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Before we entered the Age of Emoji, I never quite liked the quote “life is a comedy to those who think, a tragedy to those who feel.” But now I kinda do. Emoji have been a bit of a life changer for those of us who are not naturals at this feeling game. Turns out, they function as pretty good theater masks in the sense of Keith Johnstone (in particular the chapter on masks and trances). If you follow me on Twitter or Facebook, you may have noticed that my current avatar is this hand-crafted, emoji-mashup version of the classic theater-masks icon/emoji 🎭, (which seems to have turned into a generic overloaded symbol for the performing arts). Since adopting this avatar, I have become a better human being: full of compassion, less inclined to troll, more willing to listen to Trump supporters, etc.

Here’s the thing, if you routinely use emoji, especially on Twitter, you will notice that you actually feel the emotions represented, at least weakly. It’s like color-by-numbers feeling. Since emoji seem to be used ironically as often as they are sincerely, using emoji is like learning an emoting alphabet, in regular and italic (=ironic) forms.

I suspect it is my emoji (over)use that has gotten me interested in one particular feeling lately: weirdness. By my account and understanding of it, weirdness is not so much a feeling as that state of not knowing what to feel. There can be no static emoji for it. At best you could make an animated gif that cycles through several emotions to represent the state of emotional indeterminacy that is ‘weirded out.’ I’d put 😟, 😦, 😐, and😠 in the cycle (note, depending on where you read this post, these may not render exactly as I intend, which is part of the fun). You can say more: weirdness is also the experience of not knowing what to think.

The experience of weirdness, and the condition of not knowing what to think or feel, but engaging life in that state anyway — what I call speaking weirdness to truth — is perhaps the soul of gonzo, if not its body. Speaking weirdness to truth is the lowest-effort way to pull off the Hunter S. Thompson life anti-script: when the going gets weird, the weird turn pro.

Beyond Tragedy and Comedy

The idea that life is a comedy to those who think, a tragedy to those who feel, presupposes that we know what to think or feel about a situation.

To be able to think, for instance, means that the situation evokes at least some rudimentary mental models. Maybe they’re the wrong ones, but all thinking needs is a place to start. That whole “give me a place to stand and I will move the earth” thing.

To be weirded out is to sense no firm ground beneath your feet. Mental models cannot work as a leveraged way to experience something without some such firm ground.

To be able to feel about a situation means there is a discernible bias, an overall coloring, to the emotions evoked. You may need to do some advanced black-belt-empath feeling to figure out whether you feel type 18a outrage or type 7b sadness, but if you’re all over the map, and literally don’t know whether to laugh or cry, it means you don’t know what to feel.

To be weirded out is to feel no emotional orientation, no true north in your standard feeling-compass. Here is a standard feeling compass, made up of the 6 basic emotions of joy, sadness, fear, anger, surprise and disgust.

If you can’t match the words to the faces, you have low emotional literacy; I am not that bad an artist. Incidentally, I made these faces a few years ago when I was exploring making a conversation game with some friends. Nothing came of that project, but I have these assets left over so I’m using them.

I don’t have a similar graphic for thinking, but my holy-grail animated-gif weirding emoji would have some mix of cycling through various thinky faces and feely faces. To represent the compass needle on both swiveling around wildly.

Somebody make a thinky-feely animated-gif schrodinger emoji.

Anyhow.

The Inner Game of Weirding

Weirdness is a characteristic of external realities that creates emotional and intellectual indeterminacy in your internal realities. It is more than merely the feeling of ambiguity or uncertainty, which I’ve been talking about a lot lately.

Ambiguity is not being sure which interpretation of a situation is the correct one. But you’re fairly sure the situation is covered by the set of mental models in play. It’s either a duck or a rabbit, or some deliberately ambiguated thing in between.

Uncertainty is not having all the relevant data to flesh out a picture, but you’re fairly sure you get the picture itself. It’s a stock market, and with high probability, the stock will go down, but you don’t know how far and how soon. That’s uncertainty. You’re not trying to decide whether it is a duck in a rabbit warren or a stock in a stock market.

Weirdness though…

Weirdness is a deeper sense that you are encountering the truly unknown-unknown. Chances are you cannot even sort out what part is ambiguous and what part is uncertain. You can’t tell whether more data will help, and if so, how. Weirdness is meta-ambiguity and uncertainty if you like, where you can’t tease apart the ambiguity and uncertainty in a situation. This gives me an updated, cleaner version of my uncertainty/ambiguity 2×2 from the link above, woohoo:

Take the Harambe meme for instance. I recently wrote a piece about it in The Atlantic. That’s weirding. You probably don’t know quite how to think or feel about it, and you’re not sure if seeing more examples will actually help much, or how. Another great example is this recent xkcd, which highlights the need for imagination and creativity in dealing with weirdness:

Truth and Weirding

Weirding is a portent of deeper truths. When you are feeling weirded out, it’s a sign that your truths are about to get undermined by deeper ones by a crash. It is a lead indicator of impending expansion not just in what you know, but how you know it. Weirdness presages a catastrophic evolution in the categories and modes of knowing.

It is your brain signaling that it needs a reboot. Something like this image is going on:

Most people keep clicking “remind me later” and hope they are never forced into it.

Nobody wants to interrupt the smooth functioning of their brain to reorient intellectually and emotionally.

Which means the weirdness accumulates. And accumulates. Until something breaks and there is a crash.

This leads me to what is possibly my cleverest snowclone from the last six months. With apologies to Benjamin Graham, in the short term life is a sentiment voting machine, in the long term, it is a weirdness weighing machine.

Weirdness as Abstraction Leaks

Thinking implies mental models. Less obviously, emotions also imply mental models. I only dimly recognized this back in 2011 when I first wrote extensively about mental models in Tempo. Back then, I saw emotion as primarily a sort of coarse modulation shaping and guiding the intuitive System 1 side of thinking. Sort of a bass-guitar support to the lead vocals of thinking. Naturally, Tempo was a hit among those who think, a flop among those who feel. My new theory is that emotions and feeling constitute a complete and parallel locus of lead cognition. Hence the T/F dichotomy in the Myers-Briggs test. If this theory is correct, the second edition of Tempo should sell twice as well whenever I get around to writing it.

Whether they are thinking models or feeling models, mental models are by definition finite and wrong. Here’s the thing though: many people who like to trot out the George Box quote, “all models are wrong, some are useful” have never truly experienced mental models going wrong. They imagine it will feel like a certain critical weight of countervailing evidence accumulating, followed by some sort of reasoned swapping out an “falsified” model for a superior one. A sort of philosophical analog to trading the null hypothesis for the alternative hypothesis in some statistician’s utopia.

No, it’s a critical weight of weirdness accumulating in your mental climate, under the tumult of everyday emotional weather, followed by a crash.

So when your mental models get undermined, you experience a crash of greater or lesser severity, in the same sense that your computer experiences a crash. Depending on the type of computer you have, it may feel like either a blue screen of death, an automatic reboot sequence starting (which will look like gobbledygook on the screen if you’ve never rebooted since birth), or some sort of safe-mode recovery routine with a cryptic prompt to choose between options you don’t understand.

What it doesn’t feel like is a rational process of in-control “changing your mind.” This is because your mental models are also your identity. I’ve never met anyone who has ever peacefully changed their mind on anything in which they have significant identity investment. All I’ve seen is people crashing and recovering, with various degrees of religious transformation. I covered a subset of such transformations in The Cactus and the Weasel.

Let’s add some more detail. The anatomy of every crash is usually unique, and you need a good deal of domain-specific troubleshooting experience (with brains or computers or whatever) to actually navigate them, but they do have some common features.

The biggest common feature is that crashes are generally associated with abstraction leaks. An abstraction leak is when a mental model or models get undermined by a more fundamental level of reality or truth breaking through the model boundaries. In the simplest case, there is a clear “up” and a “down” determining a stack of abstraction levels from highly phenomenological to highly metaphysical. Here is a picture that I was actually making for another post (all the images in this post, oddly enough, were made for other purposes).

It is wrong, but useful for this discussion. You should be able to grok the left-hand side image at least. The right hand side is very useful if you understand computers well enough to parse it. Computers, which we made in our image, wonders to perform, serve as good, if stylized, mirrors of our models of mind. You may enjoy the twitter conversation sparked by this drawing a few days ago.

Troubleshooting as Weirdness Praxis

A cheap and easy way to experience weirdness, and get better at navigating it, is to try and troubleshoot devices whose functioning you don’t entirely understand. This is weirdness praxis. Let me tell you a story about that.

This week, I bought a Magic keyboard and trackpad for my Macbook Pro, and tried to use them along with an old VGA Dell monitor via an adapter. The peripherals wouldn’t pair correctly (thanks to deferring updates, I’m still running OS X Yosemite, which might be the issue) and the monitor kept flickering on and off. A friend on Twitter recommended I use a boosted HDMI to VGA converter (which uses an additional USB connector for power), which rerouted power from the shields via the Jeffries tubes and solved the flicker issue. The keyboard and trackpad work, but have a few residual weird behaviors (two-finger scroll won’t work on the trackpad for example, and I can’t beam stuff back from away teams). Then there are other bits of weirding: after the bluetooth pairing, my devices show up twice, once as identified entities, and once as ghosts known only by their addresses, like so (I checked; the two numbers correspond to the two devices, so this is 2 devices, not 4, though there is a slight possibility aliens are eavesdropping on earth by piggybacking on the identities of my keyboard and trackpad, and this is some sort of weird deja vu glitch in their penetration strategy, kinda like the deja vu scene with the cat in The Matrix):

I only moved from Windows to Mac about a year ago, and still haven’t truly bothered to invest time in understanding how the thing works, since I do most of my work on a browser and generally don’t believe in solving unlikely-to-be-fatal problems until things actually crash and stop working. My rudimentary Unix knowledge is now more a distant memory than a live skill, which means I have the ability to pull up CLIs and run a few commands that produce bad-ass looking Mr. Robot type results, but don’t actually fix any issues in the “it’s just unix with pretty graphics” troubleshooting mode my geek friends use. My “unix” abstraction has apparently leaked all utility and turned into a theatrical cargo-cult skill. I can’t hack; I can only act like I am hacking well enough to fool people who have never used a CLI.

The result is that my computing environment is something of a weird mystery to me. A whole bunch of “remind me later” threads of deferred learning, so to speak.

Yes, this is me fishing for free tech support. This is how most of us navigate weirdness. By fishing for free tech support of some sort, from people who have experienced more weirdness than we have in a domain.

It isn’t entirely irrational to keep clicking “remind me later” when faced with decisions that involve navigating weirdness. If you’ve ever done any engineering troubleshooting, you know how frustrating it can be. Symptoms are hard to reproduce and hard to interpret when you can produce them. The troubleshooting tree is generally far too complex for systematic “change one thing at a time” discipline, so you tend to switch, with bipolar impatience, between systematic brute-force testing of possibilities and intuitive dives based on speculative diagnoses.

Troubleshooting is a highly uncomfortable process for anyone who likes their ontologies to be walled gardens and their epistemologies to be arenas for displays of theatrical prowess, with no fumbling and groping about. The most annoying feature of troubleshooting is that there is no real way to estimate how long it is going to take. Troubleshooting is a suspension of time, while you go investigate an abstraction leak. You want to get on with your life, not question what life is, every time some weirdness leaks through your defenses.

Speaking of weirdness leaking through your defenses, here’s my favorite example of an abstraction leak: the genesis incident behind the term bug. When Grace Hopper coined the term in its modern sense, she was referring to a case of a literal bug: a moth that got caught in the Harvard Mark II electromechanical computer, causing a failure. Here’s a picture (public domain) of what should be the most famous moth in the world, taped to a page of the computer’s log book.

The reason this is my favorite example is that it illustrates, with crystal clarity, how weirdness works, and why troubleshooting is hard.

Weirding, as a phenomenon, does not respect the boundaries of your emotional and intellectual mental models and maps. You may not think actual dead moths have a role to play in the functioning of computers, but reality decided otherwise in at least one case.

To work, troubleshooting too should not not respect the boundaries of mental models. There is always a non-zero probability that a true understanding of your weird situation will involve dead moths. If your ways of thinking and feeling behaviors cannot deal with that possibility, they are fundamentally fragile.

Puzzles versus Mysteries

The connection between weirdness and troubleshooting suggests a way to understand the general process of dealing with weirdness as a particular kind of mystery solving.

What kind?

Let me first distinguish mysteries from puzzles. A puzzle, in roughly the sense described by Sarah in Puzzle Theory, is something of a game you play with yourself within a finite universe of discourse that you get to determine. The rules can be logical and rational or weird and silly, but you get to decide.

I recently solved a sudoku for the first time on a flight where I was too distracted to read, and too energized to sleep. It was a strangely relaxing experience. I haven’t been much of a puzzler for decades, but back in college I used to occasionally attempt cryptic crosswords. I think I only once completely solved one, but mostly got somewhere between a quarter and half before I got frustrated.

Sudokus are normal, logical and rational puzzles. Which makes sense since they can be generated by computers. Cryptic crosswords do have rules, but they are weird rules, and even after you learn common ones, clever puzzle makers can confuse you with inventive new clues. This is because cryptic crosswords draw from the fairly open-ended universe of language rules, wordplay patterns, and evolving cultures of linguistic wit.

But either way, puzzles are things created by puzzle designers.

Mysteries, on the other hand, are phenomena that emerge from processes that, to the best of our knowledge, aren’t the result of intelligent design. They cause weirdness to leak into our abstractions as a side-effect of their normal unfolding, not by design. We’re not that important. The universe doesn’t owe us puzzles with satisfying solutions. Your god doesn’t live here.

The universe is not a puzzle, it’s a mystery.

The difference is this: in a puzzle, you make up rules, or have someone make rules up for you to enjoy. The fun of puzzling is the fun of controlled, bounded play. Finite-game fun. In a mystery, it is unclear whether there are rules, and if so, where they come from, and whether troubleshooting weirdness in order to grok them will generate clear outcomes in finite time. If it is fun at all, it is infinite-game fun. I have my doubts about whether fun is the right word, given that weirdness, with its indeterminate emotional texture, dominates the proceedings.

The origin of rules you already grok is just another mystery.

In the discussions around Sarah’s Puzzle Theory post, I was struck by the intuitive association people made between empiricism of some sort and systematic distinctions between “science” and “not-science.” Whether your mental model of empiricism is based on some proceduralized notion of falsification, a specific sensibility, or some sort of practice like mindfulness meditation, doesn’t matter. If your abstractions are capable of leaking, you’re in empiricist mode. You may not choose empiricism, but empiricism always chooses you.

In all cases, empiricism is simply the intellectual and emotional accommodation of the idea that reality may be real. That the fact that certain things don’t go away when you stop believing in them may be significant (Philip K. Dicks out for Harambe!). So the distinction between puzzles and mysteries is empiricism of some sort, in a loose sense that involves engaging the weird.

But not all sorts of mysteries have much to do with weirding. In particular, the classic tradition of ratiocinative detection in popular detective fiction, from Poe through Conan Doyle and Christie, is in fact closer to puzzling than mystery-solving in my sense. The classic cozy mystery (the body in the library of a country manor cut off from the world is the prototypical cozy mystery) is very explicitly set up as a puzzle, and appeals to the same instincts that sudoku and crosswords do.

Less obviously, procedurals too fall within the puzzling tradition: if a systematic “scientific detection method” based on blood spatter analysis and fingerprint databases works out, you’re doing ratiocinative puzzling. “Gritty” procedurals and more “psychological” detective stories (often involving serial killers whose identities you know from page 1) are also often just grown-up puzzles, not real mysteries.

Mysteries in the sense of weirding truly begin in the post-Christie era, though Christie herself saw it coming, in her pushing-the-envelope plots (The Murder of Roger Ackroyd, Murder on the Orient Express, and most significantly, Curtain, Poirot’s last case, which is almost a true mystery).

That said, classic detective fiction often flirts with the weird even if is reluctant to actually go there. More than Poirot (Christie preferred to turn banalities into surprises rather than incorporate the sensational), Sherlock Holmes was an investigator of the seemingly weird (which we can all “singular” in his honor). But it always turned out to be a puzzle rather than a mystery. The resolution to a Holmesian mystery, or any mystery in the ratiocinative tradition, involves restoring a sense of normalcy without actually expanding reality. No abstraction leak, nothing to see here, false alarm, it wasn’t a ghost, just a guy in a mask, move on. An example is a case where Holmes uses strange footprints to determine that an animal involved in a case was a mongoose rather than a dog, and ventures into almost weird hypotheses from there. The reason he can even get that far is that he is an abductive reasoner (rather than a deductive or inductive reasoner, as people often mistakenly assume).

Almost, but not quite. Near-weirdness in a Holmesian mystery is about the improbable in a Bayesian sense, rather than the impossible in a metaphysical sense. As the Holmes-esque character, Dr. House, solver of medical mysteries likes to say, “when you hear hooves, think horses, not zebras.”

But even in the most extreme cases, singularity is not weirdness. It is mere improbability.

The kind of mystery I am talking about truly came into its own with Dirk Gently.

Never Eliminate the Impossible

A clear sign that you’re dealing with weirdness is that the only narratives on offer are fringe, crackpot ones: we’ll explain everything, and balance your emotional books, if you allow for the possibility of aliens in your bluetooth.

In her entertaining essay The Game’s Afoot: Predecessors and Pursuits of a Postmodern Detective Novel (in Theory and Practice of Classic Detective Fiction), Kathleen Belin Owen comments on Douglas Adams’ detective Dirk Gently:

Holmes’ inquiry, purely epistemological, bases itself on empirical data, whereas Dirk Gently, the postmodern detective of Adams’ novel, has to account for ontological uncertainty (such as ghosts and time travel). … What sort of rational philosophy of detection can embrace such elements. Only a guiding principle that contorts the clues of the physical world. Dirk Gently explains, “the only thing which prevented me from seeing the solution was the trifling fact that it was completely impossible. Sherlock Holmes observed ones that once you’ve eliminated the impossible, whatever remains, however improbable, must be the answer. I however, do not like to eliminate the impossible.

In Dirk Gently’s novels, of course, reality expands with cheerful disregard for normalcy, barreling into the future nauseous with complete disregard for sanity. Weird out, and stay out.

I recommend the Gently novels. The line about not eliminating the impossible isn’t just a throwaway hat-tip to Holmes but actually modeled by the character of Dirk Gently in his behaviors and bizarre cognitive leaps. I also recommend the book linked above, and Owen’s essay in particular.

Being good at solving weirdness mysteries is not so much about being good at yet another kind of reasoning. If there’s a fourth pattern of cognition beyond deduction, induction and abduction, it is characterized not so much by how you think but by how you feel.

In particular, when you notice the beginnings of the weirding, do you approach it, expanding the abstraction leak and letting your models collapse, or do you retreat from it, sealing off the leak, and buying yourself a more fragile life extension for your operating mental models?

Do you itch to click reboot now, or do you itch to click remind me later?

Practical concerns of course determine when you actually respond, and how much you can prepare, but the basic approach/retreat response to weirdness is not about practicalities, it is about emotions. In particular, about whether you enjoy the experience of not knowing how to feel, or fear it.

Very meta, I know. Emotions about emotions. Told you I’d evolved spiritually and stuff 😇.

The basic distinction between philosophical conservatives and philosophical liberals might in fact be this: the former instinctively retreat from abstraction leaks, sealing off barbaric new realities at the gate. The latter instinctively approach them, expanding small leaks into full-blown breaches, and rushing forward where more cautious types pull back.

If fools rush in where angels fear to tread, conservatives are the angels, and liberals are the fools. Life is an incessant normalizing for the angelic, an incessant weirding for the fools.

By that measure, I am definitely a liberal, but I wasn’t always one. It took a great deal of crashing for me to turn liberal in this sense.

I suspect all living things, humans included, are philosophical conservatives by their basic nature. The tendency, strongly developed among primates and felines in particular, to follow weirdness gradients — what we call the exploratory instinct — is a relatively late evolutionary development I suspect. One that had to wait for more complex brains to evolve (for humans in particular, this is the theory I frequently cite: variability selection in hominid evolution). But I’d like to be wrong on this one. It would be delightful to learn that worms or slime mold have something like a weirdness-seeking instinct.

Awkwardness and Religion

My favorite new question to ask people, to get at their deep religion so to speak, is about the things they do that make themselves and others feel awkward.

The awkwardness that accompanies the presence of a person in the world is a good measure of their normal level of weirding (heh!). People in various stages of retreat and approach relative to weirdness display different levels of awkwardness.

At one extreme, where you’ve retreated entirely from weirdness, and achieved some sort of 100% sealing of all known abstraction leaks, you are the apotheosis of the non-awkward: a perfected player in some perfect finite game. All updates installed, no updates pending, no reboot needed.

This perfection shows up in how well their thinking/feeling mental models are developed and integrated. Some highly enlightened people have both evolved so symmetrically and harmoniously that their thinking and feeling brains are one and the same.

These people especially struggle with weirdness, since perfection in your current sense of self generally means resistance to reboots and updates. It’s the opposite of a perpetual beta brain. What C. Northocote Parkinson said about the architecture of buildings and organizations applies equally to the architecture of minds:

A mind a δ away from absolute perfection is also a mind an ε of weirdness away from complete collapse: an existence nullifying abstraction leak. Serves you right for clicking “Remind me later” too many times, on too many things.

Here’s the thing: to even want to put your thinking and feeling sides on a path of convergent, harmonious integration and balance is to make assumptions about the nature of the universe and the right way to architect a mind. The assumption is this: evolution lies in the direction of retreat.

It is a kind of spiritual red-pill trap to confuse the caricatured equanimity of empty-mind-like-buddha-flowing-like water with being evolved.

And speaking of red pills, here is another way to understand them: a red-pill is an encapsulated (hehe) instance of “speaking truth to power”. Or more simply, revealing, to believers in a more-wrong model that does not serve their interests, a less-wrong model that serves their interests slightly better, or at least hurts their interests less. An undermining of a false consciousness so to speak, if you like the Marxist way of thinking about these things. The emotional result of being red-pilled is chagrin. Chagrin is in some ways the opposite of feeling weirded out (feeling clued-in perhaps). It is a recognition of the falsity of previously held determinate beliefs, and previously felt clear emotions. You look at old truths and feelings with your back to new truths and feelings, and march backwards into the future, driven to retreat from old certainties by some mix of weakening resentment and growing relief.

The net direction is the same as approaching weirdness, but walking backwards is never quite as effective as walking forwards. To be grey-pilled, by contrast, is to be turned around so weirdness, rather than certainty, is front and center. One reason I no longer really enjoy writing posts in the red-pill mode of The Gervais Principle is that my aesthetic sensibilities have done a 180. I no longer get a kick out of speaking truth to power in that particular way. I get more of a kick out of speaking weirdness to truth. So if you’ve been waiting for more posts in that vein, you’re probably going to disappointed.

Evolving with your face turned towards weirdness, rather than away from it, means accepting that the world is largely unknown-unknown and that encountering more of it is likely to rewire your brain in trivial and profound ways from time to time, through crashes small and big. This means accepting that your presence in the universe will be an awkward one, and stumbling forward into the weirdness anyway, rather than backing into it, focused on fading memories of certainties past.

I get now why the line about comedy and tragedy never felt entirely satisfying to me. It is an assertion about about puzzle universes with no room for weirdness. The mystery universe, the one that requires Dirk Gently-ing to inhabit, has no such closed set of emotional stances for you to pick from and occupy.

In this universe, there is no such thing as the last meditative insight, the last psychotic break, the completely mapped universe of ideas and feelings, or the perfect Ayahuasca cleanse. It’s bugs and crashes all the way down. Speaking weirdness to truth means accepting that there is always a non-zero probability of crashing terminally into insanity, and deciding that that’s an acceptable cost for generative living. Speaking weirdness to truth means choosing life.

Which means there is only one rule of engagement for generative living: You’re not going to know what to feel or what to think at all times.

P. S. You may enjoy reading this dialog I had on Sidewire with Renee DiResta, last week’s guest blogger, on the weirdness of crowds.