Task & Project Management System

Last Updated: 2026-02-16

A practical, markdown-based task management system for solo developers working with AI coding assistants.

Quick Start: Decision Tree

Choose your workflow based on task complexity:

├─ Small task (5-30 min: KB edits, quick fixes, single-file changes)
│  └─ Use: _Now.md → Claude Code direct → _Next_YYYY-MM-DD.md (insights)
│
├─ Medium task (1-4 hours: features, multi-file work, component creation)
│  └─ Use: YYYY-MM-DD_ACTIVE_Description.md → work → move to SESSION
│
└─ Large project (days/weeks: requires planning, multiple phases)
   └─ Use: YYYY-MM-DD_PLAN → phases in active/ → SESSION reports in complete/

Key Principle: Match the overhead to the task size. Don’t over-engineer simple tasks; don’t under-document complex projects.

Folder Structure

_WorkingOn/
├── _Now.md                          # Lightweight dispatcher (5-7 lines)
├── _Next_YYYY-MM-DD_Topic.md        # Session insights & cross-cutting learnings
├── Projects/
│   ├── [project-name]/
│   │   ├── active/                  # YYYY-MM-DD_ACTIVE_*.md
│   │   ├── complete/                # YYYY-MM-DD_SESSION_*.md
│   │   └── plans/                   # YYYY-MM-DD_PLAN_*.md
├── Research/
│   └── [topic]/                     # YYYY-MM-DD_RESEARCH_*.md
└── Tasks/
    ├── active/
    └── complete/

File Naming Convention

Format: YYYY-MM-DD_TYPE_Brief-Description.md

File Types:

SESSION - Completed work reports (goes in complete/)
PLAN - Implementation blueprints (stays in plans/)
ACTIVE - Work in progress (moves from active/ to complete/ when done, renamed to SESSION)
RESEARCH - Learning/findings
NEXT - Cross-cutting insights, workflow improvements, session learnings
TASK - Simple task tracking

Benefits:

✅ Chronological sorting (YYYY-MM-DD prefix)
✅ Clear purpose at a glance (TYPE prefix)
✅ Self-documenting filenames
✅ Scales indefinitely

Workflows by Task Size

Small Tasks (5-30 minutes)

Examples: KB note edits, simple bug fixes, documentation updates, config tweaks

Workflow:

Create/update _Now.md with one-liner pointing to the task
Run /now in Claude Code (or /nowcpw for confirmation + plan)
Work directly with Claude Code—no need for separate ACTIVE files
Commit changes
Document insights (if any) in _Next_YYYY-MM-DD_Topic.md

_Now.md format (lightweight dispatcher):

Project: monorepo - Continue accessibility work
Project: kb-upgrade - Review task management docs
Research: ai-workflow - Explore spec-driven approaches

(Keep it to 5-7 lines max, one per active context)

When to create _Next file:

You discovered a workflow improvement
You learned something worth remembering for future sessions
There are cross-cutting insights that apply to multiple projects
Claude Code hit a limitation you want documented

Don’t create:

❌ PROJECT folders (overkill for quick tasks)
❌ PLAN files (unnecessary overhead)
❌ ACTIVE files (just work directly)

Medium Tasks (1-4 hours)

Examples: Single feature implementation, component work, multi-file refactor, bug investigation with multiple touchpoints

Workflow:

Create Projects/[project-name]/active/YYYY-MM-DD_ACTIVE_Description.md
Spec out the work:
- Objective and why it matters
- Acceptance criteria (checkbox list)
- Files to modify
- Test strategy
Work with Claude Code using /ptr or direct interaction
When complete:
- Move file from active/ to complete/
- Rename from ACTIVE to SESSION
- Add completion metadata (test results, commits, files modified)

Optional: Create a PLAN file first if the approach needs clarification or user approval before implementation.

ACTIVE file template:

# [Project]: [Brief Title]

**Date:** YYYY-MM-DD
**Type:** Feature / Bug Fix / Refactor
**Status:** In Progress

## Objective
[What needs to be done and why]

## Acceptance Criteria
- [ ] Criterion 1
- [ ] Criterion 2
- [ ] Criterion 3

## Files to Modify
- path/to/file.ts - [what changes]
- path/to/file2.ts - [what changes]

## Test Strategy
[How to verify it works]

## Notes
[Working notes, blockers, decisions made during implementation]

Large Projects (days/weeks)

Examples: New site features, major refactors, multi-phase work, architectural changes

Workflow:

Create a PLAN:
- Projects/[project-name]/plans/YYYY-MM-DD_PLAN_Description.md
- Break into phases with time estimates
- Identify critical files
- Define verification strategy
Execute in phases:
- Each phase gets its own ACTIVE file in active/
- Work through phase, commit frequently
- When phase completes, move ACTIVE → complete/ and rename to SESSION
Document completion:
- PLAN file stays in plans/ folder (don’t move it to complete/)
- SESSION reports reference the PLAN
- Final SESSION report summarizes all phases

PLAN file template:

# [Project]: [Brief Title]

**Date:** YYYY-MM-DD
**Scope:** [Estimate of effort, e.g., "3-5 days, 5 phases"]

## Context
[Why this change is needed, problem it solves, background]

## Approach
[High-level strategy, architectural decisions]

## Phases

### Phase 1: [Name] (X hours)
- Task 1
- Task 2
- **Verification:** [How to test this phase]

### Phase 2: [Name] (X hours)
- Task 1
- Task 2
- **Verification:** [How to test this phase]

## Files Affected
- Critical file 1 - [why it's critical]
- Critical file 2 - [why it's critical]

## Success Criteria
[How to verify end-to-end that the project is complete]

## Risks & Mitigations
[What could go wrong, how to handle it]

SESSION report template:

# [Project]: [Brief Title]

**Date:** YYYY-MM-DD
**Status:** ✅ Complete / ⏸️ In Progress / ❌ Blocked

## Summary
[2-3 sentences of what was accomplished]

## Changes Made

**Files Modified:**
- file1.ts - [what changed]
- file2.ts - [what changed]

**Files Created:**
- newfile.ts - [purpose]

**Commits:**
- abc1234 - [commit message]
- def5678 - [commit message]

## Test Results
[Pass/fail rates, metrics, verification steps completed]

## Known Issues
[Any remaining issues or technical debt]

## Next Steps (if applicable)
[What to work on next, or mark as "Complete - no further work needed"]

Decision Framework: When to Use Advanced Tools

Current System (Markdown + Claude Code)

Use for: 90% of your tasks

Strengths:

✅ Zero setup overhead
✅ Version controlled
✅ Tool agnostic (works with any AI assistant)
✅ Human-readable in Obsidian
✅ No plugin dependencies

Ideal for:

All small tasks
Most medium tasks
Large projects with clear requirements

Superpowers Plugin

Use when:

Project needs TDD enforcement (you want test-first discipline)
Multi-phase work requires structured brainstorm → plan → execute
Complex architecture needs Socratic questioning before coding
You want two-stage review (spec compliance + code quality)

Cost:

10-20 min setup overhead per project
Higher token consumption (subagent dispatch + reviews)
Requires plugin installation

Benefit:

Prevents premature “done” (structural enforcement)
Forces test coverage
Breaks down complex features systematically

Skip for:

Small/medium tasks (overkill)
Simple fixes or refactors
Markdown/KB work

Installation:

# In Claude Code session:
/plugin marketplace add obra/superpowers-marketplace
/plugin install superpowers@superpowers-marketplace

Workflow:

/superpowers:brainstorm  # Socratic refinement (skip for simple tasks)
/superpowers:write-plan  # Generate granular TASKS.md
/superpowers:execute-plan  # Execute with TDD + subagent review

Ralph Loop Plugin (Overnight Autonomous Work)

Use when:

Overnight autonomous work would help (e.g., migrate 50 files, bulk refactoring)
Well-defined TASKS.md exists with clear success criteria
Batch operations that don’t need interactive decisions

Cost:

Setup time + headless mode configuration
Risk of waking up to failed state (need good rollback plan)

Benefit:

Wake up to completed work
Good for repetitive, mechanical tasks

Skip for:

Interactive development
Exploratory work
Tasks requiring judgment calls

Installation:

# In Claude Code session:
/plugin install ralph-loop@claude-plugins-official

Usage:

# From terminal (not in CC session):
claude -p "Read TASKS.md and complete all items" \
  --allowedTools "Edit,Read,Bash,Write,Glob,Grep" \
  --max-iterations 50

TASKS.md Pattern (Per-Project Spec)

Use for:

Any project where detailed task tracking helps
Works with or without Superpowers
Good for projects using Ralph Loop
Version-controlled plan that survives /clear

Format: See TASKS_md_Template.md for 3 templates:

Feature Development (Superpowers-compatible)
Overnight Autonomous Run (Ralph Loop)
Simple Checklist (Lightweight)

Integration with _Now/_Next:

_Now.md becomes a lightweight dispatcher:

- Monorepo: see Projects/monorepo/active/YYYY-MM-DD_ACTIVE_*.md
- Python utils: see TASKS.md in utils repo
- KB: reorganize 04_AI/ (working directly)

The _Now/_Next Pattern: Keep or Abandon?

Verdict: KEEP IT (with improvements)

Why keep _Now/_Next:

Temporal state matters - “Now” vs “Next” describes what you’re doing vs what you learned
Works for small tasks - Don’t force every 10-minute task into a PROJECT folder
Cross-project dispatcher - _Now.md is perfect for “what am I working on today?”
Insight capture - _Next files capture workflow improvements, not task completion

Why NOT rename to _ToAI/_FromAI:

❌ Mailbox metaphor fails - you don’t “send” files to AI
❌ Human-hostile - “_ToAI” is confusing when YOU read it later
❌ Forces 1:1 pairing that doesn’t match reality (one _Now spawns many _Next files)

Improvements to _Now/_Next Pattern

1. Date-stamp _Next files:

❌ Old: _Next2.md, _Next3.md
✅ New: _Next_2026-02-14_Testing-Workflow.md

2. Add source reference:

---
Source: _Now.md -- "Research spec-driven workflows"
---

## What Worked
...

## Friction Points
...

## Workflow Improvements
...

3. Keep _Now.md lightweight:

Don’t put task details in _Now.md
Point to project-specific ACTIVE files or TASKS.md
Think of it as “what am I working on?” not “detailed task spec”

4. Use _Next for insights, not logs:

❌ Bad: “Completed tasks 1, 2, 3” (belongs in SESSION report)
✅ Good: “Learned that Superpowers is overkill for markdown work” (cross-cutting insight)

Migration from Old System

If you have old _Next.md or _Next2.md files:

Rename with dates:
- _Next2.md → _Next_YYYY-MM-DD_Topic.md
- Use git log or file timestamp to determine date
Move project-specific Next files:
- If a _Next file is about a specific project, move to Projects/[name]/complete/ and rename to SESSION
Keep cross-cutting insights in root:
- Workflow improvements
- AI tool learnings
- Process refinements

Backward Compatibility

✅ Old _Now.md still works (don’t rename)
✅ Old _Next files are readable (just less organized)
✅ Migrate gradually as you work on each project
✅ No need to retroactively fix everything

Integration with Claude Code Slash Commands

Existing Commands

/now - Review tasks in _Now.md
/ptr - Proceed to implement tasks autonomously, test thoroughly, report when done
/nowcpw - Review _Now.md + confirm understanding + plan approach + wait for approval
/cpw - Confirm + plan (without /now)
/aic - Ask for clarification

Recommended Workflow Patterns

Small task pattern:

1. Update _Now.md with task
2. /now → /ptr
3. Work completes
4. (Optional) Document insights in _Next file

Medium task pattern:

1. Create ACTIVE file with spec
2. /ptr (points Claude to the ACTIVE file)
3. Work completes
4. Move ACTIVE → complete/ and rename to SESSION

Large project pattern:

1. Create PLAN file
2. Get user approval
3. Create ACTIVE file for Phase 1
4. /ptr for Phase 1
5. Move to SESSION, create ACTIVE for Phase 2
6. Repeat until all phases complete

Best Practices

Do’s ✅

Match overhead to task size - Don’t create PROJECT folders for 10-minute tasks
Use templates - Consistent structure aids scanning and review
Date-stamp everything - YYYY-MM-DD prefix enables chronological sorting
Move, don’t copy - When work completes, move ACTIVE → complete/ (don’t duplicate)
Commit frequently - Atomic commits per logical change
Test before reporting done - See CLAUDE.md testing requirements
Document decisions - Future you will thank present you

Don’ts ❌

Don’t over-engineer simple tasks - 5-minute fix doesn’t need a PLAN
Don’t put task details in _Now.md - Keep it lightweight, move details to ACTIVE/TASKS.md
Don’t use paired indices - (_ToAI2 → _FromAI2 forces 1:1 that doesn’t exist)
Don’t leave ACTIVE files in active/ - Move to complete/ when done
Don’t duplicate content - One source of truth per topic
Don’t skip testing - Especially for UI changes (see CLAUDE.md testing workflow)

Success Metrics

Track these after 2-4 weeks of using the new system:

Metric	How to Check	Target
Task completion clarity	How often do you know exactly what was done?	100%
Workflow friction	How often do you struggle to find where to document something?	Rare
Premature “done” incidents	How often does Claude claim done without testing?	<10%
Time to context switch	How long to remember what you were working on?	<2 min
Obsidian navigability	Can you find past work quickly?	Always

Quick Commands

Create new session report:

cd /mnt/d/FSS/KB/Business/_WorkingOn/Projects/[project]/complete
# Create: $(date +%Y-%m-%d)_SESSION_Your-Description.md

List active work:

ls -lt /mnt/d/FSS/KB/Business/_WorkingOn/Projects/*/active/

List completed work (last 10):

ls -lt /mnt/d/FSS/KB/Business/_WorkingOn/Projects/*/complete/ | head -11

Find all ACTIVE files across projects:

find /mnt/d/FSS/KB/Business/_WorkingOn/Projects -name "*_ACTIVE_*.md"

Example: Real-World Usage

Scenario 1: Quick KB Edit (Small Task)

_Now.md:

KB: Fix typo in 04_AI-upgrade/01_Claude Code.md

Workflow:

Open Claude Code
/now → “Fix the typo”
Done, commit
No _Next file needed (trivial change)

Scenario 2: Component Creation (Medium Task)

_Now.md:

Project: monorepo - Add dark mode toggle component

Create ACTIVE file: Projects/monorepo/active/2026-02-16_ACTIVE_Dark-Mode-Toggle.md

Workflow:

Spec out component requirements in ACTIVE file
/ptr → Claude implements
Test (build, E2E, accessibility)
Move to complete/ and rename to SESSION
Document any insights in _Next file if architectural learnings

Scenario 3: Multi-Phase Feature (Large Project)

_Now.md:

Project: monorepo - Accessibility audit and remediation (see PLAN)

Create PLAN file: Projects/monorepo/plans/2026-02-14_PLAN_Accessibility-Audit.md

Phases:

Create 2026-02-14_ACTIVE_Phase-1-Audit.md → work → SESSION
Create 2026-02-15_ACTIVE_Phase-2-Color-Contrast.md → work → SESSION
Create 2026-02-15_ACTIVE_Phase-3-Responsive.md → work → SESSION
Create 2026-02-16_ACTIVE_Phase-4-Testing.md → work → SESSION
Final SESSION report summarizes all phases

PLAN stays in plans/, SESSION reports in complete/

Resources

Key Documents (Archived)

archive/2026-02-16_Quick_Reference.md - Original quick reference (superseded)
archive/2026-02-16_Research_7Frameworks.md - Research on spec-driven frameworks
_Next_2026-02-09_SimpleTaskMgmt_Implementation.md - Historical implementation plan

Templates

TASKS_md_Template.md - Three TASKS.md templates for different use cases

External Resources

Superpowers - Skills framework for Claude Code
Ralph Loop Plugin - Autonomous loops
GSD Framework - Spec-driven development
planning-with-files - TASKS.md pattern

Summary: The Layered Approach

Layer 1: Cross-Project Dispatcher

_Now.md - Lightweight “what am I working on?”

Layer 2: Per-Project Specs

YYYY-MM-DD_ACTIVE_*.md - Medium/large tasks
YYYY-MM-DD_PLAN_*.md - Large projects
TASKS.md (optional) - Detailed task breakdown

Layer 3: Session Outcomes

YYYY-MM-DD_SESSION_*.md - Completion reports
_Next_YYYY-MM-DD_*.md - Cross-cutting insights

Layer 4: Advanced Tools (optional)

Superpowers - For TDD-driven complex features
Ralph Loop - For overnight autonomous work

Bottom Line: Start simple (_Now + direct work), graduate to structured (ACTIVE → SESSION), adopt tools (Superpowers/Ralph) only when specific project justifies the setup cost.

Version: 2.0 Replaces: Previous README.md (2026-02-14), Quick Reference, Research Report Status: Active system as of 2026-02-16