It It Time to Move on from Anti-Woke? The Grand Finale!

Naomi and I close out our three round dialogue on whether it's time to stop indulging our anti-woke tendencies.

This is the last of the three installments of my dialogue with

Naomi Kanakia

(here are parts one and two).

I’d love to do a “letters to the editor” follow-up post, if possible, so please email me by, say, Tuesday, if you have something on the topic you want me to share. -Dan

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Naomi,

That was a fascinating short essay on race, liberalism, Janine, and the university. I want to address your arguments, some of which I find persuasive, but I feel the need to say something more personal, first, about how I make decisions about what to write about and whom to interview on my podcast.

I am a profoundly selfish writer and podcaster. I’m far less interested in achieving the right stance, or advancing the right political or moral outcomes, than I am in making art that feels authentic to my voice and emotionally satisfying to create. When I look at the feed of my posts over the past two years, since I launched Eminent Americans, roughly every fifth or sixth post/podcast ends up involving a critique of wokeness in some form. It’s a part of my brand, in other words, but not nearly all of it. I’m also fascinated by fashion, social class, conservatism, the history of the left, the psychology of writing, Jews, academia, television, masculinity, religion, sexuality, and psychotherapy.

Even when I’m going anti-woke, I’m doing so not primarily because I want to advance a perspective but because I desire generative conversation and engagement. I get bored very easily, and I hate the prospect of being boring to others. So I’m driven to talk to people, on my podcast, who have interesting brains and who say interesting things on topics I find interesting. Wokeness and anti-wokeness have been fertile territory for the last few years, and the people I’ve had on my podcast have been interesting on the topic, so in many cases that’s where I’ve gone.

You, for instance, have an incredibly interesting brain. That’s why I invited you on my podcast in the first place, way back when, in part to discuss these subjects. It seems to me that whenever you’re confronted with a complex question, you’re compelled to do a lot of hard and creative thinking to answer it to your satisfaction. I don’t know what to expect from you, in the best way, and I trust that wherever it is you land, it will be the product of genuine curiosity and lively intelligence. As we’re conducting this very dialogue, I look forward to reading what you say next. As

Adam Fleming Petty

said in the comments to a previous post, vis a vis Janine, “Leave it to Naomi to write a mini morality tale in her response!” Precisely.

Bill Deresiewicz has a different perspective than yours on some of these issues, but his intellect is alive in the way yours is. When I ask him a question, or put forward some thoughts of my own, he’s not querying his database of pre-formulated ideas in order to respond. I’ve interviewed those kinds of pre-fab people before, and it’s so depressing. Bill is thinking in the moment, playing off me, collaborating in an effort to push the conversation deeper. That’s what I love. I keep having

Blake Smith

on the podcast because he has such a fertile, hilarious brain, and he is so good at talking off the cuff. I did two episodes recently on preppy clothing and culture because I thought I’d enjoy the conversations, which I did. I suggested this back-and-forth with you because we were having an interesting private conversation and it felt generative to me. I trust my intuition in that way.

When I try to answer this larger question we’re addressing, of what we should be writing and talking about, I start here. Who’s interesting? Where’s the juice? And how do I cultivate my own practice so that I’m in proper relation to the juice?

I’ve spent a lot of time thinking and writing about the aesthetic fates of intellectuals of the past, the various ways they go right and wrong, and the conditions that are more or less conducive to good intellectual work. What seems clear to me is that the people who remain vital over a sustained period of time tend to be those who are flexible, introspective, open to critique from others, and curious about new evidence that complicates their premises. They are fiercely protective of their independence, careful about not getting sucked into ideological cul-de-sacs, and usually inclined to a certain self-protective distance when it comes to issuing or responding to the hottest of hot takes. So when I’m writing about Ta-Nehisi Coates, for instance, part of what I’m doing can fairly be characterized as anti-woke, but the bigger part of it is charting the trajectory of a brilliant talent who has been waylaid by ideology. Wesley Yang, on the other hand, has been waylaid by anti-woke ideology. That’s super interesting to me too. My recent conversation with Geoff Shullenberger was about the arc of “post-left” writers, tweeters, and podcasters whose antipathy to the left, and their capitulation to it, has landed them in a very dark and intellectually shallow right wing place.

A lot of what I’m doing I see as one step removed from woke or anti-woke. It’s interested in the conditions that produce these tendencies and the various responses that artists and intellectuals have to them. I am fascinated by the damage that wokeness has been doing to people. I’m interested in the damage that anti-wokeness is doing. I’m interested in people who are dumber or less interesting than they need to be because they’re trying too hard to avoid either of these poles.

There’s also a big part of my approach that is self-protective. I want to avoid personally becoming stupid and boring myself. As do you, right? You mention above your refusal to step into the role of being an anti-woke critic of your own people—the Brianna Wu role—and while I know you avoid that lane because you think it’s dishonorable, I assume you also avoid it because you fear it poses a risk to your talent.

We started this conversation with your question to me: “Your show spends a lot of time discussing woke people. Do you ever think...maybe you should have a woke person on?”

My slightly qualified answer is no, because I don’t find what most woke people are saying particularly interesting, nor do I have much confidence in my own capacity to be interesting in conversation with them.

It’s not impossible for me to land in the right conversational space with guests who have traditional left-wing views on topics like race, gender, sexuality, etc. My recent conversation with Carol Gilligan, on gender roles and relationships, probably falls into this category, as does my conversation on race and sports with Kiese Laymon and Jason Sokol. I had a good conversation with Corey Robin about the years when his Facebook page was a vital forum for discussion among left wing intellectuals.

I can do it well when the conditions and the guests are right—Gilligan, Laymon, Sokol, and Robin are all really interesting thinkers, and I was careful to come at the topics from a relatively oblique angle—but it’s hard to achieve those conditions and hard to find those guests. The left has been pretty boring for a while, particularly the woke left. It’s a lot of people saying versions of the same things the left has been saying for decades, often with little awareness of, or interest in, the ways in which aspects of the world should have complicated or refuted the old orthodoxies. So that’s a baseline problem. The quality of my podcast is also very dependent, I’ve come to believe, on the emotional connection I can establish with my guests, and that connection is very dependent on an implicit presumption of good faith. This ease in turn allows me to explore productive tensions between us. But with so many people on the further left I don’t share very many philosophical or existential premises, and we both probably bring a certain amount of suspicion or at least caution to the encounter. That can make it harder as a host to find the points of productive tension without undermining the emotional connection.

So it’s possible, but I’ll have to work harder to find the people whose left wing views are deep and rich even if I find some of their premises stale. I’ll have to do more prep to understand their perspective in advance, and to be able to draw out the parts of it that most reward close attention. And the conversation will almost always be more emotionally draining for me, because there won’t be as much trust. I’ll have to be much more conscious of how I frame my questions, insert my critiques, and articulate my confusions. All of this is worth doing, of course, but the necessary investment is higher, and it mostly hasn’t been worth paying, to this point, when there’s been such a deep bench of not-lefters with whom I’m so likely to have a rich conversation.

I agree with you, though, that something has shifted recently. The anti-woke critique is feeling more stale. The deep pathologies of the right are mattering more. The left is reckoning, in a more substantive way, with the failures of its critiques, or at least with the political inefficacy of its critiques. A whole set of new issues and challenges are on the table. The juice is loose.

So I don’t disagree with you, exactly, that many of the questions you raise are ones we should be addressing, but I’m not sure that we end up in the same place in our instincts about how and with whom to address them. I don’t want to talk to Janine; she sounds boringly unreflective about her beliefs and likely to be rigid in their defense. I don’t want to talk to Ibram Kendi. The best you can probably do with someone like him is emulate how Ezra Klein handled him in his 2021 interview; he gently but firmly identified points of tension or contradiction in Kendi’s thinking and then patiently listened as Kendi spun out what were clearly deflections and evasions. It was illuminating, in a way, but I can’t imagine it was very satisfying for Klein, and I don’t think it would have been interesting to listeners were it not for the fact of Kendi’s immense influence.

Where I’d want to go, instead, is back to the most basic questions about race, gender, sexuality, inequality, war, and justice that have animated the left for so long, perhaps the most fundamental of which I think you accurately identify as “the persistence of racial disparities even after many years of an ostensibly colorblind legal regime.” It’s the failure of American society to achieve some form of economic racial equality in the aftermath of the end of Jim Crow and the eradication of overt racism and discrimination from the major American institutions. This is the primal wound, I think, in response to which so many dysfunctional movements and ideas have manifested on both the left and the right over the past 60 years. There’s so much anger, shame, resentment, hypocrisy, embarrassment, denial, displacement, projection, and exploitation swirling around these issues. They fuck people up good.

I want to talk about the wound, because it’s fascinating and important, but not with genuinely woke people, or CRT advocates, because I think their strategies are failed, dysfunctional strategies for remedying the wound. I agree with you that these people are not evil, and that many of them are motivated by genuine desires for justice and healing. They’re on our side, in an existential sense, in a way that many on the right simply aren’t. But they’ve attached themselves to bad ideas and destructive movements, and so I’m hesitant to engage them because I don’t think the ROI would be great.

As for the white supremacists, race realists, race baiting talk show hosts, and MAGA politicians who’ve attached themselves to far less forgivable dysfunctional right wing strategies that have evolved in response to persistent racial inequality, I don’t want to talk to these people either. I’ll read about them, and occasionally write about them, but they’re not good conversation partners. Ross Douthat has been talking to some of these MAGA folks on his New York Times podcast, and I suppose it’s a valuable service to listeners, hearing how shallow and unreflective these people are, but it’s not great audio. I don’t want to listen to these fools spin their foolish theories.

These are broken people, who have no insight into why they do what they do. They don’t have deeper insight into the problem. On the left and the right, so many of the most visible actors make insight into the problem harder to develop, because their stale, bad, and rigidly held ideas crowd out the space where open and vulnerable conversation should be happening. I’m not saying there’s an equivalence between left and right, in terms of the risks they pose to our political freedoms (particularly yours, as a trans person). There isn’t. But they’re uninteresting in similar ways.

I want to talk to people who can be interesting with me. And who’s that? It’s not necessarily anti-woke people, or “not left” people, but it seems almost by definition it’s going to be people who’ve opted out of the conventional wisdom and pre-fab formulas on these topics. Early in my podcast I did an episode with Tim Lensmire, professor of education at the University of Minnesota and co-founder of the Midwest Critical Whiteness Collective. Tim is the author of a brilliant short ethnography on white people and race, White Folks, which I wrote about many years ago for The Point. Tim’s whole professional and intellectual identity is oriented around anti-racism; it’s his life passion to reduce the harm that racism does in America. He thinks, however, that much of the mainstream approach to anti-racist pedagogy is counter-productive. He wants us to do a much better job of combating racism in white people. Is that anti-woke? We certainly talked a lot about the conceptual and practical failures of left wing anti-racist pedagogy, but that’s because the left holds a total monopoly on anti-racist pedagogy. Who else is there to critique, when your motive is to improve the field? And we did it in the context of a shared understanding about how fucked up so many white people are about race, how important it is to ameliorate that, and how awful the right wing approach to race and racism in America is. The whole conversation is motivated by our shared conviction that American politics and culture are profoundly influenced by our history of racist oppression, but it’s not a conversation with a default woke person. Tim is very much not Janine.

I just requested a review copy of Total Market American: Race, Data, and Advertising, forthcoming in the fall from a young academic at the University of Illinois, Chicago. I assume she’s pretty left-wing, and I probably don’t love her solutions for how to fix racial inequality in America, but I’m utterly fascinated by how brands market to racial and other demographic groups, and I’ve been wanting to do something on that topic for years. It appeals to me in much the way that talking to Maggie Bullock about J. Crew and its complex racial symbolism appealed to me. She has expertise on a topic that fascinates me, and I imagine we can have a great discussion about how companies target specific demographics even if we don’t agree on how to attack larger issues around racism in America. I hope she agrees to talk to me.

For that matter, I want to talk to you. I mean, I am talking to you. I think you’ve been more vital and interesting on race in this very dialogue than 99% of the stuff out there. I think you have much more to say about Janine, and her world, than Janine would about herself, which is why I’d rather talk to you about Janine than talk to Janine. But then once again I’m talking to an eccentric, hard to classify, somewhat anti-woke person–you! Is that wrong?

Dan

—

Hi Dan,

I hear what you're saying. If I was you, I also wouldn't want Janine on my podcast. It wouldn't necessarily be a great talk, both because she'd be on the defensive and because you don't have respect for her ideas. You don't want to give her your time and attention for a show that you're producing for fun, basically.

And I hear that you want to make an effort to have more left-wing voices on the show. I think that's great. I understand that it's difficult, because the easy rapport that you have with heterodox voices isn't necessarily there.

But maybe that rapport is, in part, the problem. Maybe that rapport gives some of these heterodox voices too much of a pass. And maybe left-wingers sense that they'd get pushed harder, by you, than you'd push a right-winger.

What I'm hearing from this dialogue is that you perceive woke ideas as still dominating the culture sphere. Which means you have to engage with them somehow. But if you think it's part of your core mission to challenge woke ideas that've destroyed peoples' brains, and you don't want to have woke people on your show, then that's basically a commitment to continuing to produce anti-woke content in some form--I know that's not all you do, but it is a significant part of it.

And I really question the degree to which a person can retain their integrity if they put forth anti-woke perspectives without acknowledging that this perspective is...you know...it's the official ideology of the government of the United States! That serious state power is currently being waged against Janine. Her ideas are being persecuted by the government.

That's the context under which I, personally, view all anti-woke content these days.

And yet, where does that leave us? If we want to address these ideas, but we don't want to support them, and we also don't want to pile on and attack them, then what is there left to do?

That's why I proposed taking these ideas seriously.

I do think woke ideas will come back. We have not heard the last of them. A lot of my friends are socialist, and they hope some kind of class-first socialism will arise from this moment. But...socialism does not have good answers for the problem of racial disparities. A socialism that isn't race-conscious will just end up enriching poor white people at the expense of non-whites. That's one reason we don't have socialism--it's because poor non-white people don't trust it, they don't trust these promises. That's why they didn't vote for Bernie, and that's why he wouldn't have won the election even if he'd gotten the nomination.

These disparities will persist, in part because it's so often clear that race-blind regimes do encode a lot of racism. For instance right now we are seeing that this attack on DEI is, in part, an attack on the Black middle class. That some Black people managed to get good incomes working for the government, and now they're the enemy. Increasingly, even the presence of Black people is being viewed with suspicion. In California affirmative action in higher education has been illegal for thirty years, and yet California schools are being sued merely because the percentage of Black students has gone up over time. Thus we are entering a regime where any time Black people rise, it's presumptively held to be a result of illegal discrimination against white people. That's what being against "DEI" looks like in practice, I certainly have much more sympathy for woke ideas right now than I did two years ago, and that sympathy will only increase.

From your perspective, it's all about booking podcast guests. You pay a lot more attention to the thinkers and doers of the present day that I do. All these people you mentioned (Lensmire, etc), I had never even heard of them. I mean I only know about John Pistelli because he was on your podcast! Same with Blake Smith and Ross Barkan! These guys meant nothing to me, before I encountered them on your podcast.

And in fact I'm pretty sure your podcast is why I'm on Substack at all. I literally listened to it and thought, "Oh those guys sound okay, and they're definitely not transphobes, so maybe I'll move here." Best decision I ever made! All due to you, honestly. That's not smoke. You saying some non-transphobic stuff on a podcast two years ago made me feel safer coming to this platform that people said was extremely transphobic, but I honestly have not found that to be the case. I have no problem trans-washing Substack--it's not all transphobes here.

You know how to find talented, intriguing people, that's your thing. That talent doesn't work on woke people. They don't make your antennae go off. I understand that.

I am confident that the next big thinker about race or what-have-you, I'm sure I'll encounter them on your podcast.

That being said, I do think the current moment necessitates a somewhat-more-combative attitude towards some of your guests. Like, I do think your antennae may have become calibrated to a certain kind of dissident thought whose intellectual dishonesty is rapidly being revealed by the rise of Trump.

And it might make sense to take a minute to look around and recalibrate. Because I think that people who in 2025 are still genuinely worked up about wokeness and call themselves thinkers should understand that...whatever work they do from now on is probably not going to be good. For the sake of their own creativity, they have to acknowledge that they have won. That whatever it is possible for an idea to do when it's won, short of actually liquidating its opponents, they have gotten it.

And if they really are not prepared, at this moment, to defend Janine's right to free expression, then their own commitment to free inquiry is revealed to be false. They were never in favor of open debate and open expression of ideas--they were just unhappy that they personally weren't on top.

It seems now we have this two-step where people, yourself included, simultaneously say woke ideas predominate in the cultural sphere and that these ideas are so clearly unconvincing that they're not even worth debating. The natural corollary of this belief is that the cultural sphere must be eliminated. You can't have it both ways. You can't argue that the cultural sphere is important, and that it's dominated by people with self-evidently false beliefs who are impenetrable to logic.

If those things are true, then the only way to recover the cultural sphere is to bring it into line by force. And that is exactly what Trump intends to do.

And if that's what thinkers want, then they should say so. But if we let them go on a podcast and say a bunch of vague stuff without teasing out the natural implications of their beliefs, then we give them a pass. We allow them to keep their hands clean and avoid admitting what they truly stand for.

That's why if you have someone on your podcast, maybe it's worth challenging them, for their own good, just the way I've challenged you. Because I will be honest, there is a term for what I heard on your and Bill D.’s podcast, and that term is coordination. Bill D. feels this marvelous energy on the right, and he’s trying to see which parts of that energy he can agree with, because he wants to be a part of it. And as a result, he’s willing to give up his long-held beliefs, just because they’ve become somehow uncool, exhausted, unpopular.

This whole podcast is just giving preemptive permission to left-wing people to avoid fighting for what they believe in. He’s given up on improving the world, but feels embarrassed to say so openly.

And this lack of courage goes even further. He’s no longer even willing to state his own beliefs openly. Even the concept of free debate over controversial ideas is passe. For instance, at some point, in his podcast with you, Bill D. says, "I've come to question the wisdom of a lot of liberal policies." And you push him, you say, "Like what...be specific..." And he doesn't really answer. He hems and haws. Just a lot of liberal policies. He says it was a big moment, a big turning point for him, in 2020, when he really started to change his thoughts, but...he won't say exactly what thoughts changed. Instead he just says: "...cause, you know, center right economists, like, well, whatever your goals are, is this really the best way of going about it?"

Daniel, he is talking about race.

He pivots to a discussion about how you don't need to go to the Ivy League to lead a respectable life. He's saying Black people don't really merit being represented in the Ivy Leagues. I know it, and you know it. That's what it means when he says, "This all comes from listening to Glenn". Glenn Loury is a Black economist who is against affirmative action. That's what Bill D. is saying. And you know it, but you don't call him on it. It's a subtext that most listeners to this podcast understand--a subtext that underlies most of the anti-woke sphere--but it's something anti-woke people have never really had to grapple with, because they haven't been in power.

This is the anti-woke worldview. This is anti-woke politics. It’s a bunch of people listening to podcasts where they imbibe controversial ideas. Then they reassure themselves that they are so brave for considering those ideas in the privacy of their own minds, and meanwhile they say nothing while a would-be dictator breaks the law in order to forcibly enact those controversial ideas, all without the anti-woke crowd ever needing to admit, either to themselves or to others, the degree to which they support what’s going on!

The enervation and spiritual bankruptcy that Bill describes is his own enervation, his own inability to call out the evils that he sees. He has the ability to speak directly to an audience that would listen. He has the ability to say, "Enough is enough. We won. Let's move on." But because he doesn't have the energy to say that, he externalizes this problem, saying, oh, the left doesn't have energy. Bullshit. He is the one who's lost his energy. Because he himself has lost faith in liberalism. He himself has lost faith in free debate and intellectual discussion.

Moreover, he resents the left-wing’s insistence on talking about right and wrong. He wants to be freed from those notions, just wants to be free to play and express his eros, his life-force et cetera. It’s not just the left-wing’s specific ideas that he objects to, but even the very notion that we should care about justice. It’s too tedious to worry about justice. Let’s just worship strength itself. But…that is fascism. That is the essence of fascism. I understand that fascism has an appeal. I feel it myself: it’s very impressive what Trump has done. I also had resentment towards cultural elites, and part of me also feels glee at how they’ve been attacked. But that is an ugly feeling, and it’s not a part of myself that should be given free reign. Maybe Bill’s essay in Salmagundi has more nuance than what I heard on the podcast, but what I heard there was very dark indeed, and that darkness is what prompted me to reach out to you in the first place.

—

Finally, you might ask, "What do you believe, Naomi? What is your vision for the future?"

Personally, I admire Gandhi. And Gandhi did not worry about strength. He worried about commitment. He was committed to principles he thought were right. And he thought the rightness of his principles would give him the spiritual force, the satyagraha, that he needed to overcome his enemies. He felt that so long as one person remained who was committed to the truth, then he would inevitably win, because truth has more intrinsic power than untruth.

Is there truth in what the right is saying? If so, to what extent? That should be the role of an intellectual in 2025. We don’t need handicapping. We don’t need to be told they have big ideas. We know that. But are those ideas true? Bill D. refuses to say. Because he knows the answer is that they are not. And I will go further and say that woke ideas have much more truth, in the end, than the ideas put forward by the anti-woke coalition.

But democracy and rule of law are also ideas that have considerable truth. And if a policy is enacted by law, then that's fair enough. California banned affirmative action through legal processes. I don't agree, but I think that's fair enough. Woke tactics, particularly their intolerance for dissent, was genuinely unpopular and engendered a backlash. Private universities are subject to pressure by their donors, students, and other stakeholders, and if they want to stop funding some form of expression, that's also fine. Public universities are more directly subject to the people's control, and if they want to stop funding certain kinds of programs or teaching certain classes, that is also their right.

I personally see a lot of value in woke ideas. I don't reject them as categorically as you or Bill D. But it's understandable if the people don't want to fund self-critique. What is happening right now goes way beyond that however. The government is targeting specific institutions and bringing them to heel as a pure expression of power. The government is telling law firms who they can and can't represent. The government is telling private universities to ban certain forms of speech. In Penn's case, because they had one trans swimmer three years ago, their existence as an institution is in danger. The clear intent is to make institutions afraid to accommodate trans students. That's not only illegal, it's immoral. And it shows a deep level of intellectual bankruptcy on the anti-woke side. They cannot win through legal means, so they'll attempt to win by fiat instead.

And if woke ideas persist (as you have insisted that they do) even after all this oppression, then think about what that reveals. It shows that actually these ideas have power after all. That they do in fact have a life-giving power--a power that is revealed by the fact that they quite literally have given people the strength to resist the full force of government oppression. And anti-woke ideas will, in turn, have been revealed to be animated by nothing more than petulance and hatred and grievance.

And it is in this clash of forces that the true life-giving power--the eros--of the left will be revealed. Because hatred and grievance do have power, yes, but that power is not generative power. Wokeness, for all its faults, was organized around genuine societal issues–racial disparities in wealth, income, and criminal justice–that we all know are unacceptable, unjust, and unsustainable. This right-wing movement is founded in an avoidance of that truth. And yes, people are expending a lot of psychological energy attempting to escape from what they know, but eventually they will exhaust themselves with that effort, and the truth will win out.