Context Curation Skill

Created: Monday, January 19, 2026 Updated: Monday, January 20, 2026 Purpose: Systematic process for managing project file context after retros/planning sessions Status: Experimental

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Overview

Context curation follows the "fractal compression" pattern: each level of summary makes the previous level's raw inputs archivable. Before archiving, fold extractable data into addendums or reference docs.

Trigger phrases:

• "context curation"
• "clean up project files"
• "archive old summaries"
• "what can we remove"

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Compression Hierarchy

Daily summaries → Weekly retros → Monthly retros → Quarterly retros → Yearly retros

After completing...	These can be archived...
Daily summary	Raw conversation logs for that day
Weekly retro	Daily summaries for that week
Monthly retro	Weekly retros for that month
Quarterly retro	Monthly retros for that quarter
Yearly retro	Quarterly retros for that year

Principle: Keep at least one copy at each granularity level.

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Retention Minimums

Keep at least one document at each granularity level:

Level	Minimum to Keep
Daily	1-2 most recent summaries
Weekly	Current week's plan + most recent retro
Monthly	Current month's plan + most recent retro
Quarterly	Current quarter's plan + most recent retro
Yearly	Current year's plan + most recent retro

Principle: Even after compression, maintain the ability to see recent state at each time scale.

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Fold Before Archive

Before archiving daily summaries, extract data that should persist in reference docs.

What to Extract

• Quantitative progress (reps, times, measurements, PRs)
• Protocol changes or discoveries
• Status updates for tracked items
• Confirmed additions (new safe foods, new movements, etc.)

Where to Extract

Addendum files for reference docs that accumulate data:

• Reference-Doc.md

  →

  Reference-Doc-Addendum-YYYY-MM-DD-to-DD.md

• Date range matches the weekly retro period
• Example:

  Training-Log-Addendum-2026-02-16-to-22.md

Direct updates for simple status changes:

• Single value changes can go directly to main doc
• Level progressions, status flips, etc.

Addendum Naming Pattern

{Reference-Doc}-Addendum-YYYY-MM-DD-to-DD.md

Where date range matches the weekly retro being processed.

When Addendums Get Compressed

During weekly curation, fold addendums into their main docs:

1. Review addendum content
2. Integrate into appropriate sections of main doc
3. Update revision date on main doc (e.g.,

   **Updated:** 2026-02-23

   )
4. Save updated doc to project (replaces old version)
5. Archive the processed addendum

Why revision dates matter: When Claude produces an artifact for a reference doc, the revision date makes it clear which version is current. Old version can then be archived/removed from project.

Reference Doc Versioning

Date-in-filename (preferred for periodic revisions):

• Identity-Ecosystem-2025-12.md

  →

  Identity-Ecosystem-2026-03.md

• Old version archived when new version created

Updated-in-content (for incremental updates):

• Keep same filename, update internal

  **Updated:** YYYY-MM-DD

• Works when addendums fold in small changes

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File Categories

Always Keep (Reference Docs)

Documents with ongoing reference value that don't get "rolled up":

• Protocol docs (training plans, nutrition guidelines, recovery routines)
• Framework docs (goal hierarchies, progress tracking systems)
• Context docs (current status, background information)
• Research plans (active investigation threads)

Keep Current Layer

Most recent documents at each temporal scale:

• Current week's plan + most recent weekly retro
• Current month's plan + most recent monthly retro
• 1-2 most recent daily summaries (bridge to current conversation)

Archive Candidates

Documents whose content has been synthesized into higher-level summaries:

• Daily summaries covered by weekly retro (after extraction complete)
• Weekly retros covered by monthly retro
• Past weekly plans (executed, retro complete)
• Past monthly plans (after monthly retro captures outcomes)
• Processed addendums (folded into main docs)
• Old versions of reference docs (replaced by updated version)

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Process

1. Identify Temporal Boundary

What retro just completed?

• Weekly retro → daily summaries for that week can archive
• Monthly retro → weekly retros for that month can archive

2. Review Dailies for Extractable Data

Scan the daily summaries being archived for:

• Quantitative data that belongs in reference docs
• Protocol changes or confirmations
• Progress markers that should persist

3. Extract to Addendums

For each reference doc with extractable data:

• Create or append to addendum file for this week
• Use naming:

  {Reference-Doc}-Addendum-YYYY-MM-DD-to-DD.md

4. Compress Addendums into Main Docs

If any addendums exist from previous weeks:

• Review addendum content
• Integrate into appropriate sections of main doc
• Mark addendum for archiving

5. List Archive Candidates

Quick pass through project files:

• Reference docs: List, confirm keeping, check freshness
• Current layer: Identify most recent at each scale
• Archive candidates: List with reasoning

Format:

**EXTRACT - From this week's dailies:**
- [file]: "[data]" → [addendum file]

**COMPRESS - Addendums ready to fold:**
- [addendum file] (N entries) → [main doc]

**KEEP - Reference Docs:**
- [file] - [brief reason if not obvious]

**KEEP - Current Layer:**
- [file] - [which layer: daily/weekly/monthly]

**REFRESH - May Be Stale:**
- [file] - [why it may need updating]

**ARCHIVE - Folded into [Retro Name]:**
- [file]
- [file]

Refresh triggers (reference docs don't get archived, but they do get stale):

• Time-based: Last updated 30+ days ago
• Event-based: Major milestone, level change, protocol shift
• Content-based: Information contradicts recent summaries/retros

6. User Confirms and Archives

User reacts with:

• ✓ (agree with recommendation)
• ✗ (keep/reconsider specific file)
• Additional context ("also archive X" or "actually keep Y because...")

User then:

• Extracts data to addendums
• Compresses addendums into main docs
• Removes archived files from project

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Edge Cases

Files Not Clearly Covered

If a time period's retro is missing or incomplete:

• Keep the lower-level docs until coverage exists
• Example: Keep Week 11 retro if December monthly doesn't clearly cover that period

Reference Docs That Need Updates

Some "reference" docs get stale:

• Training plans → update as fitness levels change
• Equipment/gear lists → update as needs evolve
• Goal frameworks → update after major milestone shifts

Flag these for refresh rather than archive.

Blended Summaries

When daily summaries span multiple days (due to missed days or combined entries):

• Still archive after weekly retro covers the period
• The blending itself is captured in the retro
• Extract any quantitative data before archiving

No Extractable Data

If dailies have no quantitative/protocol data to extract:

• Skip the extract step
• Proceed directly to archiving
• Retro synthesis is sufficient

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Decision Principles

1. Fold before archive: Extract persistent data before removing source
2. When in doubt, keep: Can always archive later
3. Compression preserves signal: Higher-level synthesis captures what mattered
4. Context is finite: Project files affect conversation quality
5. Recent > old: Prefer keeping recent docs over historical
6. Reference > temporal: Reference docs have longer shelf life than summaries

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Example Session

After Week 8 Retro (Rob's running project):

Claude: Let's do context curation. First, any data to extract before archiving?

**EXTRACT - From this week's dailies:**
- Summary-02-16: "3.1mi at 9:45 pace" → Training-Log-Addendum-2026-02-16-to-22.md
- Summary-02-18: "New stretching routine working well" → Recovery-Protocol-Addendum-2026-02-16-to-22.md
- Summary-02-20: "PR: 5K in 28:32" → Training-Log-Addendum-2026-02-16-to-22.md

**COMPRESS - Addendums ready to fold:**
- Training-Log-Addendum-2026-02-09-to-15.md (4 entries) → Training-Log.md
- Recovery-Protocol-Addendum-2026-02-09-to-15.md (2 entries) → Recovery-Protocol.md

**KEEP - Reference Docs:**
- Training-Plan-5K.md
- Race-Schedule-2026.md
- Training-Log.md
- Recovery-Protocol.md

**KEEP - Current Layer:**
- Weekly-Plan-2026-02-23.md (current)
- Weekly-Retro-2026-02-16.md (just created)
- Summary-02-21.md, Summary-02-22.md (most recent)

**REFRESH - May Be Stale:**
- Training-Plan-5K.md - last updated 6 weeks ago, you've progressed past Week 4 intervals

**ARCHIVE - Folded into Week 8 Retro:**
- Weekly-Plan-2026-02-16.md
- Summary-02-16.md through Summary-02-20.md
- Training-Log-Addendum-2026-02-09-to-15.md (after compression)
- Recovery-Protocol-Addendum-2026-02-09-to-15.md (after compression)

User: Extracted the training data to addendums. Compressed last week's addendums into main docs. Archived the rest.

Claude: Good. Data preserved in reference docs. Context curated.

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Integration Notes

When to trigger:

• After weekly retro + planning complete
• After monthly retro + planning complete
• When context feels bloated / conversation quality degrading

Typical weekly curation flow:

1. Weekly retro (summary-of-summaries)
2. Weekly planning
3. Context curation: a. Extract from dailies → addendums b. Compress addendums → main reference docs c. Archive dailies (now folded into retro) d. Archive processed addendums (now folded into main docs)

Cognitive load:

• Keep it lightweight (quick pass, not deep analysis)
• User makes final call on each file
• Don't force decisions when depleted

Skill dependencies:

• Works alongside retrospective skills (uses their outputs)
• Works alongside planning skills (happens after planning complete)

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"Fold before archive. Keep most recent at each layer."