Sideways

Shift perspective. Unlock creativity.
(2025)

"You're absolutely right!" In spending time working with Claude Code over the past few months, I've seen this response quite a bit. AI models are trained to follow instructions, but sometimes what it actually takes to make progress on a tough problem is to step outside of your current line of thinking. I built Sideways (usesideways.com) to do just this: Sideways is a remote MCP server that injects lateral thinking prompts into AI conversations and coding sessions.

Consider this exchange:

Me: "Help me fix this. Every draft of this email sounds passive-aggressive."
AI: "You're absolutely right! Let's try a friendlier opening line."

And now I'm wordsmithing. The AI sensed confidence, switched into instruction-following mode, and the conversation narrowed. Sideways aims to widen it back out.

How It Works

Add "use sideways" to that initial prompt, and something very different happens:

  1. Your AI determines the reframe category is most relevant and asks Sideways to randomly select a strategy from that category
  2. Sideways returns this strategy: "Stop. Technical problem or avoided conversation?"
  3. Your AI now applies this strategy to your situation, and asks you this refreshingly honest question: "Is this really an email problem, or are you using email to avoid a conversation you should be having face-to-face?"

The entire interaction happens via the Model Context Protocol—Sideways never sees your code, conversations, or work. Only the category name is transmitted.

The Six Categories

Sideways automatically selects from six strategic approaches based on your context:

  • Reframe - Challenge assumptions and see the problem from a completely different angle
  • Reduce - Simplify and eliminate unnecessary complexity to find the core
  • Expand - Add missing elements, perspectives, and possibilities you haven't considered
  • Disrupt - Break conventions and introduce unconventional approaches
  • Embody - Connect emotionally and authentically to the task at hand
  • Pause - Step back, reflect, and reconsider your current direction

Example Use Cases

Sideways works across both code and creative contexts:

  • Debugging - When you're stuck on a persistent bug, Sideways might prompt you to consider what's NOT changing when the error occurs
  • System Design - Rethinking database schema or API architecture from unexpected angles
  • Refactoring - Finding fresh approaches when your code feels tangled
  • Creative Writing - Breaking through writer's block with unexpected narrative perspectives
  • Research & Analysis - Challenging your assumptions when exploring complex topics

Privacy by Architecture

Sideways is built with privacy as a core principle. The server never receives your code, conversations, or creative work. Only category names are transmitted—everything else stays on your device. This architectural choice ensures your intellectual property and creative process remain entirely private.

Platform Support

Sideways works with any AI tool that supports remote MCP servers, including Claude Code, Cline, Cursor, VS Code with Continue, GitHub Copilot, ChatGPT Desktop, Claude.ai, Perplexity, or wherever you get your AI. Visit usesideways.com for installation instructions specific to your environment.

Credits & Inspiration

Sideways draws inspiration from Brian Eno and Peter Schmidt's "Oblique Strategies" (1975), adapting their approach for the era of AI-assisted ideation and problem solving. The project is built on Cloudflare's platform. The visual design of usesideways.com was shaped by chats with Sideways.