Hook Street Workflow Architecture — Multi-Device + Mildred + Cadence

Generated: 2026-05-06 · Session 26 close
Sam's ask: "Have a workflow, what I do, where I work from, how I work, when I work, schedule it all, and have it shared with Mildred and all that."
Constraint: Sam works in motion. Phone-first capture, voice-dictated. Multi-business. VA at distance.

The 4-device architecture (each device has ONE primary job)

┌──────────────┐  ┌──────────────┐  ┌────────────────┐  ┌──────────────┐
│   📱 PHONE   │  │  🪟 IPAD    │  │ 💻 SURFACE PRO │  │  🖥️ DESKTOP  │
│   iPhone     │  │  mini        │  │ (in car)       │  │  (home)      │
├──────────────┤  ├──────────────┤  ├────────────────┤  ├──────────────┤
│ CAPTURE      │  │ REVIEW       │  │ EXECUTE        │  │ DEEP WORK    │
│              │  │              │  │                │  │              │
│ • Wispr Flow │  │ • Read HTML  │  │ • Claude Code  │  │ • Sheet edits│
│ • Voice memos│  │ • Click      │  │   in cursor    │  │ • Code dev   │
│ • Quick      │  │   sheet/Apps │  │ • Voice dump   │  │ • Heavy reads│
│   captures   │  │   Script links│ │   into Claude  │  │ • Builds     │
│ • Tap-to-do  │  │ • Manual cell│  │ • Real-time    │  │              │
│   PWA actions│  │   edits      │  │   problem-     │  │              │
│ • Outlook    │  │ • Outlook    │  │   solving      │  │              │
│   email read │  │   email read │  │                │  │              │
└──────────────┘  └──────────────┘  └────────────────┘  └──────────────┘
       │                 │                  │                  │
       └─────────────────┴──────────────────┴──────────────────┘
                              │
                    ┌─────────▼──────────┐
                    │  GOOGLE WORKSPACE  │
                    │  (the brain)        │
                    │                    │
                    │  • Sheets (truth)  │
                    │  • Apps Script     │
                    │    (router)        │
                    │  • Drive           │
                    │  • Gmail (interface)│
                    └────────────────────┘

Why 4 devices, not 1

Device-by-device — what each does and doesn't do

📱 Phone (iPhone)

Primary job: CAPTURE + LIGHT TRIGGER

✅ Voice → text via Wispr Flow
✅ Quick captures (drafts to self in Gmail)
✅ Read MIS emails on Outlook iOS
✅ Tap PWA actions (close loop, mark paid)
✅ iOS Shortcuts (Quick Capture, Open OneDrive Folder, Open Sheet)
✅ WhatsApp / iMessage replies
✅ Photo/screenshot capture (proof artifacts)

❌ Don't try to edit big sheets here — too small
❌ Don't try to deep-read 5-section briefings
❌ Don't try to write long emails

🪟 iPad mini (recommended add)

Primary job: REVIEW + MANUAL EDITS

✅ Open command center HTMLs (this is exactly what they're built for)
✅ Click through sheet links → land in Sheets app → edit cells directly
✅ Click through Apps Script links → review code → minor tweaks
✅ Outlook iOS for emails (same as phone but readable)
✅ Read CONTEXT.md / CURRENT_STATE.md from OneDrive
✅ Annotate screenshots with Apple Pencil
✅ Multi-window view (Sheets + email side-by-side)

❌ Don't try Claude Code here — needs keyboard
❌ Don't try heavy multi-step writes — friction adds up

Recommended apps:
- Microsoft OneDrive (auto-sync workspace)
- Google Sheets
- Outlook for iOS (consistent with iPhone)
- Claude.ai mobile (for non-Code conversations)
- (Optional) Working Copy git client

💻 Surface Pro (in car)

Primary job: EXECUTE / SOLVE in real time

✅ Claude Code in Cursor (the actual building)
✅ Voice dump into Claude (problem-solving in motion)
✅ Real-time response to incoming alerts
✅ Quick commit/push from terminal
✅ Open multiple sheets, debug code

❌ Not for relaxed reading — that's iPad
❌ Not for capture — phone is faster

🖥️ Desktop (home, when stationary)

Primary job: DEEP WORK + BUILDS

✅ Multi-monitor sheet editing
✅ Long Claude Code sessions
✅ Architectural reads (this doc, CONTEXT.md, full codebase)
✅ Schwab/Fidelity broker portals (full screens)
✅ OneDrive folder explorer for reorgs

❌ Not where you live — used in blocks

Cadence — when each thing fires

Daily rhythm (current state)

05:30 — wake (or earlier sometimes)
07:00 — Daven Shacharis at amud (through June 2026)
07:30 — async window with Mildred (Tuesdays specifically)
07:55 — BOS Daily Snapshot fires (auto)
07:55 — HOOKSTREET OS Daily Snapshot
09:55 — MIS Morning Brief (when triggers re-enabled)
10:30 — earliest schedulable meetings
14:05 — MIS 2:05 PM Trade Action
15:00 — MIS Power Hour
17:30 — sunset rhythm shifts (mincha/maariv)

Weekly rhythm

Sun 09:00 — BOS Weekly Review fires
Sun 11:26 — Hookstreet OS Operations Summary (the goldmine)
Sun        — Family Weekly Snapshot to Chanie (when WIFE_ENABLED=YES)
Mon-Fri    — operational rhythm above
Fri        — Shabbos prep window blocks afternoon
Sat        — Shabbos (no work)

Monthly rhythm

Day 1     — most autopay hits + tuition
Day 15    — mortgages
Day 25    — HELOC
Around    — credit card minimums spread across days 3-28
Sun closest to month-end — Hookstreet OS Monthly Overview fires

Mildred shared layer — what she sees, what she doesn't

Mildred is in Uganda, ~10 hrs/week, async. Tuesday is her sync window. She runs from email + the Sheets she has access to.

What Mildred CAN see / edit

What Mildred CANNOT see / has guardrails

How the boundary works in v3 architecture

When PWA / new Obligations sheet ships:
- Mildred logs in with role=mildred → frontend filters out: Accounts tab, MIS data, family rows in PaymentLog
- Sam logs in with role=sam → sees everything
- One URL, two views

This is Phase 2 of the dashboard. Phase 1 is Sam-only login per Sam's voice answer.

Schedule + ritual proposal

Monday — ramp

• 08:00 review Sun Operations Summary email
• 08:30 send Mildred her start-of-week Action_Master push
• 10:30+ first meetings
• Afternoon: tactical MIS / BOS work

Tuesday — Mildred sync day (async)

• 07:30 Mildred picks up overnight email (her morning EAT)
• 09:00 Sam reviews her replies, fills any blanks
• All day: STR coordination drives Tue/Wed-related vendor work
• Evening: Sam EOD reply to Mildred for her Wed morning

Wednesday — GO DAY (most output)

• 08:00 Daily Snapshot
• 09:55 MIS Morning
• 14:05 MIS Trade Action
• Most heavy work happens here

Thursday — execute

• Mid-week meetings (Eden, Asher, etc.)
• 14:05 MIS

Friday — wrap before Shabbos

• 12:00 latest hard meetings
• 13:00+ wrap, finalize for week
• 14:30+ Shabbos prep mode
• 17:30 hard stop

Sunday — review + prep

• 07:53 Weekly Review email
• 11:26 Operations Summary email
• Prep Mon Mildred push
• Family weekly cycle (when wife layer enabled)

The end-of-session protocol Sam asked for

Per Sam: "this is where you can go work for the next steps... could be done on iPad mini or on a phone or something easy and viewed and readable and not missed."

Pattern locked

Every Claude Code session ends with:
1. Living MD file at outputs/YYYY-MM-DD_session-N.md — append-only timeline of what we did
2. Command center HTML at outputs/YYYY-MM-DD_HH-MM_command-center_session-N.html — interactive artifact with all links, questions, action checkboxes (mobile-ready)
3. Commit + push workspace + MIS subrepo if changes
4. Tell Sam: local path + commit hash + 1-line "what's open"

Pattern for picking up next session

Sam opens HTML on iPad mini → reads → answers questions in voice → I pick up from "Q1-QN answered" + the commit hash → continue.

The HTML IS the memory bridge between sessions. No re-discovery hours. 30-second context load.

Where everything lives — the multi-device map

What's missing that needs to ship (in order)

1. Hook Street OS PWA deploy — phone/iPad become live tools, not just readers (~1 hr Sam time)
2. Two-way sync POST endpoints — edit-obligation, update-balance, log-payment (~30-60 min next Code session)
3. Obligations v3 migration — new Sheet, CSV imported, Code.gs CONFIG flipped (~30 min, Sam-only manual)
4. MIS Trade_Planner replacement — paste 13 holdings (~10 min Sam) + Apps Script wire (~30 min next MIS session)
5. Daily Draft Scanner deploy — proactive surfacing of Camille-style fell-through-cracks items (~1.5 hr next BOS session)
6. Mildred role-filtered view (Phase 2) — when ready to share dashboard with her (~2 hrs)

After all 6 ship: the workflow Sam asked for is fully alive. Phone captures, iPad reviews, sheets are authoritative, Mildred sees what she should, Claude Code rebuilds + maintains.

What you can do RIGHT NOW with this doc

Read it on iPad. Decide:

1. iPad mini purchase y/n
2. Migrate to Obligations v3 this week y/n
3. PWA deploy this week y/n
4. Phase 2 Mildred role-filtered view — when

Tell me your answers in the next session. The HTML at outputs/2026-05-06_15-40_command-center_session-26.html has more detail. This doc is the strategy layer.