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That’s NOT What ‘Iconoclast’ Means, Kyle
For ‘Kyle’ please read ‘Bill O’Reilly’

‘Lo child,
I assume you’ve noticed, during your ongoing efforts to keep your spam filter from eating this newsletter due to my satirical subject lines — which I truly appreciate — that I’m the kind of person who tends to say stuff people don’t like to hear.
There are a lot of ways to be That Guy, and most of them make you look like an asshole. “The Rebel Truthteller” is a position a lot of people with bad opinions like to take, because it’s got this convenient built-in defense that requires absolutely no data to use: “I’m still right, you just don’t like to hear it, so I get to dismiss your objections, imply that disagreeing with me is a sign of immaturity and lack of intellectual rigor while employing no critical thinking myself, and act superior if you should fail, asserting that my completely unsupported opinion could have prevented your ignoble downfall if you had only listened to me.”
I… try really, really hard not to be That Guy. That Guy sucks. Our government has a lot of That Guy — y’know, the guy who is okay with watching people suffer, because their suffering only proves how right he was in the first place, and suffering is perfectly acceptable so long as it’s somebody else’s fault? That guy likes being smart a lot more than he likes being effective, and I’m not sure how that qualifies a person for anything beyond freshman debate team.
So step one in Not Being That Guy is… when people say you’re being a dick, ‘but it’s the truth’ is not actually a defense. It’s not even on-topic. The person didn’t say, ‘you lied,’ they said, ‘the way you’re expressing yourself is socially unacceptable and makes the people around you unwilling to hear what you have to say.’”
When we know we’re failing to communicate, why would we continually choose to express ourselves in the least effective way? Because it satisfies our emotions in the moment, usually… But does it make us any less likely to experience those insecure emotions that desperately need satisfying in the future? Does being right actually GIVE us anything? Does it do anything for anyone else? Does it make us happy? Does it make us happier than the companionship of other people?