversation even? Seriously. In my experience there's endless 'interesting' conversation happening on the big site aggregates, even if you have to do a little work to do it. Most of it doesn't just happen to you though.
2) Was there ever a time when deep conversations were happening on the internet? Really, truly. I wouldn't consider stumbling on a thread and reading it unique to old internet.
3) Deep and touchy? You're going to have to define Deep. Because, pick your interest. The depth of information to be found and conversations to be had about... picking a random interest of mine - Visual Art. I can go on Youtube or Twitter and see any number of threads about: NFTs and their place in the wider space, same with AI Generated Art. I can find videos on technique that are deep and technical. There's any number of discord servers to join that if you engage in good faith, people will respond in kind. (One trick is to simply ignore folks who make 'derailing' comments. Here's a secret I thought everyone knew: Trolls and the ironic posters want attention, if you don't give it to them they simply go away; Their biggest fear is being boring, use that against them lol)
I'd be interested in what examples you have of 'self-censoring' and 'walking on eggshells'. Seriously. Even the most 'Touchy' subjects I can think of, take your pick of culture war nonsense, if you engage earnestly, deeply, intellectually, there's open discussion to be had.
But it seems you have to bring your own audience to Twitter. At least that is what I witness. Everyone who got a conversation going over there was a celebrity outside of Twitter already.
I have my suspicions, but I hate being that cynical…