Why I'd Rather Look Stupid Than Stay Quiet

Curiosity killed the cat

It's funny how early we learn phrases that make curiosity sound like something to be careful with. Don't be nosy. Don't ask too many questions. Don't ask something everyone else seems to already understand.

I've never been particularly afraid of asking a question just because I might be the only person in the room who doesn't know the answer. If something doesn't make sense to me, I'd rather ask than pretend I understand it.

That hasn't always meant asking sophisticated questions. Sometimes they're incredibly basic. But I've learned that being willing to admit what you don't know can teach you far more than trying to look like you already have everything figured out.

Asking Is a Skill You Can Practice

Curiosity can sound like a personality trait, something you either have or you don't. I don't think that's entirely true. We're naturally curious when we're young. We ask questions constantly because we haven't learned to be embarrassed by what we don't know yet.

As we get older, the questions can become harder to ask. We become more aware of how we sound, whether a question is too basic, or whether everyone else already seems to know the answer. Curiosity is still there. We just get better at talking ourselves out of acting on it.

That's why I think asking is a skill you can practice. The more comfortable you become saying, “I don't know—can you explain that to me?” the less intimidating it becomes.

Some of my favorite conversations start with something I genuinely don't understand. It might be someone's career, how they built a business, why they made a particular investment, or how they think about risk. I wasn't trying to extract anything from these conversations. I just wanted to learn.

What I Actually Ask

What I Actually Ask

The questions themselves are usually simple. What do you do? How did you end up doing that? What would you do differently if you were starting over?

None of them are particularly clever. That's the point. I've learned that a good question doesn't have to make you sound smart. It just has to come from genuine curiosity. And then you have to actually listen instead of waiting for your turn to talk.

I remember speaking with a woman who had signed a deal with Shark Tank. One piece of advice she shared with me was surprisingly simple: keep pushing, and focus on solving someone's problem. The bigger the problem you solve, the more money you can make.

That conversation stayed with me because it reminded me that valuable advice doesn't always have to be complicated. Sometimes all it takes is being curious enough to start a conversation and open enough to learn from someone else's experience.

People can tell when you're asking with genuine interest instead of an angle. Some of the most valuable things I've learned about careers, businesses, investing, and life in general have started with a simple question I could have chosen not to ask.

The Cost of Staying Quiet

I don't think anyone enjoys looking uninformed. I certainly don't. But I've become comfortable admitting when I don't know something if asking means I get to learn it.

I actually think being willing to look a little stupid can be an advantage. I'd rather look stupid for five minutes and walk away knowing something I didn't know before than stay quiet because I'm worried about how I'll be perceived.

The discomfort disappears quickly. What I learned doesn't.

Staying quiet can feel safer in the moment, but there's a cost to protecting yourself from that discomfort. Every question you choose not to ask is a missed opportunity to learn something new.

Curiosity Beyond Sales

Curiosity isn't useful only in a professional setting. It's a way of moving through life. A new skill, a new interest, a new person, or an unfamiliar idea can all give you a reason to ask another question.

The older I get, the more I realize how much there is that I don't know. I don't see that as a weakness. I think it's what keeps life interesting. There will always be someone who knows something I don't, has experienced something I haven't, or sees something from a perspective I haven't considered.

The questions may get better over time, but I don't ever want to become so concerned with looking like I know the answer that I stop asking them.

I'd still rather look stupid for five minutes than stay curious in silence.