pi-planning-with-files

Persistent file-based planning system for organizing complex multi-step tasks and maintaining context across sessions. Creates three markdown files (task_plan.md, findings.md, progress.md) in your project directory to serve as persistent working memory Includes session recovery via script to sync context after /clear commands and resume interrupted work Enforces structured workflows: plan first, update after each phase, log all errors, and never repeat failed actions Provides templates, helper scripts, and a 3-strike error protocol to prevent silent failures and guide systematic troubleshooting

INSTALLATION
npx skills add https://github.com/othmanadi/planning-with-files --skill pi-planning-with-files
Run in your project or agent environment. Adjust flags if your CLI version differs.

SKILL.md

$2a

If you cannot find the script:

Ask Pi to locate it for you:

Run the session-catchup.py script from the planning-with-files skill

If catchup report shows unsynced context:

  • Run git diff --stat to see actual code changes
  • Read current planning files
  • Update planning files based on catchup + git diff
  • Then proceed with task

Important: Where Files Go

  • Templates are in templates/ inside this skill
  • Your planning files go in your project directory

Location

What Goes There

Skill directory

Templates, scripts, reference docs

Your project directory

task_plan.md, findings.md, progress.md

Quick Start

Before ANY complex task:

  • Re-read plan before decisions — Refreshes goals in attention window
  • Update after each phase — Mark complete, log errors

Note: Planning files go in your project root, not the skill installation folder.

The Core Pattern

Context Window = RAM (volatile, limited)

Filesystem = Disk (persistent, unlimited)

→ Anything important gets written to disk.

File Purposes

File

Purpose

When to Update

task_plan.md

Phases, progress, decisions

After each phase

findings.md

Research, discoveries

After ANY discovery

progress.md

Session log, test results

Throughout session

Critical Rules

1. Create Plan First

Never start a complex task without task_plan.md. Non-negotiable.

2. The 2-Action Rule

"After every 2 view/browser/search operations, IMMEDIATELY save key findings to text files."

This prevents visual/multimodal information from being lost.

3. Read Before Decide

Before major decisions, read the plan file. This keeps goals in your attention window.

4. Update After Act

After completing any phase:

  • Mark phase status: in_progresscomplete
  • Log any errors encountered
  • Note files created/modified

5. Log ALL Errors

Every error goes in the plan file. This builds knowledge and prevents repetition.

## Errors Encountered

| Error | Attempt | Resolution |

|-------|---------|------------|

| FileNotFoundError | 1 | Created default config |

| API timeout | 2 | Added retry logic |

6. Never Repeat Failures

if action_failed:

    next_action != same_action

Track what you tried. Mutate the approach.

The 3-Strike Error Protocol

ATTEMPT 1: Diagnose & Fix

  → Read error carefully

  → Identify root cause

  → Apply targeted fix

ATTEMPT 2: Alternative Approach

  → Same error? Try different method

  → Different tool? Different library?

  → NEVER repeat exact same failing action

ATTEMPT 3: Broader Rethink

  → Question assumptions

  → Search for solutions

  → Consider updating the plan

AFTER 3 FAILURES: Escalate to User

  → Explain what you tried

  → Share the specific error

  → Ask for guidance

Read vs Write Decision Matrix

Situation

Action

Reason

Just wrote a file

DON'T read

Content still in context

Viewed image/PDF

Write findings NOW

Multimodal → text before lost

Browser returned data

Write to file

Screenshots don't persist

Starting new phase

Read plan/findings

Re-orient if context stale

Error occurred

Read relevant file

Need current state to fix

Resuming after gap

Read all planning files

Recover state

The 5-Question Reboot Test

If you can answer these, your context management is solid:

Question

Answer Source

Where am I?

Current phase in task_plan.md

Where am I going?

Remaining phases

What's the goal?

Goal statement in plan

What have I learned?

findings.md

What have I done?

progress.md

When to Use This Pattern

Use for:

  • Multi-step tasks (3+ steps)
  • Research tasks
  • Building/creating projects
  • Tasks spanning many tool calls
  • Anything requiring organization

Skip for:

  • Simple questions
  • Single-file edits
  • Quick lookups

Templates

Copy these templates to start:

Scripts

Helper scripts for automation:

  • scripts/init-session.sh — Initialize all planning files
  • scripts/check-complete.sh — Verify all phases complete
  • scripts/session-catchup.py — Recover context from previous session (v2.2.0)

Advanced Topics

Anti-Patterns

Don't

Do Instead

Use TodoWrite for persistence

Create task_plan.md file

State goals once and forget

Re-read plan before decisions

Hide errors and retry silently

Log errors to plan file

Stuff everything in context

Store large content in files

Start executing immediately

Create plan file FIRST

Repeat failed actions

Track attempts, mutate approach

Create files in skill directory

Create files in your project

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