How To Have Difficult Conversations

Hint: Not on Twitter!

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Last week, while on a long drive, I caught up on some old podcasts. I generally gravitate towards interview or conversation because they capture uncertainty and complexity much better than other forms of media. A good longform conversation allows for the explanation of partially baked ideas, and the back and forths are rarely definitive. Sometimes, you can hear the participants searching for the right language, or expressing ambivalence about an argument with which they mostly agree. Someone can still have terrible hot takes or come off like an asshole via audio, but there’s a bit more friction. It’s harder (albeit certainly not impossible) for people to take your earnest ideas in the worst possible faith when they can hear you talk them through.

One of the older podcast episodes I listened to last week was an episode of You’re Wrong About on the subject of Cancel Culture, which I thought did an exceptional job navigating a complex, treacherous topic without falling into worn rhetorical traps. What struck me listening to this episode — and why I felt compelled to newsletter on it, here — was how impoverished our language is around highly contentious or culture war-adjacent topics.

Often, with a term like “Cancel Culture,” there’s zero hope for a productive discussion because the loudest voices in a given space or on a platform are arguing about semantically different things. They’re using the same words, but they’re not abiding by similar definitions. Here’s how You’re Wrong About host Sarah Marshall described this human assimilation of information:

We will have a term like ‘cancel culture’, or ‘human trafficking’, or ‘hipster’ back in the day, and people will walk around with a fairly specific idea in their head of what that is. And then they'll encounter that word and they'll be like, ‘I know what that word means.’ And really that word means like at least 25 things. And it's just hard to clarify in a public conversation or like a breaking news item of some kind or another, what iteration of that word, are we using here? 

To drive the point home, Marshall’s co-host, Michael Hobbes, attempts not to use the phrase at all in their conversation:

“I think most of what we're actually talking about in the cancel culture panic is things that we already have terms for,” he says. “Like perfectly reasonable terms for like people being fired, or like people being criticized widely. I just think it's actually very easy to talk about all of the phenomena within cancel culture, all of the anxieties underneath it without actually using the term. And if it's that easy to talk about it without using the term, then what do we actually need the term for?”

Removing the buzzword actually frees the hosts to discuss specific examples of supposed incidents of cancel culture: from high school students getting “cancelled” by their friends for being creeps, and the various functions of and blowback to the #MeToo movement. Some recent instances of the term that they discuss end up being less about swarming mob justice and more about shitty media incentives that encourage coverage of low stakes internet drama. Marshall and Hobbes argue that a lot of what is deemed as Cancel Culture is, to a degree, a product of still-new online public square social media dynamics to which we’re all still struggling to adapt. Their discussion, in other words, is nuanced.

To that end, Marshall notes that Cancel Culture is, “a term that has been co-opted by the right, but also, I think to me it feels real.” She says that she is, in many instances, afraid of getting yelled at by tons of people online or of being ostracized for misspeaking in some way and suffering outsized consequences.

This might not sound groundbreaking, but I thought it was a crucial admission. Because when subjects like Cancel Culture enter the culture war fray, their vague, fuzzy meanings mean that many ‘warriors’ get pulled into declarations and defenses of false binaries. Debates devolve into shouting matches about whether the phenomenon at large is real or fake. But the truth is that public shaming and the conversation around it are based off of a whole host of conflicting anxieties around power, speech, public discourse, and in-group/out-group behaviors. None of us are immune to those feelings, which is part of why it’s so difficult to stop talking about it.

By embracing the complexity of the the term, You’re Wrong About is able to find more universal language to talk about the overarching concept of public shaming. I don’t think the hosts necessarily find common ground with, say, Fox News’ primetime lineup — but they also don’t come out the gate suggesting that the phenomenon is an apparition that appears only in the minds of CPAC attendees and Twitter-addled centrist pundits. And that, I think, is helpful. It’s a sort of rhetorical olive branch: we all have neuroses about being excluded in some way.

That posture is in sharp contrast to arguing over vague, blanket terminology — which, again, is what most online and on-air and even IRL discussions tend to do. Because “Cancel Culture” has become an animating issue for conservatives, progressives have, in turn, pushed back against their understanding. But, as Hobbes notes, the liberal embrace of the terminology can backfire. The more attention paid to the phenomenon, even to debunk disingenuous claims, reinforces the idea that Cancel Culture is an issue of concern. “I don't know how I feel about it,” Hobbes says about the buzzword. “I don't know if there's a way to talk about it on the left without reinforcing the fake version of it on the right.” The term itself becomes a linguistic, political trap.

Listening to this conversation in sequence helped clarify how incredibly difficult it is to have substantive, meaningful, and generative conversations on heavy topics with deep personal, political, cultural, and historical resonance. At one point while listening, I found myself feeling overwhelmed by the complexity of the language we use to make sense of our place in the world and to exclude others from it. For a moment, I felt a deep sense of despair — how is it even possible for us to have difficult conversations?

How does a show like You’re Wrong About pull it off? The show seems designed to propagate nuanced discussion. For starters, the two hosts happen to be friends. There’s a palpable feeling of safety that seems to structure their discussions. The hosts may challenge each other or disagree, but there is a sense of support and assumed good faith.

And then there’s the podcast form — in this case, intense yet informal. The episode is not the product of two people sitting down cold at a microphone and riffing off the cuff. In the beginning of the Cancel Culture episode, Hobbes tells Marshall that he has compiled 189 pages of notes while researching. The ensuing conversation has beats, based around historical examples. Despite the narrative architecture and extensive preparation, the hosts still have ample space to talk to each other, to, well, process, and digress. The episode isn’t a polemic. The conversation — the exploration — is the point, not the destination. Nobody needs to win the discussion.

Now, compare those elements of successful conversations to the structure of other forms of media where these conversations usually take place. There’s cable news, which is where millions of people consume their daily political conversations — a medium that thrives on shorter, shallower segments. Conversations are framed by chyrons and graphics with short snippets of text, reductive by design. Conflict makes for the best content.

Social media offers a weapons-grade version of this format (it also acts as raw material for cable news segments!). I’ve written at length here about how social media, but especially Twitter, collapses context to tragic effect. Conversations meant for a specific, supportive audience are broadcast to hostile audiences with the click of a ‘Quote Tweet’ button. On other platforms, content is pushed algorithmically to audiences who often lack meaningful context. The architecture of these spaces incentivizes off-the-cuff, unstructured conversations that are framed in the most sensational manner, in order to attract attention. Many social media platforms are essentially a service that makes conversation feel less safe. And we’ve agreed, purposefully or not, to port a great deal of our public conversations to these forums.

On these platforms, conversations take the opposite route of the You’re Wrong About episode. Instead of shedding vague, loaded definitions of terms like Cancel Culture in order to better talk about the real problems at their root, we end up yelling almost exclusively about the definitions. Of course, few of the participants in these ‘debates’ agree on a definition, so the conversation goes nowhere and only devolves. Each side becomes the one-dimensional caricature of the enemy and, as Hobbes argues, the conversation only “reinforces the fake version” of the other side’s argument. No side wins any converts or debunks the others’ claims. As I put it back in 2017, “Somehow, both sides are winning even if nobody feels like they are.”

Four years later, I think a better description is that both sides feel like they are simultaneously winning and losing. You feel more confident in your ideas and with your affiliations. You feel righteous dunking on jabronis online. But you also feel like dogshit because it’s a conversation without a genuine purpose. Nobody learned anything, nobody grew as a person. More importantly, such attempts at difficult conversations only raise the temperature on the subject, making it all but impossible to meaningfully discuss.

Perhaps our political conversation is too polluted by bad faith and alternate realities for any of this to matter. Even as I lament the lack of public spaces for people to have difficult, meaningful conversations, I’m not sure if we can bridge our divides. I don’t know what getting a MAGA election denier in a room with a hardline progressive would necessarily accomplish. I am not suggesting that there was some halcyon era of great debate to which we need to return.

But I do think think it’s important to understand the work that goes into debating and analyzing culture, politics, and history. And it is work. The internet and our myriad media ecosystems have expanded the breadth of conversations and the number of participants but have managed to flatten a lot of our language. In politics especially, we lean on buzzwords and fuzzy terminology as stand-ins for sprawling complex debates, and once those words — like, say, Cancel Culture — become big enough, we’re incentivized, especially in media to use them more often. They make for great headlines and good search engine optimization. I am guilty of this myself.

I want to believe technology and media could eventually help facilitate an unflattening of our political and cultural discourse. But I’m not sure difficult conversations can scale. And, even if they can scale, I don’t think we can have them while we also have algorithmically juiced platforms that flatten and collapse context and only ratchet up tensions. Just today, Twitter announced a new feature that will allow users to change who can reply to them after they’ve tweeted. The feature is a way for users to self-moderate their accounts in the event that one of their tweets get swept up in the context collapse I described above and becomes a vector for dogpiling harassment. Garbage Day’s Ryan Broderick called it, “The ‘...so, you've become today's main character’ killswitch.”

What Twitter is really doing is breaking itself a little bit to make people “feel safer” (those aren’t scare quotes, just Twitter’s own language). Back before it took harassment as seriously, the social network used to privilege frictionless conversations at scale. Effortless replying and context collapse were features, not bugs. One could argue this new feature is a tacit admission that Twitter, when it works as designed (maximum, frictionless engagement), results in the opposite of meaningful conversations. The ideal experience on the service (going viral) is actually unsafe. That’s worth thinking about across all media, beyond Twitter.

We need more spaces for digression and uncertainty and searching conversations. For thinking out loud. If they are to exist, these spaces will have to be smaller and what comes out of them will not be easily translatable into bite-sized content. They not be lucrative conduits for ads. I don’t know if any of it is possible and I’m not holding my breath, but I hope the people who are designing our digital future stop thinking in blunt terms of “connection and engagement” — and start thinking about what comes next.


Ok! That’s it for today. I’ll be back Thursday with a great Q&A on how we can grapple with the climate crisis in the media. And I’m currently compiling some fun timewasters and links for a subscriber-only post. If you have some recs, reply to this email with them!

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