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Shitty Maps: A Trojan Horse for Sensemaking
Summary
You’ve made shitty-looking maps before. The rough sketch on a napkin while you were figuring out what you actually thought. The boxes-and-arrows scrawl on a whiteboard that helped the room land somewhere. The marginal doodle that did more work than the deck it sat next to. You probably hid them, or threw them away, or recreated them somewhere fancier or “more acceptable” before showing anyone. This session is about not doing that anymore. Polish is a trap. A finished-looking map either gets waved through—it looks done, so it must be right–or the room balks because they weren’t part of figuring it out. Either way, your map is treated as something fixed, and the thinking stops. The rough version doesn’t have that problem. It stays in motion. It invites the room in. And it’s faster than the “real” tools, which only feel fast because they look legitimate while you’re using them. We’ll dig into why looking shitty works, then practice making rough maps together, and the skill behind the practice that makes the whole thing come together.
Key Insights
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Rough, low-fidelity 's****y maps' reduce social risk and invite collaborative iteration rather than confrontation.
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Visual representations persist in conversation, help point to relationships, and map non-linear concepts better than spoken language.
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Power dynamics and inadequate communication mediums often inhibit people from sharing valuable perspectives in meetings.
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Practicing real-time visual thinking with simple tools like note cards builds muscle memory that helps break conversational stalemates.
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'S****y maps' serve as Trojan horses that sneak clarity into conversations without requiring permission or pretense.
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The posture of presenting rough maps as drafts with invitation to correction reduces ego and resistance in group settings.
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High-fidelity polished designs can shut down discussion by implying settled ideas, whereas rough sketches encourage exploration.
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Visual sense-making is a powerful tool for sense-making, trust-building, and aligning stakeholders beyond verbal explanations.
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AI-generated visualizations can augment conversation but often lack the human vulnerability and fluidity of hand-drawn sketches.
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Breaking down complex problems into smaller chunks visually helps transform overwhelming issues into manageable tasks.
Notable Quotes
"Everything that I make looks s****y. How can I turn this into a benefit?"
"The map on the note card wasn’t calling anyone out. It was providing this shared point of reference."
"If something looks rough, people don’t treat it like a declaration. They treat it like a draft."
"Talking is linear, but systems are non-linear. Visual maps show those relationships that words can’t."
"I didn’t magically have crystal-clear thoughts. I changed the conditions just enough."
"S****y maps are a Trojan horse for sense-making because they’re disarming and inviting."
"The willingness to say, ‘I’m not sure this is right, but is this what we’re talking about?’ That is a s****y map."
"Visual sketching shows human vulnerability in a way that AI cannot."
"High-fidelity maps often squash discussion. Rough maps invite it."
"That pen on paper helps your brain think through ideas faster."
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