Write of Passage Weekly - Optimize for Surprise

Write of Passage Weekly

​Hey Writers,

Surprise! We’re still here and so are you. Always a pleasure to bring you the best writing advice on the Internet. We hope you feel the same. Don’t stop sending us your thoughts. We count on you to tell us what’s on your mind—as if you need more to do!

July is the year’s midway point. If you’re the annual review type, this is your halfway heads-up. Take a moment and reflect. How’s it going? What’s working? What’s not? How might you micro (or macro) adjust to meet your goals?

Over here, we’re a couple of months away from Cohort 9. The prep is going well. Since we have a larger team now, Cohort 9 will be bonkers good. It’s amazing what David and Will (and the team) accomplished before there were nine of us. Animals!

Last week, we brought you When to Get Feedback? This week, we zoom in on the power of conversations, and how to know when you’ve unearthed an idea worth writing about.

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The Mailbag
​Your writing questions, answered.

“I like the idea of writing from conversation. What’s something important to keep in mind as I hone my practice of doing so?”

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There’s a subtle art to testing ideas in conversation. First off, try not to ramble. When you’re ecstatic about a new idea, it’s natural to unpack the entirety of our thinking in one fell swoop. Not necessary!

Conversations aren’t the place to explore every nuance, counterpoint, backstory, and implication. If you go off on a 12-minute rant, you’ll lose your crowd.

Embrace the dance of conversation. Pick one small part of your idea and put it out there. Observe. Watch their body language as you speak. Notice the questions they have, the associations that come up, and the language they use. Based on their response, you have new information. You see the map of your idea through their eyes, which shapes your next move.

If they’re confused, zoom out. If they bring up something you never considered, probe deeper. If their eyes widen, they let out a gasp, and go “whoa!”—jackpot. You’ve surprised them. You’ve found something worth building your essay around. Write down what you said, exactly how you said it.

Surprise signals that someone’s mental model of the world has changed. This is colloquially known as “getting your mind blown.” It’s more than just learning a new fact. It’s the kind of epiphany that comes deep from left field and breaks your expectations.

Sometimes we grow so familiar with ideas, we stop recognizing the surprise in them. This is why it's powerful to orbit around ideas with friends. Writing from conversation shows you which of your ideas have shape-shifting power.

Optimizing for surprise means cutting out the filler and doubling-down on the parts that defy expectations.

At the macro-level, it means organizing your essay around the most counter-intuitive part of your idea. Can you compress the surprising element into a coined phrase and refer back to it often?

At the micro-level, you should cut out paragraphs that don’t reveal anything new. If you include a “micro-epiphany” every 100 words, your readers will stay engaged and read through to the end.

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Writer's Toolbox
​The best writing about writing on the Internet.

One from us: In Write of Passage, we use an acronym called CRIBS to guide peer-to-peer feedback. This shared language makes it easier to give, receive, and implement feedback. It stands for confusing, repetitive, interesting, boring, and, you guessed it, surprising! When a reader flags something as “interesting” or “surprising” it means that insights are nested in these sections. Identify the dry patches between these highlights, and either compress, cut, or re-write.
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One from an alum: Raza Jafri, a Write of Passage alum and comedian, wrote a piece called “Feedback Mountain.” It shows how writers can learn from the way comedian’s develop jokes. “My inner circle allows me to test fresh ideas, my fellow craftsmen give me the expertise in joke writing, and public audiences provide me with continuous data points.” While comedians optimize their material based on laughter, writers optimize their material based on surprise.

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Thanks for reading. If you have any burning questions about writing online, getting feedback, or Personal Monopolies, send them over! We’ll feature the best ones in future newsletters.

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Write of Passage Weekly brings you the best writing advice on the Internet. Each edition is 100% devoted to helping you improve your writing, find your people, and build your Personal Monopoly. We’ll answer your questions, curate links, share tools, and give you a behind-the-scenes glimpse into Write of Passage. Thanks for having us in your inbox. Happy writing!