Sideways

Shift perspective. Unlock creativity.
(2025–)

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 injects lateral thinking prompts into AI conversations and coding sessions, available as an Agent Skill or MCP server for 25+ tools.

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."

The AI sensed confidence, switched into instruction-following mode, and the conversation narrowed to wordsmithing. 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 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. With the Skill installation, everything runs locally on your device—nothing is transmitted. With MCP, only category names are sent to the server; your code, conversations, and creative work never leave your machine. Either way, your intellectual property and creative process remain entirely private.

Platform Support

Sideways works with 25+ tools across two categories:

  • Code Editors - Claude Code, VS Code, Cursor, JetBrains IDEs, Zed, Windsurf, and others
  • AI Assistants - Claude Desktop, ChatGPT, Claude.ai, LM Studio, and more

Two installation approaches are available: Agent Skills run offline and require just one command (npx ai-agent-skills install sideways), while MCP connects to a remote server and enables optional usage analytics. 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 MCP server runs on Cloudflare's platform. The visual design of usesideways.com was shaped by chats with Sideways. The project is open source on GitHub.