"I told you so"

Being an asshole is not strategic!

There’s something I’ve noticed in the Democratic political discourse lately — especially but not exclusively on Twitter/X, which is in itself maybe problem #1 — that’s driving me up a wall and I want to rant about just a little:

I-told-you-so politics — abbreviated as ITYS — is a fucking scourge.

ITYS could be literally “I told you so,” or perhaps “see? I was right” or “you should’ve listened to me.” ITYS also includes the related sentiment of “now that I’ve convinced you that I’m right, I’m going to make you feel bad for having been wrong before.”

It’s being a sore winner, lacking in grace.

ITYS is smug. It’s self-righteous. It’s shitty, unwelcoming and often deeply cathartic for the person saying it.

I get it.

I understand the impulse to say it to Trump voters who are, in many ways, getting what they voted for — and I get it for intra-party fights where one side of the stupid fight wants to claim dominance over the other.

Personally, I love being right. I often have to self-edit out some variation of “as I’ve been saying for months/years/decades” (or I proactively decide to keep it in and be a little bit of an asshole. I’m working on it!)

Hell, in this very Substack, I literally bragged about being right when I was reflecting on the year since my book came out. I am no paragon of excellence here.

So believe me when I say: I understand why people do it. It’s so so so tempting to gloat — especially in politics, where to be right about what might happen is, in some ways, the whole thing.

Being right is often the foundation of someone’s career in this business — to win is to prove you know what voters want. (Somehow, the inverse is rarely true: Being wrong rarely ever hurts someone’s career for any sustained period of time. Weird...)

But in politics — as in interpersonal relationships — ITYS is counterproductive. It’s ego over efficacy; self over mission. It’s fundamentally bad strategy!¹

When I see someone going hard on ITYS, I don’t think “oh man, I should really listen to them next time.” I think “what a smug asshole.”

I don’t even know what kind of response ITYS is supposed to yield!

“Okay, congrats, you were right, you’re the best, I’m the worst, congrats”? Is that what you want me to say?

ITYS shifts the focus from fixing the problem to assigning credit for having predicted it.

And in politics specifically, it’s self-defeating in a very literal way: To have people finally agree with you is the whole fucking point!

Persuasion is the job. We are here to get people to change their minds and take action accordingly. When someone comes around to your point of view, making them feel bad for not being “right” sooner doesn’t help your cause. It just makes you feel good.

If the goal is to throw a big party, then you can’t be an asshole when someone shows up — even if they’re a little bit late or took a different path to get there. You just let them in.

ITYS is bullying. It may not feel like bullying, because it’s wearing the costume of being correct, but it’s absolutely bullying.

Our candidates have, generally speaking, been modeling this well. The pundits & political class should follow suit.

I’m making this my fall resolution, and maybe you can join me: While I won’t stop trying to be right 😈, I am going to do my best to stop performing being right.

I’m going to win — and I’m going to be gracious as fuck afterwards.

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A request: At some point in the next few weeks, I’m down to do a mailbag/AMA post! I’ll answer whatever questions you’ve got. Leave ‘em in the comments, reply to this email, or DM them to me directly.

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When We’re in Charge is my leadership book for millennials and gen Z trying to do things differently. Pick up a copy in any format you’d like — hardcover, e-book, or audio book (narrated by yours truly) anywhere you get books, including Amazon or Bookshop.org or literally anywhere else. If you have Spotify Premium, you can listen to for free right this very minute. It’ll be out in paperback in September.

1. I have a friend who often notes: Most of my rants at their core are about my frustration that too many people are incompetent or bad at their jobs. Not wrong! I want people to be excellent!