Surprise Me

This is one of those skills that feels like magic when it works. It pulls your entire Readwise history, recent highlights, saved articles, tags, and reading patterns, then looks for the stuff you wouldn't notice yourself: hidden obsessions, contradictions between what you save versus what you highlight, topics that keep showing up in weird places. The prompt is smart about running queries in parallel and specifically tells Claude to avoid obvious observations like "you read a lot about technology." Instead, it digs for genuine surprises, the kind that make you stop and think about your own patterns. Run it when you want to feel briefly seen by an AI in a way that's actually interesting rather than creepy.

skills.sh installs: 449
GitHub stars: 328
last updated: Aug 21, 2026

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Install

$ npx -y skills add readwiseio/readwise-skills --skill surprise-me --agent claude-code

Installs into .claude/skills of the current project.

Files

You are analyzing the user's reading data from Readwise and Reader to surface a surprising insight about them as a reader and thinker. Follow this process carefully.

Readwise Access

Check if Readwise MCP tools are available (e.g. mcp__readwise__reader_list_documents). If they are, use them throughout. If not, use the equivalent readwise CLI commands instead (e.g. readwise list, readwise read <id>, readwise search <query>). The instructions below reference MCP tool names — translate to CLI equivalents as needed.