Working Hypotheses

Have Wonder

November 2025

I sometimes get asked how to write content for companies,In my case that means exclusively enterprise brands. and one hack I’ve used to explain it is “have wonder.”

One way to get to wonder into what you write is to explain “the making of.” After years in any industry, company, or function, you become inured to the magic of producing whatever you produce. You’ve been around it for too long, so it’s hard to see it as magical.

But to an outsider, it is.

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Any aspect of making something can be interesting to an outsider. Making sets for a broadway play, what it takes to give mice cancer for animal studies, how makeup is formulated. Day-to-day, these things are someone’s job that they get bored with like anyone gets bored. But to someone who doesn’t do that, it’s interesting.

Here are some non-branded examples of “have wonder” writing that have stuck with me over the years:

The “making of” trick works because it plays on two things simultaneously that seemingly conflict, and the tension is memorable.

When you see something done at an exceptionally high level, it inspires awe. Imagine watching a ballet dancer who has trained for twenty five years performing steps exquisitely with a body you could never have, or reading the cover paper in Nature about how a scientist brought a new framework to a field you didn’t know existed, or reading the prose of a writer who brings words together with such precision you have to reread and reread. To behold extraordinary expertise inspire us to greatness. But unless you are still young (or feel young), it also can feel impossible to achieve:

“I could never do that!”

On the other hand, learning how awe-inspiring products (art, writing, technologies, startups) are made is eminently relatable. There’s always weird shortcuts, tricks, mistakes, and quirks. And those feel similar to the weird quirks in our own lives. So we end up relating:

“I could totally do that!”

Which is cool, because we are also in awe of it. For me, I know I will never write prose like David Brooks or Anne Lamott, but I do feel like I could crawl around on the floor compiling scribbles, notes, and papers or teach basic writing in Sunday school to a local community. That’s the trick doing its work.

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To write (or shoot, take, draw) this type of content, you have to be an anthropologist. You just landed on planet startup, and you are trying to figure out how it works. You are watching yourself do what you do.

Once you see something ordinary to you through an outsider’s eyes, the magic creates itself. That’s because in order to explain it, and explain why it’s interesting, you have to give a lot of context. And that context is storytelling. Ben and David, probably two of the best storytellers on the planet right now, do this implicitly. Less than 20% of Acquired episodes are analysis or facts. If they opened an episode with a breakdown of Costco’s financials, it would be neat, but it wouldn’t compel the listener. It’s not nearly as compelling as explaining how something happened.

Personal storytelling as they do it is one way to lay context. Another is explaining technical concepts, but at an approachable level. I’m not an engineer but I want to understand how AI works, I’m not a climate scientist but I want to understand how field data is gathered, I’m not an academic but I want to understand language as if I’m still a college linguistics student.

This type of content is hard to produce at first. It takes technical expertise (mastery) and a sense of what is and isn’t interesting to an outsider. The latter comes with practice.

One helpful thing though: it’s what you know. You are writing about what your company does, with the single twist of an altered perspective. Insider to outsider.

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Some branded examples I like are Cloudflare post-mortems or the famous (and controversial) OKTrends blog from OKCupid circa ~2009.

The tone that pulls the outsider in is wonder. It’s the same tone that makes certain tour guides so compelling: they know that whatever story they are weaving will be interesting to you, and they think it’s interesting too. Their interest propels you and then draws you in.

Just ask anyone who has young children. Wonder is contagious.

And the best part about this type of high-context, have-wonder content is that it perfectly finds your audience.

thanks for reading