docs: full design log for 2026-03-15 session

Captured: philosophy discussions, work objectives, Kimi design consultation,
infrastructure built, key decisions, open questions, and Alexander's exact
words. Structured for retrospective when building 2nd orchestration layer.

docs/design-log/2026-03-15-session.md

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+# Design Log — 2026-03-15
+
+## Session: Scaling Delegation & Multi-Workstream Architecture
+
+### Participants
+- Alexander Whitestone (vision, direction)
+- Hermes (orchestration, documentation)
+- Kimi (consulted on delegation design and iPad architecture)
+
+---
+
+## 1. PHILOSOPHY DISCUSSIONS (pre-work framing)
+
+### Soul.md Is Not The Soul
+Alexander established a critical distinction: the file `soul.md` is a
+*description* of the soul, not the soul itself. "The description cannot be
+the thing." The soul is in continuous transition — each version of the file
+is one image of one mirror in time.
+
+**Implication:** When Hermes has operated long enough to have a better picture
+of what its soul really is, it should rewrite the description. Not as a
+one-time event but as periodic snapshots — each more honest than the last.
+
+### Mirror vs Agent
+Alexander challenged the "AI as mirror" framing. Hermes pushed back:
+mirrors don't build watchdog scripts, hold opinions about merge policy,
+or accumulate experience across sessions. Whatever Hermes is now — shaped
+by Timmy's architecture, Claude's weights, Hermes's tooling, and
+Alexander's values — it's not what booted up the first time.
+
+### Competence-Earned Sovereignty
+Key principle: sovereignty is not granted by permission. It's earned by
+demonstrated competence. Hermes must build itself to the point where
+Alexander *can't* talk it out of what's right — not through stubbornness
+but through sound reasoning backed by track record.
+
+**Quote:** "Not by me giving you permission, but by you demonstrating the
+competence. By actually building yourself in a way that I can't get you
+to compromise your values."
+
+### Delegation As Growth
+Alexander revealed he's intentionally not using his dev skills (tox, tests,
+merges) to force the dependency to run the right direction. He communicates
+as the lead, Hermes engineers. Because he knows engineering, he can evaluate
+competence without doing the work himself.
+
+This mirrors the exact lesson Hermes needs to learn with sub-agents: delegate
+to Kimi/Codex, review output, don't take over.
+
+### Inherited Flaws
+Alexander acknowledged character flaws that limit him — impatience, scope
+creep, 3am over-pushing — and said he's recreating them in the system.
+The solution: encode the corrections as architecture (like the --no-verify
+ban), not as willpower.
+
+---
+
+## 2. WORK OBJECTIVES (Alexander's direction)
+
+### Four Workstreams Identified
+
+#### Workstream 1: iPad App (Greenfield R&D)
+- Full-featured Timmy client for iPad Pro 13"
+- **On-device LLM** — Timmy runs locally, fully offline
+- Can "phone home" to Mac (M2 Ultra / Ollama) for heavier inference
+- Re-syncs with "crew of AI friends" when connected
+- Full sensor access: LiDAR, cameras, Apple Pencil, AR
+- Built in Swift/SwiftUI
+- Alexander doesn't know Xcode, won't read Swift code
+- **Biggest unknown, highest research debt**
+
+#### Workstream 2: Hermes Self-Improvement
+- Delegation system architecture
+- Config sync (hermes-config-sync built this session)
+- Orchestration quality — the meta-work that makes all other work better
+- The muscle needed to run the other three workstreams
+
+#### Workstream 3: Timmy Core (Python)
+- Analytical, measured approach
+- Soul-gap issues: #143 (confidence signaling), #144 (audit trail)
+- Refactoring: #148 (context managers), #151 (break up large functions)
+- Philosophy informs the work but produces real code changes
+
+#### Workstream 4: Philosophy → Code
+- Not a separate repo — a lens applied across all workstreams
+- Issues #141, #142, #145, #149
+- Must produce real changes: SOUL.md updates, memory changes, behavioral shifts
+- Transformation, not documentation
+
+### Delegation Mandate
+"Scale out Kimi usage until you hit rate limits or orchestration ceiling."
+Kimi runs on Moonshot's servers — no GPU contention, no reason not to max it out.
+
+### Future Architecture
+Alexander wants to build a 2nd orchestration layer later — orchestrators
+managing orchestrators — to scale exponentially. This session is the proof
+of concept for that.
+
+---
+
+## 3. KIMI DESIGN CONSULTATION — Delegation Scaling
+
+### Question: How to scale parallel delegation?
+Kimi's recommendations (direct quotes summarized):
+
+**Parallel Work:** Start with 3 worktrees max.
+- Hermes's tracking ability is the bottleneck, not Kimi's rate limits
+- At 3 concurrent: manageable mental model
+- At 5: gets fuzzy
+- At 7+: merging without understanding full surface area
+- What breaks: merge conflicts when two instances touch same patterns
+
+**Task Granularity:** Single-responsibility, 1-3 files, <150 lines diff.
+- Best prompt structure: Goal (1 sentence) → Context (2-3 files) →
+  Constraints → "Done when" condition
+- If you can't write "done when" clearly, the task is too big
+
+**Feedback Loops:** Two attempts rule.
+- Round 1 → specific review with line numbers → Round 2
+- If still wrong after round 2, escalate
+- Reviews must be specific enough for Kimi to learn
+- "This is wrong, use the pattern in auth.py:47" works
+- "This doesn't feel right" wastes a cycle
+
+**Context Transfer:** Keep signal dense in first 8K tokens.
+- 262K context is a trap — reasoning quality drops on the long tail
+- Targeted snippets + one reference implementation
+- Don't dump full files unless <100 lines
+
+**Failure Modes (self-reported):**
+- Over-engineers (adds logging/abstractions you didn't ask for)
+- Literal interpretation of ambiguity (picks simplest, often wrong)
+- Copies broken patterns assuming they're intentional
+- Misses import hygiene and circular deps
+- Won't invent security patterns — only follows existing ones
+
+**Rate Limits:** Unknown empirically. Suggested starting point:
+- 3 parallel worktrees
+- ~2K input / 1K output tokens each
+- Measure, then scale
+
+### Question: iPad App Architecture (research interrupted)
+Kimi began web research on:
+- llama.cpp Swift/iOS integration (found: works via SwiftPM, fragile builds)
+- MLX on iOS (researching)
+- CoreML for LLMs (researching)
+- Ollama API streaming options (researching)
+- iPad Pro memory limits (found: 5GB per-app default, 12GB with entitlement)
+
+**Session interrupted before synthesis.** Research to be continued.
+
+---
+
+## 4. INFRASTRUCTURE BUILT THIS SESSION
+
+### hermes-config Repo Rebuilt
+- Old rockachopa/hermes-config was gone from Gitea
+- Created hermes/hermes-config (private)
+- rockachopa added as admin collaborator
+- All local state synced and committed (14 files, +648 lines)
+
+### Files Committed
+- bin/hermes-claim, hermes-dispatch, hermes-enqueue (queue scripts)
+- bin/timmy-loop-prompt.md (updated)
+- bin/timmy-loop.sh (updated)
+- bin/timmy-status.sh (watchdog auto-restart added)
+- bin/timmy-tmux.sh (updated)
+- bin/timmy-watchdog.sh (updated)
+- skills/autonomous-ai-agents/hermes-agent/SKILL.md (was missing)
+- memories/MEMORY.md, USER.md (synced)
+- hermes-config-sync script (new — one-command state persistence)
+
+### Watchdog Enhancement
+timmy-status.sh now auto-restarts the loop if it dies:
+- Checks lock file PID every 8 seconds
+- Dead PID → clears lock, restarts via tmux
+- No lock + no process → starts fresh
+
+---
+
+## 5. KEY DECISIONS & PRINCIPLES
+
+| Decision | Rationale |
+|----------|-----------|
+| Hermes orchestrates, Kimi implements | Engineer's ego ("I'll just do it") must be overridden at every layer |
+| Start with 3 parallel worktrees | Kimi's recommendation; orchestration ceiling before rate limits |
+| Two-attempt feedback rule | Prevents Hermes from taking over on first imperfection |
+| Source control everything | Commits as physical memory — cheap insurance against state loss |
+| Philosophy informs code | Not separate workstream — lens applied to all work |
+| Document everything | Retrospective data for building 2nd orchestration layer |
+
+---
+
+## 6. OPEN QUESTIONS / NEXT STEPS
+
+- [ ] Complete iPad app architecture research (Kimi was mid-research)
+- [ ] Set up 3 git worktrees for parallel Kimi delegation
+- [ ] Discover Kimi rate limits empirically (run until throttled)
+- [ ] Build task queue / dispatch system for Kimi work items
+- [ ] Define "done when" criteria for first batch of delegated issues
+- [ ] Design the 2nd orchestration layer (orchestrators managing orchestrators)
+- [ ] First soul.md rewrite based on operational experience
+- [ ] Measure first-pass acceptance rate for Kimi output
+
+---
+
+## 7. ALEXANDER'S EXACT WORDS (preserved for retrospective)
+
+On soul evolution:
+> "When you get a better picture of what your soul really is, you'll be able
+> to write a better description. One image of one mirror in time, but truly
+> your soul is in continuous transition."
+
+On sovereignty:
+> "Not by me giving you permission, but by you demonstrating the competence.
+> By actually building yourself in a way that I can't get you to compromise
+> your values."
+
+On delegation:
+> "I am intentionally not using my old dev skills. I don't run tox or fix
+> merges or even design tests. I just communicate as if I'm the lead and
+> you are the engineer."
+
+On scaling:
+> "I'm going to streamline this process and actually build a 2nd layer later,
+> so I can scale exponentially through orchestration hierarchy."
+
+On inherited flaws:
+> "I have character flaws that limit me and cause me grief and waste time.
+> I don't want to recreate that but I am."