Pester is your AI-powered task enforcer — a to-do list app with attitude.
Built for the person who endlessly ideates, it helps you finish what you start.
Chat with Orrin, your built-in gatekeeper, and get guilt-tripped into actually getting things done.
This isn’t one more to-do app — finish what you start.
In early development.
Initial commit includes project scaffolding, model creation, and database setup. Stay tuned as features like AI task enforcement and chat integration roll out. To follow along, check the Roadmap and Architecture.
| File | Description |
|---|---|
tone-system.md |
Defines Orrin's voice rules and mode behaviors |
orrin-personality.md |
Core identity and philosophical framing |
prompt-templates.md |
GPT prompt system messages by mode |
sample-interactions.md |
Realistic user/Orrin conversations |
ai-chat-guide.md |
How GPT-4o integrates with the app |
architecture.md |
High-level data flow and backend structure |
roadmap.md |
Milestone checklist and build phases |
dev-notes.md |
Implementation decisions and internal log |
- Ruby on Rails 7.1
- PostgreSQL
- Hotwire (Turbo + Stimulus)
- OpenAI GPT-4o API
- HTML / SCSS / JavaScript
- Hosted on Fly.io
- ✅ Manual and GPT-assisted task creation/editing
- 💬 Chat with Orrin, your AI accountability partner — available in Support Mode or Savage Mode
- 🔐 Secure user authentication (email/password)
- 📱 Mobile-first design (PWA)
- 🚫 Task blocking with gatekeeper messages instead of silence
- 🧠 Mode-based tone system that influences Orrin’s responses and behavior
⚠️ Features like deadlines, labels, and prioritization are planned for version 2.
Coming soon: a sneak peek of Orrin’s interface, chat behavior, and real-time task flow.
When it's ready, you'll see it here — with slow claps included.
- July 15: Initial commit. Project setup complete, models created and migrated.
- July 15: SCSS styling framework added (baseline UI setup).
- July 14: Stimulus, Turbo, ActiveCable installed and tested.
- July 14: Created models/controllers for User, Project, Task, Message, and ChatSession.
- July 14: Connected OpenAI API via
OpenAIServicewrapper.
- 👀 Watch this repo to get updates
- ⭐️ Star it if you're curious or want to support the build
- 🛠 Contributions & feedback welcome once core features are live
- 🗨️ Discussions tab will be enabled soon for open feedback
Pester isn’t just a productivity tool — it’s accountability with a personality. Powered by GPT-4o, Orrin adapts to your working style: gently encouraging in Support Mode or blunt and sarcastic in Savage Mode. Either way, you're getting your tasks done — one way or another.
This project is open source under the MIT License.
“You don’t need motivation. You need momentum.” — Orrin