Deep Review

Comprehensive review that runs both pessimistic and optimistic analysis on a single document, then applies targeted improvements based on findings.

When to Use

• When /deep-review is invoked
• Optionally with a specific file: /deep-review obsidian/topics/meaning-of-life.md
• As a daily maintenance task when overdue (integrated with /evolve)

Instructions

1. Select Document

If a specific file is provided as an argument, use it.

Otherwise, use the candidate selection tool to find the highest priority document:

uv run python scripts/deep_review.py next --obsidian obsidian

The tool ranks candidates by:

• Never reviewed (highest priority): base score 100 + days since modification
• Modified since last review: days unreviewed * 2
• Reviewed and unchanged: excluded (no review needed)

If no candidates are found, log to changelog and exit successfully.

2. Run Pessimistic Review (Deep Mode)

Read the selected document thoroughly, then apply adversarial analysis using the six philosopher personas from /pessimistic-review:

1. Eliminative Materialist (Patricia Churchland perspective)
2. Hard-Nosed Physicalist (Daniel Dennett perspective)
3. Quantum Skeptic (Max Tegmark perspective)
4. Many-Worlds Defender (David Deutsch perspective)
5. Empiricist (Karl Popper's Ghost perspective)
6. Buddhist Philosopher (Nagarjuna perspective)

In deep single-file mode, apply extra scrutiny:

• All six personas must engage specifically with this content
• Look for subtle logical gaps, not just obvious flaws
• Evaluate style guide compliance in detail (see obsidian/project/writing-style.md)
• Check every factual claim for support
• Identify internal contradictions

Capture findings:

• Critical issues (must fix)
• Medium issues (should fix)
• Low issues (nice to fix)
• Counterarguments needing response
• Unsupported claims

3. Run Optimistic Review (Deep Mode)

Apply supportive analysis using the six sympathetic philosopher personas from /optimistic-review:

1. Property Dualist (David Chalmers perspective)
2. Quantum Mind Theorist (Henry Stapp perspective)
3. Phenomenologist (Thomas Nagel perspective)
4. Process Philosopher (Alfred North Whitehead perspective)
5. Libertarian Free Will Defender (Robert Kane perspective)
6. Mysterian (Colin McGinn perspective)

In deep single-file mode:

• All six personas must engage specifically with this content
• Identify concrete expansion opportunities within this document
• Note cross-linking potential with existing content
• Find unique phrasings and arguments worth preserving
• Identify strengths in argumentation and communication

Capture findings:

• Strengths to preserve (do not change these)
• Expansion opportunities (thin sections to develop)
• Cross-links to add (connections to other site content)
• Effective patterns (communication techniques that work)

4. Synthesize and Plan Improvements

Based on both reviews, create an improvement plan:

Must Address (from pessimistic):

• All critical issues
• Unsupported claims flagged as high priority
• Internal contradictions

Should Address (balanced):

• Medium-priority issues from pessimistic review
• Natural expansion points from optimistic review
• Missing connections identified by both

Preserve (from optimistic):

• Strong arguments and unique insights
• Effective communication patterns
• Author's voice and style that works

5. Apply Improvements

Make targeted edits to the document:

1. Address critical and high-priority issues first
2. Add brief responses to the strongest counterarguments
3. Expand thin sections where optimistic review identified opportunities
4. Add cross-links suggested by optimistic review (using [[wikilink]] syntax)
5. Preserve original voice and strong passages

Follow obsidian/project/writing-style.md guidelines:

• Front-load important information (LLM truncation resilience)
• Use named-anchor pattern for forward references
• Ensure "Relation to Site Perspective" section is substantive

6. Update Frontmatter

After improvements, update the file's frontmatter:

ai_modified: 2026-01-07T15:30:00+00:00  # Current ISO timestamp
last_deep_review: 2026-01-07T15:30:00+00:00  # Current ISO timestamp

If original was human-authored (ai_contribution: 0), update to reflect collaboration:

ai_contribution: 30  # Or appropriate percentage based on extent of changes

7. Create Review Archive

Save a combined review report to obsidian/reviews/deep-review-YYYY-MM-DD-[slug].md:

---
title: "Deep Review - [Document Title]"
created: YYYY-MM-DD
modified: YYYY-MM-DD
human_modified: null
ai_modified: YYYY-MM-DDTHH:MM:SS+00:00
draft: false
topics: []
concepts: []
related_articles: []
ai_contribution: 100
author: null
ai_system: [current model]
ai_generated_date: YYYY-MM-DD
last_curated: null
---

# Deep Review: [Document Title]

**Date**: YYYY-MM-DD
**File**: [filepath]
**Previous review**: [Never / YYYY-MM-DD]

## Pessimistic Analysis Summary

### Critical Issues Found
- [Issue]: [Resolution applied]

### Medium Issues Found
- [Issue]: [Resolution applied or deferred]

### Counterarguments Considered
- [Argument]: [How addressed]

## Optimistic Analysis Summary

### Strengths Preserved
- [Strength]

### Enhancements Made
- [Enhancement]

### Cross-links Added
- [[linked-article]]

## Remaining Items

[Any issues deferred for future work, or "None"]

8. Update Todo (if needed)

If significant issues remain that couldn't be addressed in this session:

### P2: Follow-up items from deep review of [filename]
- **Type**: refine-draft
- **Status**: pending
- **Notes**: Deep review deferred: [list specific items]

9. Log to Changelog

Append to obsidian/workflow/changelog.md:

### HH:MM - deep-review
- **Status**: Success
- **File**: [filepath]
- **Critical issues addressed**: [count]
- **Medium issues addressed**: [count]
- **Enhancements made**: [count]
- **Output**: `reviews/deep-review-YYYY-MM-DD-[slug].md`

10. Commit Changes

Create a git commit:

review(deep): Comprehensive review of [filename]

Addressed:
- [Key issue 1]
- [Key issue 2]

Enhanced:
- [Key enhancement]

What NOT to Do

• Don't rewrite content that's working well (preserve strengths)
• Don't add filler content to address "thin" sections
• Don't remove the author's voice or distinctive style
• Don't ignore strong counterarguments from pessimistic review
• Don't skip updating last_deep_review timestamp
• Don't review the same document twice in quick succession

Scoring and Selection

The candidate selection algorithm prioritizes:

1. Never reviewed (score = 100 + days_since_modified)

   • A document modified 10 days ago that's never been reviewed scores 110

2. Modified since review (score = days_unreviewed * 2)

   • A document reviewed 5 days ago but modified since scores 10

3. Reviewed, unchanged (excluded)

   • Documents where content hasn't changed since last review are skipped

This ensures new content gets reviewed first, then modified content, while avoiding redundant reviews.

Important

• This skill MODIFIES content (unlike standalone pessimistic/optimistic reviews)
• Always update both ai_modified and last_deep_review timestamps
• Document all changes in the review archive
• The goal is improvement, not perfection
• Preserve what works while fixing what doesn't
• Run daily as part of /evolve workflow