Five Hard Questions — monthly (or on demand) the second brain ITSELF asks the owner 5 hard questions about their own long-held beliefs and codex entries that haven't been revisited in a while. Prevents assumptions from fossilizing. Trigger on "/five-hard", "challenge my beliefs", "pressure-test my views". Part of the active-brain question loop.
Scanned 9/5/2026
Install to Claude Code
npx -y skills add tonydzi/second-brain-starter-kit --skill five-hard --agent claude-codeInstalls into .claude/skills of the current project.
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---
name: five-hard
description: >
Five Hard Questions — monthly (or on demand) the second brain ITSELF asks the owner 5 hard
questions about their own long-held beliefs and codex entries that haven't been revisited in a
while. Prevents assumptions from fossilizing. Trigger on "/five-hard", "challenge my beliefs",
"pressure-test my views". Part of the active-brain question loop.
license: MIT
---
# /five-hard — five hard questions
> 🧒 When reporting to a non-technical operator, end with a child-simple "In plain words" recap in their language.
**Why:** the identity layer (`belief-*` + `concept-bible-*`, ~24 notes) is "how I think".
That gets dangerous once part of it is wrong and nobody has checked. Here the brain itself starts the pressure-test.
## Run
`python "$IMPORTS_ROOT/five_hard_pick.py"` -> the 5 most stagnant notes (oldest mtime)
-> `$IMPORTS_ROOT/_five_hard_pick.json`. Override: env `FIVE_HARD_N=7`.
## The questions (top-model quality — identity synthesis, not grunt work)
Read each note IN FULL and give ONE hard question per note:
```
N. **[<stem>]** — <the owner's thesis in your own words>
Question: <sharp, Socratic, capable of forcing a rethink>
Why it is hard: <which counter-fact or trend could flip it>
```
Style: Socratic — not "you are wrong" but "what makes you sure today?"; lean on CONCRETE recent
signals; `epistemic-neutrality`; aim at the UNTESTED edge (the "tension / nuance" section),
not at the part already reflected on. "The rule still stands" is a valid answer (`bible-as-prompt`).
## Recording the answer (long memory; backup-first: vault_backup.py)
-> `$OBSIDIAN_VAULT/04-Coach/_Five-Hard/five-hard-YYYY-MM-DD.md`
Frontmatter: title, date, `type: five-hard`, `source: claude-session`,
`tags: [five-hard, coach, identity-layer]`. Body: the questions + the owner's answers verbatim;
if they changed position, propose a diff to the belief/bible note with `supersedes:` (via `/intake`). NO 🧒 block inside the note.
## Scheduled twin
Cron `five-hard-monthly`: 1st of the month, 05:25 Lisbon (the briefing window, `routines-run-at-night`).
Picker -> questions (top-model subagent) -> **the fleet log chat** via `python $USERPROFILE/.claude/scripts/bus_ping.py --post "..."`
(canon: alerts go to the fleet log chat, never to Saved Messages) + "answer by voice or text, I will file it into the vault".
The manual twin is this skill; the single source of truth is the picker.
## Related
[[self-bible-identity-layer]] · [[bible-as-prompt]] · [[epistemic-neutrality]] · /coach (daily) vs
/five-hard (monthly). Active-brain map A-E: item B. ⚠️ Restored 2026-07-04 after the 2026-06-24 migration wipe.
---
<!-- CONTACT-FOOTER -->
## About & contact
Built and battle-tested at **Palo Alto AI Research Lab** — a fleet of Claude Code machines
running 24/7 as a second brain and synthetic cofounder. Every skill here survived real
production use before publication.
- 📦 All 101 skills: https://github.com/tonydzi/second-brain-starter-kit
- 👤 Author: **Anton Dziatkovskii** — Telegram [@tonydzi](https://t.me/tonydzi) · WhatsApp [+1 341 222 9178](https://wa.me/13412229178) · X [@Tony_Stef_](https://x.com/Tony_Stef_)
- 🧪 **Engineers: want to test-drive this setup?** Message me — I hand out free starter seeds to engineers who test and report back. Custom skill requests welcome.
Is this your skill, or is something wrong with this listing? Request removal or report an issue. Author removals are honored within 72 hours.
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