Below is the full version of the essay I’ve been publishing to this point in installments, a choice that was intended to be brilliantly strategic but was, I recently learned, based on a fundamental misunderstanding of how writers like me optimally amass readership on Substack.
What I should have done instead, argues Naomi Kanakia in her recent essay “A guide to effort posting,” is give readers the full, very long thing all at once.
Naomi’s (very effortful) post is worth reading in full, but the gist is that she began to notice, after a while of Substacking, that it was her super long posts that tended to gain her a disproportionate amount of traffic and new subscribers. She writes:
Effort-posts are often four or five times the length of a regular post. Yet they’re seemingly read by many more people than a regular post. So what is going on? How can this be possible?
The answer, I think, is that an effort-post is not necessarily read by a greater percentage of people who receive it, but that the people who finish an effort-post tend to like it much more. If they make it to the end, they usually feel impressed and pleased, and they’re much more likely to share your post. This means your post gets distributed widely, landing in front of more eyeballs (which ultimately means more readers).
I had imagined that by slicing my long essay into five or six installments, I was simply giving it more chances to hit. What I was doing instead was giving people a bunch of what Naomi calls “Regular Blog Posts,” or RBPs, which are perfectly fine on their own terms but don’t seem to generate the same sense of investment and desire to share that the super long posts do. Each of five typical RBPs, in other words, packs much less than a fifth of the viral potential of one effort post of the same total word count.
Effort posting isn’t remotely a sure bet. It has to be interesting. You have to get lucky. Etc. If all you care about is traffic and subscribers, there are more efficient strategies to acquire them. But if you’re already writing long, as I was in this case, and you have a readership that is open to reading long pieces, one long post is a better bet than multiple RBPs.
Lesson learned. I fear that I’ve already diffused too much potential viral energy through my misguided slice-and-dice approach to take advantage, at this point, of the typical effort post potential, but I’m going to go for it anyway. Here’s the whole thing, which includes what would have been the final installment at the end as well as a bunch of new footnotes that are mostly smart comments I got from various people on the individual posts.
Read it. Feel impressed and pleased with yourself for getting to the end of it. Have a desire, therefore, to do something with the effort you’ve put into reading it. Prove Naomi right. -Dan :)
The Failure To Be Interesting
About halfway through Marc Maron’s recent interview with Barack Obama, the final episode in Maron’s extraordinary 16 year run as a podcaster, I realized I was zoning out. The goal of having Obama close things out, for Maron, was clearly to make the end of his podcasting journey feel profound and emotional, and I certainly got the logic. Obama had been on the show once before, in the waning months of his presidency, and it had felt special. Maron wanted to evoke that feeling again, but this time Obama was speaking in platitudes, on topics where he either lacked deep expertise or hadn’t been meaningfully challenged in years. And he wasn’t giving himself to the encounter in the way that he had the previous time.1
It was a striking example of a fairly obvious but undertheorized truth: accomplished, influential, and highly respected people are often quite boring in public. It can and routinely does happen even to people, like Obama, who’ve been captivating in public before.
As a writer, interviewer, and communications professional for the last few decades, I’ve amassed a great deal of experience in this realm. I’ve written a lot of speeches for people in leadership. I’ve interviewed a lot of people, including a fair number of rather fancy people. I’ve listened and read, with a critical ear and eye, to hundreds of interviews with high profile, high status people. I’ve endeavored in my own writing and speaking to be interesting. Along the way I’ve formed some hypotheses about the types of psychological and structural errors that high status people make when they fail to be interesting in public. I’ve also developed some fairly tentative thoughts about strategies that might help them avoid these errors.2
This essay is an attempt to map the terrain of public dullness among the potentially fascinating. It’s also, if I’m being candid, a test to see if I can be interesting in a way I’ve never tried to be interesting before, as a writer of self-help literature. Can I pull it off, or will I prove to be just as boring as the people who are implicated by this critique?
Finally I want to make a case, by the end, that understanding why we fail to be interesting in public can be valuable not just for those of us who aspire to succeed in some fashion as a public voice, but for all of us when we’ve reached an age, and a degree of maturity, where we possess wisdom and insight that we’d like to share with others.
THE FIVE RISKS
1. Internalized Politics: The Cost of Caution
There’s an obvious way in which internalized politics are the enemy of interestingness, and a more subtle way. Both are worth articulating.
The obvious point is that if you have a lot of real and imagined constituencies you don’t want to offend or disappoint, you’re almost certainly going to be too cautious to be interesting.
High status figures tend to operate within incentive structures that reward caution and punish spontaneity. Politicians are trained to avoid offense, pander to constituents, stay on message, and answer the questions they wish they were asked. CEOs have a fiduciary responsibility to consider the interests of employees, board members, and shareholders when they’re speaking in public fora. Celebrities (and their people) obsessively curate their celebrity brand, wary of alienating directors, producers, studio executives, media gatekeepers, and fans.
The best interviewers know this, and in particular don’t like to interview politicians, who are the worst offenders in this space. When heavy hitters like Terry Gross or Ezra Klein make exceptions, it’s often because the politician is someone who has distinguished herself from other politicians by being more outspoken, more willing to risk offense. Even then, however, these interviews are rarely the most interesting ones they do. “Maverick” politicians are still politicians, which means they’re walking a much finer line than one wants to be walking when trying to be interesting.
The more subtle way in which internalized politics present a risk to us, in our endeavor to be interesting in public, is that over time the logic of caution begins to shape not just how we speak, but what and how we think. The politics cease to be merely a filter we layer on top of what we’d like to say, but instead are fully internalized, naturalized. The risk-averse posture becomes so habitual, so baked into our professional and social interactions, that we stop even entertaining the kinds of thoughts that would need to be censored in the first place.
Many of us enter into our professional lives with a kind of double consciousness. There’s what we say, to survive and advance within professional structures, and then there’s the internal critical commentary that accompanies it, the voice in our head that knows when we’re spouting bullshit, when we’re holding our tongue when someone else is, when we’re going along to get along. It’s hard to keep this critical voice alive, though, within an ecosystem that pervasively disincentives it. The costs are too high. It introduces a hitch into your capacity to communicate the company line or affirm others who are doing so, which renders you less likely to advance within the organization. Also, it’s simply draining to question yourself all the time; there’s an energetic cost. Much easier to just silence the second voice.
The gradual result is that in so many environments—politics, corporate leadership, academia, media—the incentives and disincentives begin to shape the contours of curiosity itself. We learn to ask only the questions that are safe to answer. We develop intellectual habits that steer us away from ambiguity, contradiction, unorthodoxy, or anything that might produce distress in others or ourselves. We become careful not just in speech, but in thought. The mask becomes the face.
The result is predictability, caution, smoothness—enemies of interestingness.
What audiences crave is surprise, novelty, authenticity, emotional activation, and truth. But each of these, and especially more than one of them in combination, tend to come into existence as a result of an exploratory and iterative process that inherently involves risk. It requires saying something that hasn’t been pre-cleared by a legal team or marketing group. It requires a willingness to be wrong, to be misunderstood, to be vulnerable. It even requires a willingness to be awkwardly and embarrassingly boring in the short term, when you’re piloting your message, working out its kinks, evolving toward its strengths. Safer instead to deploy the kind of smooth and competent B+ boringness that most of us have mastered by the time we reach adulthood. This risks neither genuine interest nor genuine embarrassment, and is entirely sufficient to advance through most professional hierarchies.
Very few professions incentivize being interesting over being careful, and the cost in this realm is clear. If too much of your cognitive bandwidth is devoted to avoiding mistakes, there’s not enough left to say something true, or strange, or illuminating.
The irony is that many of the very people whose lives are in one sense the most interesting—those who’ve mastered complex organizations, built impressive things, made consequential decisions, witnessed history firsthand—are often the least able to speak about those experiences in a way that feels alive. Their caution, however justified it was when they were building their careers and profiles, becomes a kind of rhetorical and cognitive self-sabotage that almost always persists beyond the point where they need the caution or protection anymore. Barack Obama didn’t really have anything to lose by taking some risks on Marc Maron in 2025, but he was so accustomed to having something to lose, over so many years, that the interestingness muscles had atrophied. He could probably get them back in shape, if the stakes were high enough, but he would need to get back to the gym.
2. Deference: The Feedback Vacuum Around Power
By the time highly successful people feel motivated to step out as public figures—writing books, giving interviews, delivering keynotes—the incentive structure that surrounds them is rarely optimized for honest feedback. Their colleagues, subordinates, and collaborators admire them, depend on them, or simply fear the consequences of being candid with them. Which of their direct reports is going to say to them, after a high-profile discussion panel, Ted talk, or podcast appearance, “It was fine, but not very interesting”?
This is the problem of deference. We all know that honest feedback is essential to improvement, and that deference short-circuits that process. It creates the illusion that one’s existing skills are easily transferable. It encourages the belief that being good at one thing—running a company, winning elections, publishing research—means you’ll be good at talking or writing about it in public. But the truth is, most people aren’t. Not at first. And because they’re surrounded by people who won’t tell them otherwise, they may never realize it.
This is one reason why even the assistance of experts in communication—speechwriters, ghost writers, comms professionals like me—tends not to solve the problem. The technical polish can be bought, by hiring a skilled technician, but the power dynamic isn’t usually conducive to interestingness. The collaborator may be competent, but they’re deferential. They won’t push back, won’t challenge the speaker to be more candid, more specific, more human. And without that push, the final product is often lifeless.
The paucity of honest feedback is a problem for almost all of us, once we leave the very specific institutions—school, apprenticeships, training programs—that are specifically optimized to that purpose. When we’re young and inexperienced, however, we face a world painfully full of structures that let us know we’ve failed, if not always why. We don’t get jobs, promotions, dates, opportunities, awards, even as we watch some of our peers move past us in various ways. So it’s clear to us when we’ve come up short, and we tend to be quite motivated to figure out how to do better in the future, in order to avoid further failure and facilitate advancement. We’re incentivized to remain open to the data of the world, in many cases to seek it out.
At some point, though, if we succeed enough, the balance tips. The data of the world ceases to be so intrusive, and most of us cease to be as driven to receive it. We get fewer rejections. Success leads to more success. Expertise accumulates. We grow more confident. We mentor others, rather than being mentored ourselves. There are fewer and fewer people around us who are motivated and empowered enough to give us constructive feedback on our performance. We also just get older, and more settled, and further along the arc of our lives. The drive to succeed attenuates. This isn’t a bad shift. In most respects, it’s a good one. But it can be a problem if this is the stage of life where we seek to master the new skill of communicating interestingly to the public.
3. Expertise Creep: The Overreach of the Competent
Interestingness is not a general trait. It’s domain-specific. A good rule of thumb:
Interestingness = Expertise + Charm − (Overconfidence × Distance)
We’re capable of being interesting when we speak from deep knowledge. The further we drift from that knowledge, especially if we do so with too much confidence, the less interesting we’re likely to become.
This is the problem of expertise creep. It’s the mistaken assumption that adjacent expertise is interchangeable with deep expertise. Being experienced at energy trading doesn’t mean you’re instantly qualified to opine on federal energy policy. Running a successful company doesn’t instantly make you wise on leadership theory.
The boundary between domains isn’t always clear. The expert energy trader does have a huge head start on understanding energy policy, compared to most other people in the world. He’s not starting from scratch. But the danger lies in skipping the work—the slow, humbling process of acquiring adjacent expertise with the same rigor one applied to acquiring expertise in the original field.
A good way to illustrate this is to imagine how successful people would typically respond if they were given a big promotion at their job but asked, as part of it, to move into a sector that is adjacent to the realm in which they acquired their expertise and established their record of accomplishment. With their job, their reputation, and the material interests of their company or organization on the line, they would be pretty likely to move with great care and deliberation. They’d run small pilots, seek out mentors, test assumptions, and iterate. They’d treat the challenge with respect, and pay exquisite attention to the signals coming back toward them about whether they were getting it right or wrong as they went. It would take a while before they felt comfortable moving with the unconscious ease of genuine expertise when it’s earned.
When it comes to public communication, however, the same people often just go for it without much care or fear. They assume that because they’ve mastered one kind of thinking, they’ve mastered them all, or at least the ones that are conceptually nearby. This is why so many public figures end up sounding generic when they talk about politics, culture, or leadership.
The solution isn’t for everyone to stay in his or her lane. It’s to treat every new lane with the seriousness it deserves. To approach new domains with humility, curiosity, and the willingness to be wrong. To do the work.
4. The Advice Fallacy: A cognitive bias club sandwich
There’s a particular kind of cognitive and rhetorical failure that tends to occur when accomplished people are asked to distill their life experience into advice. They mistakenly assume that a) they know what worked for them, b) why it worked it for them, if in fact it did, and c) that whatever that is will work for others. This is the advice fallacy.
The advice-giver is retrofitting coherence onto what felt uncertain or chaotic when it was happening in real time. “Here’s what I learned,” they say, when what they’re actually communicating is: “Here’s how I now make sense of what happened to me.”3
That narrative doesn’t travel well. The successful entrepreneur who insists that “you just have to trust your gut” ignores the thousands of other people who trusted their gut and failed, as well as all the micro-instances when he either trusted his gut and failed or ignored his gut and succeeded. The person whose marriage improved after radical honesty assumes that candor always heals, not realizing it might destroy a different relationship built on diplomacy or reassurance. In many cases, the advice isn’t even an accurate distillation of what the advice-givers actually experienced, since people are quite good at self-deception and confirmation bias. Even when it is true to life, it’s usually nontransferable. It reflects temperament, timing, luck, and context.
If we’re wise, as listeners, we take such advice with a huge grain of salt. We identify what might be useful, hold it lightly, carefully test it as a hypothesis rather than recklessly implementing it. That’s not a bad scenario, on its own terms, but it doesn’t justify a speaker or writer committing the advice fallacy because it doesn’t take into account the costs of forcing your audience to do this kind of cognitive work of sifting through the dross of your advice for a few nuggets of gold. The fact that a motivated listener can extract something useful from your boringness doesn’t excuse being boring.
And that’s the best case scenario, one that probably gives too much credit to the receiver of the advice. The more realistic case is that people will do a poor job taking your advice with the requisite caution. They’ll commit various forms of advice receiver fallacies. They’ll ignore what they don’t want to hear. They’ll misinterpret what you say to make it sound, in their head, like affirmation of what they’re already doing. They’ll use it as a weapon to try to win an argument against someone else. They’ll try to listen but won’t really understand it well enough to integrate it constructively into their lives. They’ll listen but they also listen to three other pieces of profoundly conflicting advice, and end up indecisive and ineffective where they would have been better off decisively doing any single one of the four conflicting things they were advised to do. People are quite bad, in other words, at accepting advice well. It doesn’t make any sense to offer advice, no matter how good it is on its own terms, if it doesn’t take into account the myriad ways that people are likely to mis-hear it.
Finally, the typical style of advice-giving tends to produce visceral distress in the audience receiving it. It makes people feel bad about themselves, because it implies (or in some cases explicitly asserts) that success is the result of following clear principles. It turns what could be a shared exploration of how experience shapes understanding into a performance of mastery. It also just wastes people’s time. The listener leaves not enlightened but diminished.
Evolutionary psychologist David Pinsof has a great, and hilariously cynical, post on the ways advice-giving goes wrong. My favorite of his hypotheses is this one:
Advice is rarely focused on the goals we actually have. For example, here’s what the self-help section might look like if it was focused on our real goals:
Zen and the Art of Social Climbing
Echo-Friendly: 10 Steps to Ensconcing Yourself in a Cocoon of Ideological Conformity and Motivated Reasoning
The 7 Habits of Highly Effective Virtue Signalers
The Lips 2 Butt Method: Take Control of Your Life by Sycophantically Ingratiating Yourself with High-Status People
Own It: Keep Rival Male’s Sperm out of Your Mate’s Vagina
You Can Do It! How to Harness the Power of Moral Ambiguity and Plausible Deniability to Rationalize Your Fucked-Up Behavior
Eat, Pray, Confabulate
5. Underestimating the Challenge
There’s a widespread assumption, especially among high-achieving professionals, that being interesting in public is a natural extension of being good at what one already does. If you’re a skilled executive, respected academic, or successful entrepreneur, then surely you can talk about your work in a compelling way. But this assumption is almost always wrong.
The capacity to translate deep expertise into public-facing communication—speeches, interviews, essays—is not intuitive. It’s a separate skill. And it’s hard.
We tend to forget how much of our professional competence is tacit. Athletes, for instance, acquire their skill through repetition, improvisation, and embodied knowledge.4 They don’t necessarily understand what they’re doing in a way that lends itself to explanation. The same is true of visual artists, musicians, and craftspeople. Even in more overtly cognitive fields—law, medicine, academia, etc.—the expertise is often layered, contextual, and difficult to articulate.
This is why so many experts struggle to be interesting in public. They’re trying to explain something they’ve never had to explain before, in a format they’ve never had to master, to an audience they’ve never had to consider. And they assume it will come naturally, because they’re good at the thing about which they’re trying to convey wisdom and knowledge.
But public communication is its own domain. It requires a different kind of clarity, a different kind of rhythm, a different kind of empathy. It’s not enough to know your subject. You have to know how your audience hears it. You have to anticipate confusion, boredom, resistance. You have to select language that feels both lucid and fresh. You have to build a bridge between your world and theirs.
This is especially hard to recognize for people whose primary tools are already verbal—professors, lawyers, journalists, executives. Because they work in language, they assume they understand how language works. But the kind of language that succeeds in a peer-reviewed journal or a boardroom is not the kind that succeeds in a podcast or a public essay. It’s close, but not the same. And the difference is what makes the difference.
Most of us, if we’re fortunate, are good at one or two things. Maybe three if we’re extraordinary. To be good at yet another—being publicly interesting about the things we’re already good at—requires work. It requires risk. And it requires the willingness to admit that being interesting is not a personality trait (or not just a personality trait). It’s a skill.
4 Modest Suggestions
Before I give you my suggestions for becoming more interesting in public, I really want to stress the “modest” element of my four modest suggestions. I don’t think we know much that’s useful about how to deploy words to help people improve themselves. There are a ton of really straightforward things people can do to improve themselves along various axes, but it’s not all clear what you or I can say to each other to make it more likely that we will actually do these things in a sustained enough way to improve ourselves and our lives.
Do you want to lose weight? There’s a simple answer: Get on one of the new GLP-1 drugs. Do you want to be more fit? Exercise a lot. Do you want to have more luck with women? Stop being an asshole. Do you want to quit smoking crack? Stop smoking crack. And so on. Whole sections of our libraries and bookstores are full of books telling you how to do and be better, and no doubt many of them have helped people, but my strong intuition is that they’ve helped far less than the authors of those books think they have, and far less even than the people who think they’ve been helped have actually been helped. If that weren’t the case, why would such a high proportion of the buyers of self-help books be people who’ve already bought lots of other self-help books?
The darker truth, I’m pretty sure, is that these books are their own kind of drug, delivering hits of short-term success at self-mastery followed by lows of failure and self-loathing that need to be alleviated by more books and schemes, the totality of which feed into a broader cultural atmosphere that breeds or fuels many of the problems that the books that purpose to ameliorate.
I don’t think I’ve cracked the code on this, so let me just restate the overall thesis again, because it can’t be emphasized enough. We … don’t … know … much … about … how … to … deploy … words … to … help … people … improve … themselves. What we do know about how people change for the better, and even here there are severe limitations, is that it happens best through long-term, structured interactions with other people. Think AA, church, team sports, therapy, or having the good fortune to work in a really generative workplace. Words are an essential part of these structures, of course, but only a part, and not always the most important one. It is absolutely the case that books change people’s lives, but the mechanism through which that happens is incredibly mysterious and unpredictable.
So take these suggestions with a giant grain of salt and try to encounter them less as recommendations, per se, than as exploratory thoughts on what kinds of structures one might put in place, if possible, to allow for an increased possibility of interestingness.
Get Expert Help
Define your expertise and commit
Optimize Your Incentive Structure
Get therapy
1. Define Your Expertise and Commit
The good news is that if you’re really ruthless with yourself about distilling and defining the nature of the expertise you want to bring out into the world, the odds are surprisingly good that you’ll be one of the few people in that space with something interesting to say.
This is because there simply aren’t many people who can talk or write interestingly in most realms of human life. We don’t realize this because most of the public conversation happens in a very small number of enormously saturated conceptual spaces, and we naturally imagine ourselves as speaking publicly in those spaces. Sports. Politics. Sex. Relationships. Business.
But everything else, including a lot of things that are super important to a lot of people, is up for grabs. Even within those hypersaturated spaces, a lot is up for grabs. Is anyone really interesting on badminton? Probably not, but a lot of people love badminton. The world probably doesn’t need another expert in leadership, writ large, but what if you slice off a thin piece of it?5 Running meetings well, for instance. Are you good at that? Can you articulate to yourself not just what it is that you do, when running meetings well, but what other kinds of people with different styles and temperaments do when they run their meetings well? Do you know how to fire someone with dignity, or get underperformers to perform better? What about the art of defanging potential opposition within your organization through flattery and strategic requests for feedback?
Slice off a piece of it that you happen to do well and that you can really deconstruct and put back together, and then lean into that. Do your research. Look for other people who’ve written or spoken on the topic, and glean what you can from them. If you’re able to take all that and offer listeners and readers not just your own insight into the topic but a thoughtful tour of what other smart people with relevant experience have said, that’s a worthwhile service and vastly more likely to be interesting to others than almost anything else you’re likely to say.
Is there a big enough audience for this topic to make a career of speaking to it? Probably not. But you don’t have to. You’re already economically self-sufficient. You don’t need to support yourself and your family with this work. What you want, I imagine, is to connect with people who share your enthusiasms and commitments, and to have an impact on them.
Also, and I can’t stress this enough, you have to really enjoy thinking about the topic, whatever it is. I think it almost never works to try to reverse engineer what you should put out into the world, in this space, from what you think people want. Instead, select carefully from that small batch of topics that you’re passionate about, that you can’t wait to talk to people about, that you can imagine talking about for a decade. You won’t necessarily succeed, even if you nail this, but what’s the point of succeeding if you don’t even enjoy what you’re talking about?
2. Get Expert Help
The implosion of the journalism industry is a great opportunity to find collaborators relatively cheap. These are people (journalists) whose job has been to interview interesting people and then make their stories interesting. There’s no reason in principle they can’t do the same for you. Find a writer or producer whose work you like who seems underemployed and then offer him or her enough money to make it worth their while to collaborate with you.
This will only solve the problem, though, under certain conditions.
It has to be someone who has already shown that they can be interesting. There are plenty of pros who never rise to that level. They can help you get polished but probably can’t help you distill or discover your interestingness.
And it has to be a true collaboration, with a minimum of deference, for it to work. Most ghost-written books, speeches, etc. are boring because they’re just vanity projects for the subject, in which the objective is to put the shiniest, least controversial gloss on his story. A ghost writer can’t force his collaborator to be authentic. You need to demand it of them and demand of yourself the vulnerability to take influence.
This means you’re looking for someone with a specific and somewhat rare combination of traits: genuine skill at the craft, enough professional confidence to push back against you, and sufficient emotional intelligence to do so without making you defensive. The point is to create a space where you can be uncertain, exploratory, even a little embarrassed—where you can say the thing you’re not sure you should say, and not say the thing you want to say but shouldn’t say. One of the key challenges is figuring out how to calibrate the voice just right – how to be open without coming across as self-indulgent, flawed without seeming unappealing, and authoritative without seeming arrogant.
A great example of this working well is the collaboration between Andre Agassi and Pulitzer Prize-winning journalist J.R. Moehringer on Agassi’s memoir Open, one the great sports autobiographies of the past few decades. There’s a good 2009 New York Times profile of their partnership where the two describe a process that was genuinely collaborative in ways that most such arrangements never are.
The backstory, basically, is that Agassi read Moehringer’s memoir, The Tender Bar, and loved it so much that he called Moehringer and proposed they work together. Moehringer was initially quite skeptical, presumably because he didn’t want to be a celebrity stenographer, no matter how much money was on the table. Agassi was persistent, though, and eventually persuaded Moehringer that he would genuinely put himself in his writerly hands.
Moehringer describes their early conversations, after agreeing to collaborate, as “painful,” with Agassi “completely locked—stilted, resistant, halting.” Agassi had an incredible memory of the details of his tennis matches, but almost nothing useful to say about his personal life or interiority. Gradually, he loosened up, but the process of getting there was difficult for both of them.
“I have a lot of capacity for pain,” said Agassi, “but I didn’t understand how hard this process would be.”
The result is a book that is honest and interesting in ways celebrity memoirs almost never are. It also, somehow, has a voice that feels like Agassi’s even though Moehringer was the one who was sitting down at the computer and doing the sentence by sentence writing.
This is what a real collaboration looks like: not a service provider executing the client’s will, but a partnership in which both parties bring something essential and neither can fully control the outcome. It requires the expert to push, and it requires the subject to be pushed, and vice versa. Most people aren’t willing to subject themselves to this kind of process. That’s why most memoirs, speeches, and public personas are forgettable.
Most people also can’t afford, or don’t want to pay for, a writer of Moehringer’s skills. But it’s a useful model, though. Look for a good writer or producer who needs work and then pay them well enough to really buy their genuine commitment. Start with a small project – a one-off podcast episode or speech or essay – and see how it works.
The economics of this arrangement, it should be noted, will tend to go wrong in one of two ways: either you’ll underpay and get someone who is too junior or too eager to please to serve a real partner, or you’ll overpay for prestige and get someone who’s coasting on reputation and won’t do the unglamorous work of dragging the interesting stuff out of you. What you want is someone hungry enough to care but established enough to have developed a real point of view about what makes for compelling public communication. They exist. They’re not always easy to find. Let me know if you need help finding someone, and I’ll see what I can do. (I’m not trawling for work for myself; I’m too busy with my own stuff.)
3. Optimize Your Incentive Structure
I almost didn’t include this suggestion, because I fear it’s one of those pretty useless pieces of advice, like telling a crack addict not to smoke crack, that simply doesn’t take into account the immense difficulty of fundamentally altering your habits. I’m going to include it, though, because I think there are at least minor things you can do in this space that don’t require a ton of deep habit modification.
So here it is: create a structure around yourself where the incentives and disincentives are aligned with your goal of being interesting. Launch a substack or podcast, and let the metrics tell the tale. Ask for anonymous feedback on whatever it is that you’re putting out in the world (a speech, a podcast, an essay). Set goals for yourself that you can’t reach based merely on your status or reputation.
The specific structure will look different depending on who you are, but the key factor is not allowing yourself to exist solely in an ecosystem where you will receive positive feedback for your thing even if you’re being boring.
And if you are receiving mostly or entirely positive feedback, be extremely skeptical of it.
This is really hard stuff. Most of us, if we’re lucky, are blessed with two or three things we’re good at in life (our job, for instance, and being a friend, or a father, or a little league coach). To be good at yet another thing–-being interesting in public—is possible, but the odds are against you, and even more so the earlier you are in the endeavor. Best case scenario is that it will take a while to get consistently interesting, and that early in the game the most that you can hope for are flashes of interestingness surrounded by longer stretches of boringness. So approach it with the expectation that it will be hard and that you’ll have to go through multiple cycles of feedback and iteration. The only way that those cycles will actually assist you in becoming better, in most cases, is if the incentives and disincentives are properly aligned.
4. Go to Therapy
I don’t know how going to therapy will help you become more interesting, because the therapeutic process, if it leads to that result, is so dependent on the specific issues and baggage and strengths and idiosyncrasies that you bring to the encounter.
What I can say, with some confidence, is why it might help—even if the how is yours alone to figure out.
Go back to the first risk I described: internalized politics. The caution that makes people boring in public isn’t just a professional habit. It’s usually a psychological one too, and often one that in some sense goes back to your childhood. All of us, by virtue of being human, are colonized by the voices of other people as well as our own doubts, insecurities, illusions, and misperceptions. The good news is that all the crazy shit under the hood is the wellspring of what makes us interesting and surprising. The bad news is that it can also keep us locked up.
Therapy is one of the few structures in our society that is explicitly designed to unlock us, pry open some of the closed off boxes, shake up the etch a sketch a bit so that we can become something different. It’s an invitation to a conversation with oneself, and in general the richer the quality of that internal conversation the more interesting and generative our internal presentation has the space to be.
You can hear in the work of many of the writers and speakers we find most compelling a sense that they’re genuinely wrestling with something, that there’s a person behind the presentation who has doubts and confusions and unresolved business. Therapy is, among other things, a forced, structured encounter with one’s own ambivalence, contradictions, and capacity for self-deception.
There’s another mechanism here worth naming. Our psychological defenses—the ones that protect us from anxiety, shame, and unresolved conflict—don’t just make us guarded in conversation. They make us repetitive thinkers. A defense routes our attention away from threatening material and back toward the familiar, the settled, the pre-narrated. Over time this becomes less a conscious act of avoidance than a kind of cognitive default. We return, again and again, to the same handful of stories about ourselves, the same explanations for why things turned out the way they did, the same implicit theories of how the world works. It’s a simulation of thinking, a re-running of conclusions we reached years ago, dressed up to look to ourselves like reflection.
This is, in fact, may be the deepest source of public dullness. People have simply stopped generating new thoughts about themselves and their experience. What you get when you watch them in public is not someone thinking but someone reciting, however fluently, from a box set of the classics. The world is just a series of prompts: play disc one, track three; play disc four, track eight.
Therapy, at its best, introduces friction into the mental grooves that have grown too deep. The goal isn’t to take what you’ve learned about yourself in therapy and put it out in public, though for some people that could be interesting. It’s less direct than that. You trust the process, as therapists like to say. As you develop a richer relationship with your own experience, and learn about yourself in relation to the therapist, you’re just more likely to say or write richer feeling things when you step out in public. You’ll notice new and different things about the world. The quality of your relationships with other people will change. All of this, somehow, in ways neither you or I can predict, is likely to make you a more interesting person in the world. It just will.
To be clear, therapy is not the only path to this kind of growth. It could be religious practice, meditation, deep relationships with other people, sustained service to a cause other than yourself. Therapy is the vehicle that I know best for this kind of work, so it’s what I’m recommending, but the deeper recommendation, perhaps, is that one should try to keep growing as a person. It’s worthwhile on its own terms, of course, but it is likely to make you more interesting as well.
Finally, I suspect it goes the other way as well. As we genuinely endeavor to be more interesting, and less boring, along any and all of these axes I’ve identified, we’re training ourselves to be deeper people—more thoughtful about how others hear us, less likely to deceive ourselves, more open to candid feedback, more humble, more courageous, more desirous of genuine connection.
We should try to be more interesting because interestingness is a virtue in its own right; it makes the world richer, more vital. But also because it’s one way–not the only one, but a good one–to pursue the good life.
There was a fascinating response by Luke Ford to my bit on how Barack Obama, despite having been quite interesting in the past, was boring on the final episode of Marc Maron’s podcast.
He draws on “alliance theory,” which was laid out in a 2023 paper by David Pinsof, David Sears, and Martie Haselton. People stop being interesting in public when their primary cognitive task shifts from truth-seeking to alliance maintenance.
Here’s Luke on why, as alliance theory would predict, Obama stopped being as interesting as he once was:
People stop being interesting in public when their primary cognitive task shifts from truth-seeking to alliance maintenance.
Once you see that, Obama-on-Maron stops being puzzling and becomes almost inevitable.
High-status people are alliance managers first, thinkers second. Obama is no longer an individual mind speaking freely. He is a symbolic coordination node for multiple overlapping alliances: Democrats, liberals, Black Americans, global elites, donors, institutions, legacy media, history itself. Every public utterance is evaluated not for insight but for coalitional consequences.
Alliance Theory predicts that in this position, cognition itself changes. Internalized politics is internalized alliance defense. The essay describes “internalized politics” as caution becoming habitual. Alliance Theory sharpens this. Over time, the brain stops generating thoughts that would create alliance risk. Not because they’re false, but because they are dangerous signals.
Interesting thoughts are almost definitionally risky.
They create surprise.
They violate expectations.
They reveal internal conflict.
They create ambiguity about loyalties.
Alliance Theory predicts that people who depend on large coalitions will unconsciously suppress such thoughts before they reach articulation. The filter moves upstream. As the essay puts it, “the mask becomes the face.” Pinsof would say: the alliance model becomes the mind.
Why Obama was interesting before and boring now. Early Obama had something to gain and little to lose. Risk signaled authenticity and differentiation. Later Obama became a coordination anchor. His job was to stabilize, not explore.
On Marc Maron’s podcast, there was no alliance upside to risk-taking. Only downside. So his cognitive system defaulted to the safest equilibrium: platitudes that offend no ally, threaten no legacy, and create no defections.
Alliance Theory predicts this exact outcome.
Audiences crave signals of truth-seeking, vulnerability, and exploration because those signals indicate low alliance calculation. We intuitively read risk as honesty.
When someone speaks in a way that feels fully pre-cleared, we experience it as dead. Not because it’s false, but because it is pure coordination output rather than discovery.
Interestingness is anti-coalitional. This is the uncomfortable implication. Being interesting in public usually requires temporarily suspending alliance management. It requires being willing to look wrong, partial, or disloyal.
Thanks to Daniel Muñoz for pointing out that this whole paragraph is quite boring, and is boring, ironically, because it is the result of a conceptual error that high status people tend to make when stepping out into public. It’s wasting words to establish one’s authority when it’s the rhetoric itself that has to earn authority with the audience.
As it happens, I have two pieces of advice that I give to new parents, based on my experience as a father of three. The first, “Oppenheimer’s one point plan for parenting,” is derived from research that the psychologist John Gottman did on marital happiness in the aftermath of a first child. Gottman found that roughly two-thirds of couples ended up less happy with each other a year after the new baby arrived, while the other third ended up with an improved relationship.
The main difference between the two sets was whether the secondary caregiver (usually the dad, in hetero couples) spent enough time alone with the baby. It only had to be a few hours a week, but it had to be on his own, away from the primary caregiver (usually mom). If he did this, a virtuous cycle ensued. He developed competence in caring for the baby, as well as a distinct relationship to it. The mother got some time alone to decompress, and she learned to trust her partner as a parent. The baby became a shared project of the couple. If the burden of care fell entirely on the mother, however, the mom began to resent the husband for not helping more. The husband felt judged by the mother for his lack of competence with the baby, and eventually a two-tiered system developed, with mom and the baby on the inside and the dad orbiting around, resentful of his exclusion, angry that his wife wasn’t paying more attention to him, and disconnected from his child. So the advice is simply to make sure that dad spends those few hours a week caring for the newborn on his own. That’s it.
My other piece of advice isn’t advice at all, but rather a parable, which I call “The Parable of the Target Parent.” It goes something like this: One day soon you will be in Target and you’ll see a parent roughly dragging his or her screaming child out of the store, and you’ll think to yourself something like, ‘What a terrible parent. I would never treat my child like that.’ Then on a different day, maybe even in the same Target, you will be the parent roughly dragging your screaming kid out of the store. You will see other people looking at you judgmentally, and you’ll think to yourself, ‘Goddamit, I’m a good parent. You don’t understand how hard I work, how much I love my kids, what an awful day I’ve had, and what a little shit he’s being. Stop judging me! Fuck you!’ Then some other day, you will once again be the one watching someone else drag their kid out of Target, and you will have learned absolutely nothing. You will judge them to be a terrible parent and feel superior to them.
I don’t know if either of these have ever helped anyone, but I enjoy sharing them. :)
Philip Trekker says, per this:
I’m reminded of the David Foster Wallace essay (”How Tracy Austin Broke My Heart”) about why a tennis star’s autobiography was so boring. Maybe they speak in dull banalities because their talent lies elsewhere. Or maybe they believe them so sincerely that they are actually part of what makes them successful.
“The real, many-veiled answer to the question of just what goes through a great player’s mind as he stands at the center of hostile crowdnoise and lines up the free-throw that will decide the game might well be: nothing at all. . .It may well be that we spectators, who are not divinely gifted as athletes, are the only ones able truly to see, articulate, and animate the experience of the gift we are denied. And that those who receive and act out the gift of athletic genius must, perforce, be blind and dumb about it - and not because blindness and dumbness are the price of the gift, but because they are its essence.”
Adam Mastroianni’s recent post on “underrated ways to change the world” has this suggestion, which feels very aligned with what I’m saying above:
1. ANSWER AN IMPORTANT BUT UNSEXY QUESTION
According to this terrific profile, Donald Shoup “has a strong claim on being the scholar who will have had the greatest impact on your day-to-day life.” Shoup did not study cancer, nuclear physics, or AI. No, Shoup studied parking. He spent his whole career documenting the fact that “free” parking ultimately backfires, and it’s better to charge for parking instead and use the revenues to make neighborhoods nicer: plant trees, spruce up the parks, keep the sidewalks clean.
Shoup’s ideas have been adopted all over the world, with heartening results. When you price parking appropriately, traffic goes down, fewer people get tickets, and you know there’s going to be a space waiting for you when you arrive.
Many so-called “thought leaders” strive for such an impact and never come close. What made Shoup so effective? Three things, says his student M. Nolan Gray:
He picked an unsexy topic where low-hanging fruit was just waiting to be picked.
He made his ideas palatable to all sorts of politics, explaining to conservatives, libertarians, progressives, and socialists how pay-for-parking regimes fit into each of their ideologies.
He maintained strict message discipline. When asked about the Israel-Palestine protests on campus, he reportedly responded, “I’m just wondering where they all parked.”
So the next time you find a convenient parking spot, thank Shoup, and the next time you want to apply your wits to improving the world, be Shoup.
Years ago a dear friend of mine who is herself a very interesting person, perhaps because she graduated from St. John’s College which in my experience punches above its weight in producing interesting people, told me: “to be interesting is to be interested.” This essay made me think how true that is. Stay curious, stay humble, and leave room for surprise.