The Load Bearing Question

Why we ask questions that don't matter and how to sit with the ones that do

I’ve been trying to figure out why I veer into asking such mediocre questions, and the more I examine it, the stranger it gets. It’s not that I don’t know how to ask because I clearly have that capacity. Five words with a question mark: “Why did you do that?”

There it is. A question. Except it’s not, really, is it? It’s an accusation disguised with punctuation. So what makes a real question? What is it that’s actually hard about asking?

I’ve spent maybe fifty thousand hours answering things: school assignments, work emails, inquiries about my day. But asking? If I’m honest, I’ve probably spent fifty hours genuinely asking. And I don’t mean “where’s the bathroom” or “how was your weekend”?

I mean asking something that shifts what happens next. A question that makes someone stop, reconsider, reframe. I ask one of those maybe five times a year, and when I do, it’s usually by accident. Then I feel that little spark of “oh, something just changed,” and I have no idea how I did it or how to do it again.

This bothers me more than it should.

Let me show you what I mean. A friend tells me he’s spending every weekend learning Rust. I ask “why Rust?” and we spend twenty minutes talking about memory safety, performance benchmarks, and why garbage collection is actually a problem worth solving.

It’s a perfectly adequate conversation. We’ve answered my question.

But I could have asked “what are you avoiding?” Same situation, different question, and suddenly we might be talking about whether he’s actually interested in systems programming or just tired of shipping features at work, whether learning something hard makes him feel competent again, the ways we use side projects to construct alternate versions of ourselves. The first question kept us on the surface. The second one had a trap door.

I’m starting to believe that questions don’t have inherent difficulty.

They have load-bearing capacity.

Watch what happens. “Are you happy?” That’s a simple question, right? Three words.

But it’s also capable of supporting an entirely different kind of weight depending on who’s asking and what they’re prepared to hear. Asked casually at a party, it gets “yeah, pretty good, you?”

Asked by your spouse at 2 am when neither of you can sleep, it might unravel or rebuild everything. Same question. Different building. And somehow (this is the part I’m still working out) the person asking is choosing the depth before they even speak.

They’re deciding whether they’re building a hut or a cathedral, except they don’t know they’re deciding because the choice is invisible.

I don’t think I always understood this was happening. I thought questions had fixed weights, that “why is the sky blue” was fundamentally simpler than “what is consciousness.”

Everything transitory the knower and the known. — IV. 35

But they’re not different kinds: they’re the same kind wearing different expectations.

A child asks “why is the sky blue?” and gets “because of how light scatters” and moves on. The question carried exactly that much weight and no more.

But you could load the same question differently: why blue and not some other color? Why do we even call it blue when it’s really a thousand shades we’re collapsing into one word? What does it mean that we all agree to call it blue… are we seeing the same thing? Suddenly you’re not talking about rayleigh scattering anymore. You’re somewhere else entirely.

Most of the time I’m choosing the lightweight version without realizing I’m choosing anything.

Someone says “I’m thinking about quitting my job” and I might ask “do you have something else lined up?” when what I maybe should ask is “what would it feel like to stay?” The second question is about truth. But the second one requires me to be ready for an actual answer, and I’m not always ready. So I ask the question I can handle instead of the question that might matter.

We think experience makes you better at questioning. I’ve watched this happen. You work somewhere long enough and you learn to ask “why did we build it this way?” instead of just “how does this work?” You’ve learned that the better question exposes assumptions instead of just extracting information.

But I’ve also noticed something else: the most experienced people often stop asking entirely. Not because they know everything, but because they’ve learned which questions cause friction. I’ve done this. I know which questions make people defensive. Someone says “we should do X” and I can feel there’s a question lurking under that statement—maybe “are we doing X because it’s right or because it’s easy?” But I don’t ask it, because I know certain doors close if you knock. And so I ask a softer version, or I don’t ask at all, and I’ve convinced myself this is sophistication rather than surrender.

But even that’s not quite what I’m trying to get at. There’s something underneath both the asking and the not-asking that I keep bumping into.

Sometimes (and this is what I can’t stop thinking about) sometimes I’ll be in a conversation and I’ll feel this tiny click, like something just came into focus. It’s not curiosity exactly. It’s more like gap-detection. A sense that there’s a question-shaped hole in what’s being said, and if I could just articulate it, everything would shift. Last week a friend was telling me why they deleted all their social media and they kept saying “it was taking too much time” and I kept feeling like there was something underneath that phrase, some question that would make the real thing visible.

But I couldn’t find it.

The words wouldn’t come. I knew the question was there. I could feel its outline, the way you can feel a word on the tip of your tongue. But I couldn’t grab it. And we kept talking around this absence that neither of us could articulate, and eventually the conversation ended and it just felt like I’d missed something important.

That feeling. That moment of sensing the question before you can speak it: that’s the entire game, I think.

Everything else is just technique. But nobody ever taught me to wait for it. They taught me to fill silences, to contribute, to have something ready. They didn’t teach me to sit in the discomfort of not-knowing until I could feel where the real question lives. And most conversations don’t have that gap anyway. Most discussions are just people exchanging information that doesn’t particularly matter, asking questions that don’t particularly land, and I’m part of that pattern. I ask many questions but learn almost nothing from the answers. I’m performing curiosity rather than feeling it.

And the worst part (what really bothers me) is that I’ve been doing this so long I sometimes can’t tell the difference between genuine wondering and social choreography.

I don’t know how to fix this. I know the usual advice: ask “why” five times, be confrontational or be collaborative depending on your style. But that’s all technique, and I’m convinced technique isn’t the problem. The problem is that asking anything real requires me to reveal ignorance, risk defensiveness, predict reactions, and articulate clearly. All in the three seconds before silence gets awkward.

Is this even solvable? Or is this just what it means to be a person trying to navigate social reality: constantly choosing between questions that matter and questions that land, rarely getting both?

Maybe the real question isn’t “how do I get better at asking” but “what am I actually willing to risk to find out something true?”

I’m still sitting with that one. I don’t have an answer yet.

But I’m starting to suspect that walking around with an unresolved question might be exactly what changes what happens next. That the poverty isn’t that we don’t ask enough. the poverty is that we’re so desperate for answers we never let questions breathe. We kill them by resolving them too quickly, by turning them into action items or conversation topics or things we can check off.

What if the point is to stay in the question longer than feels comfortable? To let it sit there, unresolved, doing its work on you even when you can’t see what that work is?

I don’t know. But that’s what I’m trying now. Carrying questions instead of rushing to answer them. Noticing when I feel that click and not immediately trying to force it into words.

It’s uncomfortable. I’m not sure it’s working. But something feels different about it.