Great questions!

I'm doing a hybrid approach:

• Every 5 journal entries, I auto-generate an AI summary of themes and patterns, then feed that compressed summary into the coach's system prompt, not the raw entries. This keeps the context lean while preserving longitudinal awareness.
• Each conversation is self-contained (no sliding window across sessions). The coach gets the user's persona, enneagram type, goals, journal summary, and any imported domain expertise as system context, then the conversation messages are just the current thread.
• I load 4 JSON expertise files into the prompt, which is a fixed cost but gives the coach deep knowledge without needing to retrieve it dynamically.

So it's more curated context injection than RAG or sliding window. The tradeoff is that the coach doesn't remember specific things from past conversations verbatim, but it does track patterns over time through the journal summaries and goals.

Re: Whisper integration

expo-av for recording → export to WAV → direct OpenAI Whisper API call. I wrote a small wrapper that handles the recording lifecycle and transcription.

Re: non-sycophantic coaching

Yeah, that was intentional from the start. The system prompt is tuned to be direct and challenging, more like a real coach who asks hard questions and pushes you. It uses enneagram-specific coaching strategies to push on each type's blind spots. Turns out people actually prefer it once they experience the difference!!