Why planning kills the magic (and how to get it back)

Because breakthrough ideas don’t follow scripts — they start as riffs.

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Dear Friend, Subscriber, and Category Pirate,

Legendary work is often born from giving yourself permission to play.

This week’s Quick Loot is about why it’s important to give yourself (and others) room to experiment. Structured brainstorming and planning? They can’t touch the power of unfiltered exploration.

In Friday’s upcoming mini-book, Permission To Play, we’ll dive into how Category Designers can unleash their best work by embracing what we call the "Permission Paradox." This is when you have the freedom to create, test, and reimagine without fear of failure.

Here’s a short preview:

The Permission Paradox: Legendary Creation Through Play

Innovation rarely happens when you try to “be innovative.”

Take “Sweet Child O’ Mine”, the song that put Guns N’ Roses on the map. It was born not from planning but from Slash and the band just messing around. The freedom to play without judgment let each band member add their unique perspective, which created one of the most iconic songs in rock.

Here’s how the Permission Paradox manifests in business: