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Learning to Fail · May 15, 2026

The Danger of Knowing Just Enough

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Aaron Dinin · Learning to Fail

I was at a birthday party for a family friend when someone pulled me aside. She told me, not unkindly but quite firmly, that, as someone with a large online audience, I had a responsibility to speak out about one of the various armed conflicts happening around the world right now. By staying quiet, she argued, I was failing the people caught in the middle of it.

I didn’t say much in response. Partly because a birthday party isn’t really the right venue for that conversation, and partly because I wanted to sit with it before I reacted. But I’ve been thinking about the moment ever since and trying to figure out what kind of failure it might be.

Like most people, when I encounter news about a major geopolitical conflict, I immediately form an opinion. It feels almost involuntary. Within seconds of reading something or watching something, I find myself thinking I know which side is right, what should be done, and what responsible people ought to say about it.

But if I slow down long enough, I quickly realize my opinion is almost entirely a reflection of the last thing I read or watched. And if I read a different article or watch a different video that makes a counter argument, what had originally seemed like the “obvious” answer looks less convincing. And, when this happens enough times, I start to realize that most of my opinions about “what’s going on in the world” are simply borrowed from whoever was speaking to me most recently.

By the way, this isn’t a character flaw or something that’s unique to me. It’s how most of us engage with complex, distant events. We understand them through other people’s framings. We absorb their perspectives, we feel the moral certainty that comes with having a view, and we mistake that certainty for understanding.

But any sense of understanding is absurd. At least, it is for these kinds of large, complex, global events. For example, the armed conflict I was being chastised for not speaking about has a history stretching back a long time. It’s a history that specialists spend entire careers studying and still frequently disagree about. So what makes me think my opinion should have any meaningful validity?

The reason I wanted to share this story is because I wonder if the tension I’ve been feeling around “speaking up” is a tension other people have been grappling with, too. After all, confident wrongness isn’t a neutral act. When we share opinions that are poorly informed, we’re not just parroting what other people want us to believe. We’re helping spread those beliefs in ways that are likely serving agendas we can’t even begin to fully understand.

And again, this isn’t just about global conflicts or the pressure to weigh in publicly on serious events. We do a version of this constantly, at much smaller scales. We form judgments about colleagues after one bad interaction. We decide what a piece of legislation will do based on a headline. We constantly take positions on important arguments after thinking about them for forty-five seconds, and we never question whether that’s really enough.

But conviction is a dangerous feeling. What I’d rather practice — and what I think is genuinely more useful — is curiosity. While conviction asks “Which side is right?” curiosity asks “What would I need to understand to actually have an informed view of this?” And doesn’t that seem like the more responsible approach to big, complex issues?

Conviction performs certainty, but curiosity admits what it doesn’t know. And admitting what you don’t know is, in my experience, one of the most undervalued things a person can do in a world that constantly rewards the appearance of having answers.

A helpful reframing for those moments where failure feels possible.

The next time you feel strong conviction rising about something — a news story, a conflict, an argument you’re in — before you say it out loud or act on it, try sitting with a few questions:

- Where did this opinion actually come from, and when did I form it?

- How much of this is the last thing I read or watched, rather than something I’ve actually worked through?

- What would I need to know to feel genuinely confident here — and do I know it?

- Am I trying to understand this, or am I trying to feel certain about it?

- What’s the thing that would most complicate my position, and have I gone looking for it?

While I realize this pause might feel like paralysis, it’s much more about noticing the difference between having simply arrived at a feeling of certainty versus having actually thought something through.

Reflecting on our experiences is where the most important learning happens.

After you’ve held a strong opinion long enough to see what it led you toward, it’s worth asking:

- How did that view hold up, and what made it stronger or weaker over time?

- Where was I borrowing someone else’s certainty without realizing it?

- Did expressing this opinion help anyone think more clearly, or did it mostly just feel good to say?

- Where was I defending the position instead of interrogating it?

- What would genuine curiosity about this have looked like, and what might I have found?

The discomfort of sitting with a question is almost always better than the comfort of a wrong answer.

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