The interesting thing about interesting things
Interestingness isn't random—it has 12 repeatable types
“I am bored by most of what I read. You have to amaze me. Tell me something that I have no idea about in a way that I’m going to find surprising. That’s my first principle to writers.” – Kevin Kelly
WHAT MAKES a piece of writing interesting? If you said “good storytelling,” I wouldn’t fight you over it. Stories are unmatched at capturing our imagination. If you said “a strong writing style,” I might start to split hairs with you. But if you’ve ever read Hunter S. Thompson or Heather Havrilesky1 and wondered how they manage to make the mundane sound so compelling, then style is admittedly a good shout.
But actually, what makes a piece of writing truly interesting is the degree to which it challenges our taken-for-granted assumptions. The more entrenched the assumption, the more animated we are when a writer challenges it. And if what they write doesn’t challenge but only affirms what we already know, well, then, we’re likely to say, “No shit Sherlock! Tell me something I don’t know.”
If you care about writing stuff that gets talked about, then you should turn interestingness into a study. In this post, I’m going to look at how some of the most accomplished writers have done it—from Sigmund Freud to the latest Substack bloggers—in the hope that you (the writers among you) and I might learn how to write more interestingly ourselves.
Index of the Interesting
This post is inspired by a dense fascinating sociological paper2 by one Murray S. Davis published in 1971. Davis wanted to know what made some social theories capture peoples’ imagination, even when they weren’t true, whilst others faded into insignificance never to be noted (or, more precisely, never to be footnoted).
By analysing the works of writers like Freud, Marx, Nietzsche, and Durkheim across disciplines like sociology, psychology, and political economy, Davis' research revealed that writing is at its most interesting when it refutes—or at least disputes—peoples’ existing beliefs.
In other words, it’s not enough just to present new information readers didn’t have before. To write something truly interesting or even fascinating, your ideas must negate beliefs they already have.
Davis, god bless him, went on to identify 12 "species" of interestingness—and he organised them neatly into what he called the Index of the Interesting.
Whilst each species describes a different way to surprise people, the one thing they all have in common is that they negate an accepted belief. "What seems to be X is in reality not X."
Here are the names of Davis' species of interestingness:
🧩 Composition
🌐 Abstraction
🌍 Generalization
🔄 Stabilization
⚙️ Function
⚖️ Evaluation
🔗 Co-relation
🕊️ Co-existence
📈 Co-variation
⚡ Opposition
🔁 Causation
🗂️ Organisation
It’s all a bit academic. But to make it more palatable, I’ve sourced writerly examples of each species and shared them below.
I’ve written some thoughts about the first species—Composition—in order to give you a way into Davis’ theory. With the other 11, I’ve simply provided a definition along with an example.
🙋♂️ If you can spot where some of your favourite pieces of nonfiction fit into these 12 categories, please, share them in the comments section. The more examples we have to illuminate the species, the better chance we eager writers have of understanding how to use them.
Species #1: 🧩 Composition
Here is Davis' definition of the Composition species (don’t worry, I’m only gonna give you one of these jargony definitions):
“What seem to be assorted heterogeneous phenomena are in reality composed of a single element—or what seems to be a single phenomenon is in reality composed of assorted heterogeneous elements.”
Basically, what’s he’s saying is that something’s interesting if it shows us that what we thought were a bunch of unrelated things are actually related—or vice versa.
Sigmund Freud, for instance, argued that things like how kids behave, how people act in groups, dreams, jokes, and even silly slips of the tongue are all influenced by the same basic instinctual drives in the subconscious. By saying this, Freud negated peoples’ prior assumptions that those phenomena were unrelated—and this, Davis said, was what made the idea so interesting.
It didn't take me long to find other writerly examples of this Compositional interestingness.
One of the reasons behind Jonathan Haidt's impact with his book about mobile phone addiction (The Anxious Generation) is that he's showing how one phenomenon—phones—is at the root of so many problems that we previously thought were unrelated, from the increase in cyberbullying and addictive behaviours, to a loss of creativity and boredom tolerance, to shorter attention spans and feelings of inadequacy.
Marshall McLuhan’s book Understanding Media looked at various forms of communication and distilled the phenomenon of globalisation into a unified concept he called the "global village." He argued that new forms of electronic media—mainly television and the internet—compressed time and space, creating a world where people were more interconnected than they first thought.
Thinking about my own experiences, I wondered: What in my life could be related that doesn’t appear to be? Is there a principle or a pattern that seems to show up everywhere and is quietly at work behind the scenes?
Here’s one example: I often find myself caught in tensions that feel somewhat familiar, like, for example, when I’m trying to decide between:
finding a restaurant intuitively by wandering—or by filtering top rated spots on Google
starting a new essay—or working on an old draft
looking for new jobs—or finding ways to double down on existing ones
On the surface, none of these choices seem related, but they're all driven by the same fundamental dichotomy: whether it’s better to explore or to exploit—and the trade off between seeking novelty and deepening familiarity would probably make interesting essay material.
The Composition species, then, says that writing interesting pieces isn’t just about telling good stories or writing with a fiery tone; it’s about showing readers that things they thought were unconnected are actually connected—or things they thought were already connected are actually not.
What about you? Does anything in your life fit this pattern?
On the side of the minority
Overall, you might feel that this method of challenging assumptions is uncomfortable. There is something contrived, or even crude, about the prospect of going hunting for assumptions to challenge, or challenging assumptions just for the sake of it, especially if they bear little relation to the topics you normally write about.
But, if you’ve written a lot, you know that you often don’t know what you really believe until you’ve tried writing about it. And so even the most randomly chosen assumption could turn out to be a worthy creative project, and a commitment to understanding a topic more intimately. As far as I can tell, that ain’t a bad use of your time as a writer.
Even more than that, it’s precisely the beliefs people take for granted that we should examine the most because ideas ossify, they become problematic. The most common assumptions of all are also the most under-explored terrain for writers. If you insist on writing about AI or personal development, that’s fine. But understand that you’ll have to share the pool with every other Tom, Dick, and Harry with an internet connection and a LinkedIn account. If you can find ways to challenge accepted beliefs, on the other hand, then you’ll be the biggest (or the only) fish in the pond.
“Whenever you find yourself on the side of the majority, it’s time to pause and reflect” – Mark Twain
After binging on Davis’ paper and searching for illustrative examples, three insights came up for me that I think could prove helpful when trying out these species as writers:
Whilst all interesting things are novel, not all novelty is interesting, which means that to write truly compelling stuff, we have go beyond simply presenting new information.
Knowing our audience seems important because without understanding their assumptions we can't effectively challenge them. We might think we’re writing something surprising, but our readers might think it’s pretty obvious.
We shouldn’t worry so much about AI replacing us writers because interestingness comes from violating expectations, which AI’s bad at. It tends to reinforce patterns rather than break them, and it excels at consensus but struggles to create surprises.
Without further ado, for your intellectual pleasure, courtesy of Mr. Davis, here are the other 11 species of interestingness, with a modern nonfiction example to bring them to life:
#2: 🌐 Abstraction
A piece of writing is interesting if it reveals that something which seems systemic is actually rooted in individual actions—or that something which seems personal is actually part of a bigger system.
Example: Cities and Ambition by Paul Graham looks at how our cities have a subtle but profound impact on who we end up becoming, revealing that what feels like a personal ambition is often shaped by the culture and values of the city we live in. Individual aspirations are intertwined with the larger systems around us.
#3: 🌍 Generalization
A piece of writing is interesting if it takes something assumed to be universal and shows that it’s actually specific to one group—or it takes something specific and shows that it applies to a much larger group.
Example: How to Be Great? Just Be Good, Repeatably by Steph Smith generalises a broad truth about success: what works for one field often works for another. The lessons of deliberate practice and compounding effort apply universally, not just in one niche.
#4: 🔄 Stabilization
A piece of writing is interesting if it shows that something chaotic and unstable is actually surprisingly steady—or that something stable and unchanging is actually fragile.
Example: The Cloud Under the Sea by Josh Dzieza dismantles the perception that the internet is an invincible entity by telling the story of the delicate undersea cables that make it all possible. It uncovers how dependent the web is on physical infrastructure, vulnerable to damage from natural disasters, ship anchors, and even shark bites.
#5: ⚙️ Function
A piece of writing is interesting if it shows that something which looks broken actually works well (or vice-versa)—or that something which appears to function in one way actually functions in another way.
Example: Research as Leisure Activity by Celine Nguyen reframes the role of research. Research is typically seen as a serious, goal-oriented activity done in academic settings to produce concrete outputs. Her essay flips this by suggesting that research can be personal, joyful, even playful!—something done for its own sake.
#6: ⚖️ Evaluation
A piece of writing is interesting if it shows that something seen as bad is actually good—or that something seen as good is actually bad.
Example: How Empathy Makes Us Cruel and Irrational by Gurwinder Bhogal argues that empathy, instead of leading to compassion and justice, often results in bias, gullibility, and dishonesty. It’s a direct inversion of the common belief that empathy is inherently good or morally superior.
#7: 🔗 Co-relation
A piece of writing is interesting if it reveals unexpected connections between things that seem unrelated—or shows that things assumed to be connected are actually independent.
Example: The Friendship Dip by Anne Helen Peterson explores the relationship between external societal factors (eg, productivity culture, parenting norms) and internal experiences of friendship decline. It highlights unexpected correlations, such as how overworking to secure a "better future" paradoxically leads to weaker social connections.
#8: 🕊️ Co-existence
A piece of writing is interesting if it shows that things which seem to fit together actually don’t—or that things assumed to be incompatible actually work well together.
Example: This is one of two species I couldn’t find a modern example for. If you do, please let me know and I’ll add it here and credit you—thanks! (Davis’ example was of Denis de Rougemont’s book Love in the Western World which asserted that love and marriage, which everyone thought were compatible, actually were not.)
#9: 📈 Co-variation
A piece of writing is interesting if it shows that a relationship that looks positive is actually negative—or that a negative relationship is actually positive.
Example: When I have a slower publishing cadence my blog grows faster by Henrik Karlsson argues that writing effort and success actually have a positive co-variation: the more time spent refining a piece, the greater the exponential returns in terms of reader engagement, subscribers, and overall impact.
#10: ⚡ Opposition
A piece of writing is interesting if it reveals that things which seem similar are actually opposites—or that things which seem opposite are actually similar.
Example: Another species I couldn’t find a modern example for. Can you? (Davis used the example of Eric Hoffer who asserted in The True Believer that the psychological motivations of people joining opposing social movements are in fact the same. And George Orwell was pretty good at this species too in his books with ideas like “freedom is slavery,” “War is peace,” and “Ignorance is strength.”)
#11: 🔁 Causation
A piece of writing is interesting if it flips the assumed cause-and-effect relationship, showing that what looks like the cause is actually the effect—or vice versa.
Example: You’re Not Burned Out, You’re Doing Work You Don’t Give a F*ck About by Tim Denning argues that what we think of as the cause of burnout (overwork and productivity culture) is actually the effect of a deeper problem: doing work you don’t care about. This inverts the causal relationship and reframes burnout as a symptom rather than a root issue.
#12: 🗂️ Organisation
A piece of writing is interesting if it shows that something which seems well-organised is actually chaotic—or that something unorganised actually has structure.
Example: This very post is a good example (humblebrag!). If you’ve read this far, then either you have a masochistic tendency to read things that don’t interest you, or your starting assumption was that interestingness couldn’t be structured.
I can’t help quickly sharing 3 more examples. I’m seeing them everywhere! Can you guess which species they are?
SneakyArtist
recently posted a Substack Note that said, “Beauty must be believed to be seen.”The Cultural Tutor said, “If you want new ideas, you should read old books.”
Futurist Kevin Kelly, who I quoted at the start, said, “Don’t be the best, be the only.”
Thank you Mark at , Vi at , Dominik at , and Corina for helping me with this.
My top posts of 2024
500 of you have joined since this time last year—thank you and welcome! Here are my top posts from 2024 in case you missed any.
I published fewer pieces this year, focusing on spending time with ideas until they felt complete rather than sticking to a schedule.
It was a bit of a risk since some studies suggest quantity breeds quality, but I decided to ignore that rule. I love writing too much to lose momentum, and I wanted the space to experiment with new forms like listicles and satire.
Here’s what I’m especially proud of writing this year:
Thread Boi Writing System™️ | Your readers no longer have the patience for paragraphs. Act accordingly.
The issue isn’t awkwardness—it’s a lack of curiosity | Curiosity cures everything. The clue’s in the name.
Why coffee is nuts | And I ain’t talking about pistachio syrup.
Internet Tour Guides | We may’ve been born too early to explore the universe, but we’re just in time to explore the internet.
The world is your oyster. But… | It comes at a worthwhile price.
All the million-dollar-winning questions from Who Wants to be a Millionaire | Feel free to skip this if you don’t like quizzes.
You’re terrible with names | So here are some ways to find them out without giving the game up.
He’s a Twitter Sensation | Here’s why.
Here are 30 killer opening sentences | Mastering the mental itch.
Hire me as your Writing Mentor 👨🏫 | I’m now helping essayists and bloggers get better at their craft.
Thanks for reading, folks!
Harrison 🙋♂️
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IMO the best (and funniest) post where Heather transforms the mundane into something special is her post about New York Times reviewers.
#12 made me think of Joan Didion. I read The White Album. Specifically, the essay "Bureaucrats." In it, she visits a traffic control operations center that controls one of the major highways in Los Angeles in the 1960s. The essay reveals the absurdity of bureaucratic systems and their ineffectiveness in managing freeway systems. Great post! Thanks for sharing.