Most of the comments seem to divide into two categories: those who have experienced this failure mode, and those attacking the author.
As someone who has learned not to do this, here is what the author is saying. You subconsciously care about yourself more than the person you're talking to. When you want something from them, that's a bad idea.
Those two sentences, if internalized, will cure you of trying to be clever. There's no room for clever when you have to be effective. At least, not manufactured clever.
But the implicit act of comunication is because you want something regarding the person you are talking with, right? Even if it's offering something, you _still_ want them to accept it.
I learned a lot about this through StackOverflow questions. Yes, you want your answer. But you have to be willing to first try very hard by yourself, and to make sure you make it easy for people to answer it to understand you quick and easy.
You can still care about yourself more than the person but at the same time want something from them badly enough that you'll reverse this when you interact with them. It's called sucking up.
I like to think about communication in four tiers from best to worst
In-person: all context clues available
Video: screen acts as barrier; latency inhibits rapport
Voice: all visual information missing
Text: all visual and tonal information missing
The article's advice rings more and more true the further down this list you go
Personally I've noticed I tend towards passive aggressive as "failure mode". Which plays out as "being difficult".
e.g. Authority figure tells me something is X and I think they're wrong. Say as much, but it doesn't stick. End result is I go with X but with lots of resistance. (Not helpful for career)
I'd also venture that what the author describes - online interactions are a rather unique ballgame. IRL I know when I'm the smartest person in the room. Online there is always a real chance that you're arguing against a triple PhD that can school you till the end of time without breaking a sweat, but was just being modest & polite.
There once was a documentary about a small group of British intellectuals (who also happened to be musical virtuosos) in which one of them asserted that the decision boundary between clever and stupid can have arbitrarily small width.
Without more context, this feels like vaguebooking: it seems like it's aimed at a particular person or type of person, but it leaves me guessing at the target. Maybe that means it's me. I wish there were some examples so I knew what kind of clever the author had in mind.
Examples would help, but there's a clue in what he suggests as an alternative: "be polite and to the point". I think any type of cleverness that's indirect or could be perceived as impolite is the kind of cleverness he's talking about.
It probably has something to do with the on-going saga of his relationship with the "Sad Puppies" crowd, though I think the Sad Puppies didn't actually form until years later. And yeah, I wouldn't be surprised if it were an oblique response to something someone tweeted at him.
Getting more specific than that would probably require doing some Twitter archaeology, and I doubt that would be a particularly edifying enterprise. As entertainment options go, watching Scalzi get into minor spats with people who don't like leftist SF/F figures is right up there with reading YouTube comments.
Sometimes I make jokes that go over the recipient's head (almost never directed at them); it makes them feel a bit dumb and either makes me look like a jerk or poor at communicating.
I've tried to pay a lot more to context (what do I know about the person whom I'm talking to? what are their interests? what do they probably know about, and what not?), but it's still a work in progress.
In the meantime, most of my jokes, puns, or wit will get cut.
Yeah, I'm having a similar problem, I don't really understand what this is referring to. I can make guesses, but no way to know if I've hit the right thing.
While I agree that the failure mode of being clever can be asshole, I really don't think that's the default failure mode most of the time. I wish he had provided some examples so I could have a clearer grasp on exactly what he means by clever and asshole.
I feel like the advice should be more like, "If you're going to be clever, make sure it's the right tone for the audience, and that the failure mode of your joke isn't asshole".
You're never going to know that for sure, the more important part is that if you're going to try being clever make sure it can't be misinterpreted as you being an asshole.
This fails to differentiate between intention, action, and interpretation. Wanting to stand out from the crowd, being clever, having a clever idea, and being an asshole are all judgements. What is the intention? What actions might address that intention? Privacy in communication is emphasized, but general points like this apply to all communication. References might be missed, so be careful with them especially the first time.
What seems especially odd is that this post is an apparently unintentional example of the failure mode being discussed. Instead of directly talking about the risk of misunderstanding and how to limit that using simplification a bunch of colorful but ultimately distracting discourse keeps the focus on judgements about character and intent and assembling the clever asshole strawman.
This is especially important when dealing with potential clients. Can't risk putting them off and losing that relationship! Wait til you get to know them, go to the bar and have a few drinks first, see if they have the same humor as you, and then let loose and joke around freely. It also helps to not have a negative or dark sense of humor or personality in general. More people have one than not, but they'll also be quicker to turn on you, so the long-term risk is still too high.
Recruiters would do well to read this. Have noticed an uptick in 'clever' outreaches lately. While they don't necessarily cross over into 'asshole', then definitely make me want to avoid a potentially cringey conversation.
As someone who has learned not to do this, here is what the author is saying. You subconsciously care about yourself more than the person you're talking to. When you want something from them, that's a bad idea.
Those two sentences, if internalized, will cure you of trying to be clever. There's no room for clever when you have to be effective. At least, not manufactured clever.