Dunning-Kruger comes for us all

📅 ⏱️ 13 min read · 2,490 words ✏️ Updated:

I was walking the dog, listening to people have very smart conversations about wars and the US involvement in them, and things that they should do to limit us from getting entangled in foreign wars going forward, and I had an “AHA!” moment where I solved all the problems.

I started imagining all the ways that you could modify the structures of government in the United States to reward diplomacy over violence, intelligence over bluster, thoughtfulness over rashness… And I know this will shock you, but in my head every idea worked. I could SEE it happening, I could imagine that version of the world and it was so peaceful and wonderful and everything worked.

I was riding HIGH on my own supply.

And while that was happening, my brain started making a connection to a “conversation” I had with Claude earlier this week… in that “conversation” I was asking hard questions about how to have a difficult conversation and methodologies to see if I was the problem and if I was what to do about it… and as that continued, every time I asked it to pivot, reconsider, or think about something different it just did it. No questions, no “you’re thinking about this incorrectly” no nothing like that. It got so far down that I finally just called it out that every answer was just a regurgitation of what I had just told it with some flowery language and you’ll never guess what it did. It agreed lol. OF COURSE YOU AGREE. lol. You’re made to agree with me!

And that’s when it clicked, that I was in a Dunning Kruger moment for myself. Everything I could think of went well in my fake government. Of course it would! I only know enough to make dumb suggestions, but I don’t know the details.

In my perfect world my brain was my own sycophant. It wasn’t critically looking at things that I was considering. Like literally I was thinking “what if we folded the department of defense under the Secretary of State, so that we had their over-riding mission as ‘safety through diplomacy’ as a first principle so that violence is a last resort rather than the first one”.

Like read that again and realize just how insane of a prospect it is, but in my head it sounded like unlocking a bank vault. I GOT IT! And I realize that this isn’t treading new ground or anything, but I think it’s important to sometimes get in the mindset of being in a Dunning Kruger moment for your own empathetic reasons.


Imagine being in a room at work, and you’re brought into a meeting where you’re not the expert but someone is nevertheless looking for your perspective.

You might have a similar “aha” moment, and then voice it and see everyone in the room just give you that “oh come on” look. You know the one, it’s a mild eye roll, or a looking down at their hands to avoid eye contact, or a person randomly dropping off camera for a second because you know that they don’t want people to read their face.

And this is where I’m gonna say something you’re probably not expecting me to say… I think it’s actually great when people voice these ideas.

With a caveat.

I love when people voice these ideas WHILE RECOGNIZING THAT THEY MAY BE COMING FROM A PLACE OF IGNORANCE. Now I don’t mean that I need people to be so self aware that they actually see their idea as ignorant. That’s not realistic or fair to people. But what I mean is people being willing to voice ideas and end up being told “no you’re wrong BECAUSE”.

Which is another caveat, because without that “because” you transition this from a conversation to a scolding. If someone is willing to put themselves on the line and give you an idea, and you know it can’t work, it’s not a problem in my head to explain why they’re wrong. It’s a kindness you’re giving to one another. And often times, explaining the limitations of a system gives you ideas for expanding those limitations.


The problem is that it’s risky.

And risky in a variety of ways!

It’s risky to the person asking the question as they’re opening themselves up to criticism. That criticism could even alter the way people perceive you or your work, or they could decide that you’re not as capable as they thought you were. That’s a real and tangible risk that would make a lot of people not want to open up.

It’s also risky to be the person receiving the comment, because what if you’re too dismissive and make someone trying to help feel bad? What if you don’t go hard enough on why their idea won’t work for fear of hurting their feelings and unintentionally make them think it COULD work when you know it can’t? What if the wrong person in the room also hears it and green lights investments?

And what about everyone else in the room – they’re carefully reading your reactions whether you like it or not, and they’re going to calibrate their next time they have an idea based on your reaction!

The whole thing is fraught because we’re all people and we’re all judgmental and we’re all gonna end up doing and saying dumb stuff that we hope isn’t how people see us, but could really affect our relationships.

And the logical person would take all of this in and say “fuck it I’m just gonna sit here and be quiet, doing things in a dumb way is better than the alternative”.

After all, why take such bold risks when the payoff generally is someone just giving you more work? Seriously, what’s the BEST case scenario for what you end up doing with actually asking a question or presenting an idea that’s going to work out? It’s more work, the same pay, and more stress/responsibility.

When you think about it, the risk hits no matter what the outcome. There’s no external benefit, it’s all risk.

The only thing that can possibly be beneficial is INTERNAL benefit. Your own emotional wellbeing.


This is the central tension that I deal with internally and I’m assuming other people feel as well. And I’m sorry if my bosses end up reading this but… I could give a shit if any company I work for is ever “successful”. Companies don’t have emotions, companies aren’t people, companies don’t give a shit about us as people. We’re cogs in a machine, and that’s just the way it is. And honestly… that’s fine. Whatever, you live with the world you’re given, and do the best you can.

But the reason I still care, and the reason I come to work is because even if I don’t care even a tiny bit about company success, I care DEEPLY about the success of the people around me.

Whether it’s right or not, or misguided or not, I see the people I work with first as friends. And you’ll see in movies and TV shows that people in leadership roles will always give you the “you have to be tough they can’t just be your friends” spiel (I’ve been watching a LOT of below deck and you hear it a lot from Captain Lee lol) – and I get what they’re saying but I think it’s different from what I’m saying. They’re saying (fuck it I just mean Captain Lee lol there’s no they it’s just him lol) that your prime responsibility as a leader is to lead and not to make everyone happy. And I don’t see that as being in conflict with friendship.

Friendship isn’t just “I make everyone around me happy” – that’s called sycophancy. And no one needs a sycophant – though if you do there are plenty of AI chatbots happy to help. What a friend is, is someone that makes you better and that you want to spend your time with, and most importantly to me someone you can rely on. Whether that relying on is something physical like helping you move or emotion like being there to listen to your problems, that reliability is huge.

And I see the people I work with as people that can rely on me. And that’s not only going to be to say the easy things but also to say the hard things.

Which doesn’t comply with the risk model I pulled out of my ass earlier in this post. If speaking your mind in places where you’re not an expert puts you at risk, you shouldn’t be incentivized to say the hard things. But if your colleagues aren’t just cogs in a wheel, but rather are friends, people that rely on you and that you in turn rely on, then there’s an incentive toward honesty and healthy conflict.

One of my favorite friendships involves me doing something, my friend telling me all the ways I did it wrong, then me going “shit, I hate you you’re right” then us battling to get to a good outcome (WHATUP ASH). We bicker, we make fun of each other, and we love it. We make each other better. If we were both only focused on not pissing the other off, we couldn’t say anything! And we wouldn’t be getting better. But it’s because we built a human relationship based on the idea that first and foremost we respect one another as a person and value each others opinions. That makes it so that we can then have ridiculous opinions or be flat out wrong and not have it be a “risk”. It’s a part of the process.


As any 76ers fan will tell you, the process isn’t always pretty and doesn’t always result in wins. But the process is what’s important. Outcomes are random. Let’s be honest about that. Sometimes you can do everything right and the outcome is still shitty. Sometimes you do everything wrong and you strike gold.

Process can make it so you are more likely to get better outcomes but in the end you aren’t in control of how things turn out. As I’ve repeated before, my former boss said (probably once lol) and I internalized it forever: if you could predict what’s gonna happen you’d be betting on the stock market and living an easy life on a beach, not working here.

So if you have no control over the outcome, the control you have is over the process.

What does that control look like? It looks like creating human relationships with people that enable them to do the things that you’d need to do to not just achieve success once but rather to create a program that is more likely to result in success in the long term.

You don’t get that from sycophants, you don’t get that from fear, you don’t get that from taking credit for other peoples work. You get that from teams. Which is why I always preach that teams are the ways companies win. You need to have a multi-disciplinary team of people with different view points that can have healthy tensions like the one I described above where you can poke and prod one another and also see where your team is smarter than you and admit it without fear of negative outcomes.

This is why we talk so much about psychological safety. Part of it is of course about the humans feeling good where they are. That’s a given and most of the time it’s what people think is the intended outcome. But that’s just fundamentally wrong. It’s not the outcome, it’s the vehicle to create better outcomes. Because people who are scared do worse work. People who are bored do worse work. People who don’t care do worse work.

So if you create an environment full of fear, or full of pitfalls, or full of busy work… you’re gonna get shitty outcomes.

But if you create an environment of fun, of healthy tension, of people working together on shared goals, of people who respect one another, of people who want to succeed not because of some external factor but because it makes them FEEL good, you’re gonna get really great outcomes.


It’s kinda fun starting a section with “you can’t control the outcomes” then telling you “but here is how you get great outcomes” lol. And I think it’s because I changed the definition of outcomes in the middle of the section – at the beginning we’re talking about BUSINESS outcomes, things like revenue and stuff that the financial analysts care about. Then I changed the definition to what I think outcomes SHOULD be which is about how we build things.

And part of what I like about writing and thinking is this – the world is complicated. It’s full of contradictions. And those contradictions are where the fun really lies. Joy doesn’t exist without sadness. Fear doesn’t exist without security. Pain doesn’t exist without happiness. And you can’t experience what a good team looks like and understand that it’s good unless you’ve been a part of a bad team.

And it’s why I’m so fascinated with Dunning-Kruger because the only way you can know you’re wrong sometimes is to know enough to know you don’t know things! What a weird concept. How do you even unpack it without knowing enough to know what to unpack!

But it’s also why the times I’m in a room and NOT the expert are often the times I have the most fun. I’m probably doing my best work when I’m the expert, but the only reason I can do that good work there, is by experimenting when I’m not the expert. That failure, that loss, that internal scream of “you don’t know what you’re doing” is what enables me to experience the success, wins and feelings of “oh shit I really know what I’m talking about here huh?”

And that internal tension is what you need to drive you. You can work with the external structures to create a world that’s really comfortable and makes you feel good, but it’s not going to feel fulfilling unless it’s ALSO feeding your internal motivation. Unless you know what you believe in, what makes you tick, why you do the things that you do and why they make you feel the way you feel, you’re not going to feel anything beyond the superficial external structures others create for you.

So even though it’s full of risks and fraught with negative outcomes… do something stupid. Suggest something insane. Try out a new way of describing the world.

The worst thing that happens is that you discover it’s not what you care about – and even that learning is important and useful, and is what will lead you to discovering what you DO really care about.