Chief of Staff and Executive Coach app

A personal work-management app built on pi: two personas, a Chief of Staff (operational: tasks, commitments, stakeholders) and an Executive Coach (developmental: getting unstuck, pattern recognition), architecturally distinct with asymmetric visibility (the Coach sees everything; the Chief of Staff sees only what Coach sessions explicitly promote). Must feel like a trusted, competent aide, not a cheerful productivity app; no surveillance, no guilt-tripping; Things 3 is the UX benchmark. Principles: structured state in files with explicit tooling, not model memory; commitment integrity at the moment of change (silent due-date changes get caught); honest records without scoring; activation energy, not awareness, is the bottleneck, so design for the transition from intention to action. As of 1 Oct 2026 task, stakeholder and get-unstuck chat are built, the codebase is a reliable BDD codebase with features taking about an hour, and he would not ship it as a terminal app. Primary motivation is personal utility and exposure, not revenue.

Live: re-check with James before relying on this.

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Design principle from his notes

His October 2025 note "design for moral coherence" (bring actions into line with the values you hold or wish you could hold) reads as a principle for this app; see thread-how-people-change. (https://exitmusic.world/design-can-help-tilt-what-we-do-towards-who-we-want-to-be)

Source: James's notes at exitmusic.world (read 2026-10-26); his own position, disposition stated.

Provenance: James, in conversation with Claude, Sept–Oct 2026 (unverified). Disposition: live.

Related: pi-ecosystem, working-patterns

Part of thread: thread-how-people-change (probably the activation-energy tool; James, 2026-10-11)