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No. 002Work & Organisations

To understand, you first have to misunderstand.

Tomiwa Ayandele1 min read

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Secondary school students work at computers while a teacher speaks at the front of the room.
A secondary school computer class. Photograph: James Rhoda, via Wikimedia Commons (CC BY-SA 4.0).

I’ve been sitting with this idea for a while now.

We treat confusion like a problem to solve as quickly as possible. In school, in meetings, in our careers, the pressure is always to get it fast. The person who nods along gets rewarded. The person who says “wait, that doesn’t make sense to me yet” gets a look.

So we learn to perform understanding instead of build it.

And that habit follows us everywhere. Into how we work. Into how we build things. Into how we engage with people and ideas that are different from us.

The best product decisions I’ve seen and the worst ones I’ve been part of have one thing in common: the worst ones skipped the confusion. Someone assumed they understood the user early, locked in a direction, and shipped a thing that solved the wrong problem beautifully.

The best ones stayed uncomfortable a little longer. Asked one more question. Sat with the data that didn’t make sense instead of explaining it away.

Understanding isn’t a moment. It’s what’s left after you’ve moved through the misunderstanding honestly.

I think we underestimate this because confusion feels like failure. And most of the environments we operate in, professionally and socially, punish the appearance of not knowing.

But the people I find genuinely sharp? They’re almost always the ones most comfortable saying I might be wrong about this. Not as a performance of humility. Just because they’ve learned not to close the loop too early.

The misunderstanding is the draft. The understanding is the edit.

You can’t skip the draft.

This essay was first published on substack.com.

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