interestingness on demand

the eternal search for the Quality without a Name

Seaport at Sunset, Claude Lorrain, from 1639

'The ship was cheered, the harbour cleared,
Merrily did we drop
Below the kirk, below the hill,
Below the lighthouse top.

It struck me out of the blue recently that it’s my ‘job’ to be interesting.

In some ways this is a blessing and the joy of my life, a childhood dream come true. I used to be so bored as a kid, all the time, and I would seek out interestingness however I could, in whatever snatches of time and space I could carve out for myself. It felt like a matter of existential concern for me, and I would tolerate all manner of punishments in order to continue pursuing interestingness wherever I could find it. The childhood dream, specifically, was “one day I won’t have to pursue interestingness on the side, one day I will get to do it for a living.”

Now I do. In some subtle, specific ways, it can be kind of cursed, seemingly because I haven’t yet reached a threshold where I have absolute freedom to do whatever I like. It used to be impossible for me to pay the bills with interestingness. Now it’s possible, but challenging.

There are several comics I’ve seen over the years that explore this really well (comic artists are usually suffering from the same problem themselves, so these particular comics tend to be very honest, very real). I can’t seem to find them from a quick search, so I’ll satisfice by recalling them from memory. One begins with “do what you love and you’ll never work a day in your life”, and ends with the character being unemployed and begging on the streets. That’s the “No Money” problem. Another has a kid who loves ice cream, and he ends up being in a dystopian factory environment, tasting hundreds of ice cream flavors, looking miserable as hell. That’s the “Too Much Of A Good Thing problem”, or “the dose makes the poison” problem. He makes money now, but that’s way too much ice cream. The challenge for the serious artist is to oscillate between “No Money” and “Too Much Of A Good Thing” while having a spirit of good cheer (cue the ayylmao meme).

I don’t worry so much about the “No Money” problem anymore – now I have an audience, I have people buying my ebooks, people subscribing to my Substack – but what I do worry about is the “Too Much Of A Good Thing” problem, where I push myself so hard to be interesting that I basically ‘kill the golden goose’. I don’t think I’ve ever been in serious danger of doing that, but this goose has certainly sometimes been exhausted from overwork! From trying too hard to be interesting. Which is funny to look back on, because interestingness is everywhere. Things become less interesting when you try too hard. So it’s my job to try hard but not too hard. Which is a tightrope act.

I could probably write a whole separate thing on the psychology of tryhards. The moment I say that, it hits me that I’m creating more work for myself. It’s far likelier that I’d be able to write a paragraph about the psychology of tryhards, within another post like this one. Creating a new draft titled ‘The Psychology Of Tryhards”, would ironically, be me trying too hard. You see how tricksy it is? Every time I think I have the solution to a problem, I have to be careful, because there’s a decent chance that the solution is actually more of the problem in disguise. So it’s my job to notice when I’m creating problems on purpose, in the form of solutioneering, and then stop doing that. 😂

Actually there’s something interesting in that previous paragraph. Which is me noticing that I often come up with good ideas in the middle of other ideas, which might not be as good. TI’ve noticed this before, and I’ve even written about it years ago:

“Trying to make smart writing is often counter-productive. There’s probably a simple reason for this. Smart writing often happens by accident when you accidentally take clever shortcuts when you’re focused on getting from A to B.

Once you know what smart writing looks like, forget about it. Forget about trying to look or sound smart. It rarely happens when you want to. It happens peripherally when you’re trying very hard to communicate something else.” – visakanv.com/blog/smart-writing/ [2019]

It’s my job to accidentally take clever little shortcuts! It’s my job to do one job and then accidentally do another! It’s my job to come up with something and then say “scratch that, this thing I made while making the other thing, this is the real good stuff!” What a very strange job. I love it. I hate it. I love it again. I can’t think of any job I’d rather have instead. Of course, I look forward to not having a job at all, but there’s still quite a climb ahead of me and I have to find ways to enjoy the process, enjoy the grumbling, enjoy the view at the top, and enjoy going back down, going back up, doing it all over again.

(source tweet)

Or not. I don’t have to do anything at all. I could always lay down and die. That’s also always an option. 😂 A dramatic one, but it IS an option! I think it’s important to remember that.

I have more to say about the shortcuts thing. It’s… easy for me to tell other people what they’re doing wrong. I mean, as a creative, I can see what other creatives are struggling with. It’s more obvious when it’s happening in front of my face, outside of me, than when it’s happening inside of me. Additionally, I feel like writing essays used to be easier (maybe I’m romanticizing the past) when fewer people knew who I was, and my writing felt less consequential. I think this is the “excruciatingly meaningful” part of the ayylmao meme. It’s harder for me to relax and enjoy myself, when it feels like what I’m doing is Consequential and Important. But it’s my job to learn to relax and enjoy myself when it feels like what I’m doing is Consequential and Important. 😂

I’m going in circles a bunch, but I feel emboldened to do this on purpose because I’m remembering a bit in Marshall Mcluhan’s Understanding Media (1964), where he talked about how oral traditions would… here, let me just quote it directly:

“Scholars today are acutely aware of a discrepancy between their way of treating subjects and the subject itself. Scriptural scholars of both the Old and New Testaments frequently say that while their treatment must be linear, the subject is not. The subject treats of the relations between God and man, and between God and the world, and of the relations between man and his neighbor—all these subsist together." The Hebrew and Eastern mode of thought tackles problem and resolution, at the outset of a discussion, in a way typical of oral societies in general. The entire message is then traced and retraced, again and again on the rounds of a concentric spiral with seeming redundacy. One can stop anywhere after the first few sentences and have the full message, if one is willing to “dig” it. – MM

If saying it once was sufficient, I’d do that, but it does seem necessary to go in circles so that readers can see the same ideas repeatedly from different angles. I understand this might give some readers a certain nausea, to which I would say… you probably shouldn’t be reading my Substack, lol. The slogan is “In this house, we surf all the channels at once”. It’s only going to get more disorienting from here.

The Sun came up upon the left,
Out of the sea came he!
And he shone bright, and on the right
Went down into the sea.

wake up your idea

(A joke for the Singaporeans.) I went to bed fairly late last night, about 3am or so, and I slept somewhere between 3 to 4.5 hours, before I woke up, still tired, but fired up with the feeling “I haven’t written yet, I should write something, I want to write something.” I’ve been here before, multiple times over the years. Usually it happens earlier – I go to bed before midnight, and wake up with this feeling at around 3am, when the world around me is still asleep. Sometimes– maybe about 10% of the time– I do some of my best writing in this liminal headspace. But oftentimes it doesn’t work out. And this has been a recurring thing about my life.

I’ve wondered, and I wonder now, is it possible to improve my odds? I think it should be possible, with a bit more discipline, a bit more focus, a bit more realism about the situation. Oftentimes when it doesn’t work out, it’s because I got too cosy, too comfortable, and within 2 hours or so I start getting too sleepy-tired to channel whatever it is that wanted to come through. So if I want to improve my odds of these mid-sleep essays working out, I have to cultivate a sense of urgency, this sense of “look I only have about an hour of good consciousness to work with before it falls apart.” I am always hopeful that “today is the day”. Sometimes it is. Oftentimes it isn’t. Nonetheless, for it to work the few times that it does, I have to remain optimistic.

^ I wrote the above paragraphs at the start of today’s writing session. Then I got “distracted” on Twitter and wrote a couple of good threads that may someday come in handy, that maybe might end up being more valuable and important to me than this particular substack essay. I’ve linked them at the bottom of the post. I am now writing this in anticipation of me crossing the checkered flag on this particular post. Go Visa. Go Visa.

✱

The Quality without a Name

Let’s get back to interestingness. It’s my job to be interesting. What is interestingness? I don’t have a simple answer cached in my mind, which is maybe a good thing. Cached answers have a way of being lifeless, dead, until you find a way to revive them with the right angle, the right tone of voice, the right emphasis, the right embodiment. That itself is an interesting thing, that a string of text can be read in so many different ways, and that some ways are much livelier than others. What is it that makes a reading lively? There seems to be a quality that we might call “aliveness” or “resonance” – what I was getting to in my essay “resonance over coherence”. Christopher Alexander called it “The Quality Without A Name”, which is clever – the idea being that even words like “resonance” or “aliveness” can become crutches. They get covered with the dust of familarity:

(source tweets)

Somewhere in the multiverse, a version of this essay would spend the rest of itself explaining what interestingness is, in the abstract sense. Maybe a decade ago I would have found that deeply interesting. But right now, where I’m at on my current journey, I find that somewhat… juvenile? Sophomoric? And I don’t mean that dismissively. I think those are important stages to work through. But I already went through that phase and I’m not interested(!) in repeating it. I’m more interested in working through my present conditions, figuring out how to make myself comfortable, happy, curious, resonant, alive.

And now the STORM-BLAST came, and he
Was tyrannous and strong:
He struck with his o'ertaking wings,
And chased us south along.

wtf is going on?

One of the things that I’m most interested in right now is figuring out what the fuck is really going on with my Substack. I know that I am capable of writing a tremendous amount. In the right conditions, writing flows out of my fingers faster than I can even think. So when I experience something like “writer’s block”, or what I think for me is would be more evocatively and accurately described as “writer’s logjam” (note that ‘block’ and ‘jam’ mean roughly the same thing, and yet it’s worthwhile for me to use the different word, because of the dust of familiarity), the interesting question is… why? How? What’s going on really?

I often find it tempting, when feeling stuck in some way, to feel that the problem is that I’m not trying hard enough. (Here I’m reminded that someone shared Bukowski’s gravestone with me yesterday, and it said “Don’t try.”) But in practice I think the problem is almost always that I’m pushing at a door marked PULL, and then beating myself up for not pushing hard enough, which makes everything worse. Maybe if we pushed harder the door would budge. And sometimes eventually with a herculean effort, we break the door off its hinges and we think “finally!” and/or “well, that went well.” The problem is misframed. Jam is a sign of internal conflict. John Mayer described it as something like, “the part of you that’s the reader is not loving the part of you that’s the writer”. And writing harder is not going to help the reader love the writer more! I find myself thinking it’s sort of like in a marriage, when one spouse gets increasingly heated about trying to please the other, it makes things worse.

So my current most honest diagnosis of “wtf is going on with my substack” is that I’m internally conflicted, I’m trying to do too many things at once, I’m being too hard on myself, I’m not giving myself enough space to just be natural and say what comes naturally to me. Part of it is that I want to do these really thorough, well-researched pieces, but I don’t think those pieces are going to happen until I get a bunch of these things out of the way. I have to let go of my idea of “well-researched pieces”, and just write whatever feels like its coming, and then I have to trust that because I am the kind of guy that cares about researching things, I will write things that have research in them. It’s so wild that I’ve been writing for 20 years and I still have to work through this. But why did I ever expect otherwise? Where did I inherit those assumptions from? An inquiry for another day…

The challenge, again, is to find the fun in it, moment to moment. (source tweet)

So what? who cares?

Wait, something just clicked for me as I reread all of this. The juvenile-sophomoric approach of explaining interestingness, is to me, inferior to the senior-master approach of demonstrating interestingness. And, holy shit, that is what I am trying to do with my substack!! I AM TRYING TO DEMONSTRATE INTERESTINGNESS! It’s so recursive. It’s so simple. And yet, how many people do it? Really, really do it? Properly? Someone complimented me recently with some variant of “it’s impressive how you’re not boring”, and I responded with “i think this is some mix of, not being able to tolerate boredom much to begin with, and repeatedly asking ‘so what? why is that interesting?’ about everything”. That’s my job. My job is to ask “So what? Why is that interesting?” about everything.

Anybody can do that job somewhat– and I recommend that everyone do it a little bit– but I’ve come to see that the truth is that most people are too busy with their own jobs and lives, so it’s actually good that some of us specialize in it, the same way it’s good that we have professionals in any field. (Personally I do think it’s a little crazy to outsource your sense-making and your meaning-making, but some bakers probably think it’s crazy to outsource making your bread.) I have arranged my life – gotten lucky in the right ways and made the necessary sacrifices – such that I can devote decades of time and energy towards asking and living out this question. So even if I’m not the best in the world at it now, I think I have a good shot at becoming one of the GOATs in say, another 30-40 years. Which isn’t to say that you have to become a GOAT at something to have a good, meaningful life, but I have long been afflicted with the persistent delusion that it might be possible for me to do something truly outstanding with my life, if I’m strategic, rigorous, yadda yadda.

I want to additionally note that “I am trying to demonstrate interestingness”, while useful as an internal compass, is not a particularly great beacon, it is not a great vehicle for itself. (And even as an internal compass, it will eventually accumulate the Dust Of Familiarity, and I will have to find something else again. And that’s the joy of it!) I will have to find some oblique ways to convey it. But now I have a puzzle to fiddle with, and I am often at my happiest when I have a puzzle to fiddle with.

The fair breeze blew, the white foam flew,
The furrow followed free;
We were the first that ever burst
Into that silent sea.

I saw this coming

So, the usual digression-distraction thing happened. The thing that I warned myself to look out for, and “be disciplined” about – always a bit of a bullshit statement tbh, coming from me. But here’s what I think is changing: I’m making my peace with it. This is just who I am and where I’m at in my life right now. It hit me again recently that I was somewhat tormented with perfectionism when I was in my teens and early 20s, but looking back, the overwrought writing that I did at the time was a perfect representation of who I was then. Which is to say, there is a perfection in imperfection!

And there can be a kind of egotistical hubris in being perfectionist. My ego is saying, “I can’t be okay just being who I am, who the hell do I think I am? Who I am is not enough, I need to present an image of myself that is better-than-me, and then ideally try to live up to that, then I will be enough.”

Wew. I think there can be a healthy aspirational form of that, but there can also be an unhealthy escapist form of it, and it can be tricky to walk that tightrope. Here’s one of my favorite riffs from Jim Carrey, who I think has struggled very publicly with walking the tightrope himself, and is sometimes playing the Wise Fool at his peers:

“Thank you. I am two-time Golden Globe winner Jim Carrey. When I go to sleep at night, I'm not just a guy going to sleep. I'm two-time Golden Globe winner Jim Carrey going to some well needed shut-eye. And when I dream, I don't dream any old dream. No sir. I dream of being three-time Golden Globe winning actor Jim Carrey. Because then I would be enough. It would finally be true. And I can stop this terrible search. For what I know ultimately won't fulfill me.” – Jim Carrey, at the 73rd Golden Globe Awards

That’s part of what I’m gesturing at when I say that being interesting is my job. Managing my own psychology is my job. Feeling my feelings is my job. Sometimes I feel more like a performance artist than anything else. I sometimes describe myself as an “internet street busker”, and I think part of the job of a street busker is to bring “good vibes” to the environment that they’re in. And that doesn’t necessarily mean performing Pharrell Williams’ Happy on a loop – (that would have terrible vibes, actually) – it could also be singing wistful songs of woe and longing, and that too can add to the “good vibes”. To the quality of resonance, of aliveness, of truth.

to sea, to sea…

He went like one that hath been stunned,
And is of sense forlorn:
A sadder and a wiser man,
He rose the morrow morn.

Seaport with the Embarkation of the Queen of Sheba, Claude Lorrain, 1648 (source)

I’m reminded of a Somebody Feed Phil episode where they’re in Lisbon, and they’re talking about wistful music, saudade, this melancholic sense of being in a port city, and there are always people coming and going, and someone you love might be someone you never see again. So once again we find ourselves talking about wistful ‘The Quality Without A Name’. And I so off I went looking for paintings of ports, and I found the one that I put in the header of this essay. I couldn’t quite find a Portuguese painter who painted ports that I liked, so I went with a French guy, Claude Lorrain, who was born in the year 1600, or maybe 1604 or 1605, sources differ. Actually, he wasn’t really French, not exactly. He was from Lorraine, like how Leonardo was from Vinci. The concept of Being French hadn’t really been invented yet. Isn’t that interesting? And he spent most of his time in Italy. But of course, Italy hadn’t really been invented yet, either. So he used to be regarded as a painter of “the Roman school”. Both his parents died when he was 12. He got commissioned to do a couple of landscapes for Cardinal Bentivoglio, who was so impressed that he recommended Claude to Pope Urban VIII, and once our boy Claude painted for the Pope, his reputation was secured. And I say to myself, isn’t that interesting? It is, isn’t it? It’s all so interesting.

---

Digressions:

• If you’re wondering about the snippets of poetry throughout the post, they’re all stanzas from Samuel Taylor Coleridge’s Rime of the Ancient Mariner (1834)

• thread about the complexity and challenges of doing what you love

• thread about Christopher Alexander’s Timeless Way of Building [1979]

• thread about how working harder can make things worse

• 2021 thread in replies to friends about what it’s like being a creative feral free agent