What we get wrong about smart

There's this advice that gets repeated everywhere: spend your time with people smarter than you. It's good advice. But it misses something.

I used to walk into every conversation doing this mental calculation. Is this person smarter than me? Do they know more? Will I learn something? Started feeling less like curiosity and more like scorekeeping.

The problem isn't the advice. The problem is how we decide who's "smarter."

Here's what I was actually doing when I'd evaluate someone as "smarter than me":

None of that measures intelligence. That's just pattern matching for credentials and confidence.

Met a founder last year who couldn't articulate a single business framework. Dropped out of college. Talked slowly, like he was thinking through every word. But when he described how his users actually behaved versus how he thought they'd behave? That gap between assumption and reality? He saw it clearer than anyone I'd met.

Was he "smarter than me"? Wrong question.

Stopped asking if someone was smart. Started watching how they handled being wrong.

Some people get new information and just... update. No defense mechanism. No explaining why their previous position still kind of made sense. They just shift.

Others—and these are often the people who seem "smartest" in meetings—will absorb new information and find a way to make it confirm what they already thought.

The pattern that surprised me: the people I learned the most from weren't necessarily the ones who knew the most. They were the ones who could say "huh, that doesn't match what I expected" without their ego getting involved.

"Surround yourself with people smarter than you" assumes intelligence is this fixed thing you can rank. But watch what actually happens:

You're building a product. You talk to an engineer who's written database systems for 15 years. Definitely knows more than you about databases. Conversation is valuable, you learn stuff.

Then you talk to a customer who's never written a line of code. They describe how they're currently solving the problem you're trying to fix. They're using a spreadsheet in a way you didn't know was possible, and it's completely backwards from how you designed your interface.

Who was smarter? The engineer knew more facts. The customer saw a reality you were missing.

The useful question isn't "who's smarter?" It's "what does this person see that I don't?"

Started noticing this pattern in who I wanted to spend time with:

People who ask questions because they want to know the answer. Not because they're leading you somewhere or setting up their point. Genuine confusion is rare. Most people are just waiting to talk.

You can feel the difference. Someone asks "how'd you decide to do it that way?" and you can tell immediately if they're actually curious or if they've already decided you did it wrong.

The people who made me sharper weren't the ones with the most answers. They were the ones whose questions made me realize I didn't understand my own thinking.

Three things changed how I think about who to spend time with:

First, I care less about what someone knows and more about what they notice. Knowledge is easier to transfer than observation skills.

Second, I watch how people react when their model breaks. When reality doesn't match their prediction, do they update the model or explain away the data?

Third, I pay attention to whether someone can think out loud without needing to sound smart. The "I don't know, maybe it's..." conversations end up more useful than the polished takes.

You can fill your calendar with impressive people and learn nothing. Seen this happen.

Founder I know spent a year doing coffee meetings with successful people. VCs, other founders who'd exited, advisors. Every conversation felt productive. Everyone was definitely "smarter than him" by conventional measures.

His company didn't move. All that input just created noise.

He switched strategies. Started talking to three people repeatedly: one customer who used his product daily, one engineer who disagreed with his technical approach, and one founder who was six months behind him in a similar space.

Less impressive roster. Way more useful. The customer kept showing him where the product failed. The engineer kept challenging assumptions. The other founder asked questions that hadn't occurred to him because they were still in the messy early phase he'd forgotten about.

You know what's rare? People who are actually curious about how things work when there's no immediate benefit to them.

Most professional conversations are exchanges. I tell you something useful, you tell me something useful, we both get value. Transactional.

But every so often you meet someone who just... wants to understand. They'll ask follow-up questions about a detail that doesn't matter to them. They're not networking, they're not researching, they're just interested.

Those people make you smarter because they give you space to think without performing.

I stopped trying to only spend time with people "above my level." Started paying more attention to whether someone helps me think better.

That can be someone with way more experience. It can also be someone asking naive questions that reveal I've been sloppy with definitions.

The mix that works: Some people who are ahead on the specific path I'm on. Some people solving adjacent problems. Some people who are smart about completely different domains. Some people who are just really curious.

And at least one person who I'm pretty sure thinks I'm doing everything wrong but is invested enough to keep telling me why.