Planning (Base Framework)

Core insight: The planning process is the same at any time scale. What changes is the inputs, the time horizon, and the granularity of experiments.

The Core Structure

Every planning session covers:

1. Coming From → Where capacity/state is now
2. Constraints → What's fixed that we plan around
3. Priorities → 2-3 key focuses (max)
4. Experiments → What to test/try/explore
5. Success Levels → What "good enough" looks like (0-3)

Time Scale as Parameter

Scale	Inputs	Horizon	Output
Daily	Yesterday's summary	1 day	Today's focus
Weekly	Weekly retro	7 days	Weekly plan
Monthly	Monthly retro	4 weeks	Monthly plan
Quarterly	Quarterly retro	3 months	Quarterly plan
Yearly	Yearly retro	12 months	Yearly plan

Natural flow: Retro → Planning at same scale. Insights fresh, immediately inform forward planning.

Process

1. Establish Boundaries

# Verify current date
TZ='America/New_York' date '+%A, %B %d, %Y - %I:%M %p %Z'

Confirm the period being planned:

• Daily: "Planning [Date]. Correct?"
• Weekly: "Planning [Start] - [End]. Correct?"
• Monthly: "Planning [Month Year]. Correct?"
• Quarterly: "Planning Q[X] [Year]. Correct?"
• Yearly: "Planning [Year]. Correct?"

2. Load Context

Load inputs appropriate to scale:

• Daily: Yesterday's summary, today's calendar
• Weekly: This week's retro, monthly goals
• Monthly: This month's retro, quarterly goals
• Quarterly: This quarter's retro, yearly goals
• Yearly: This year's retro, multi-year vision

Purpose: Understand current capacity and context before planning.

3. Identify Constraints FIRST ⚠️ CRITICAL

Before suggesting priorities, identify what's fixed:

Ask about:

• Non-negotiables: Deadlines, appointments, obligations (can't move)
• Known drains: High-effort tasks, energy-intensive work (need buffer)
• Timeline pressures: Reverse-engineering from future dates
• Ongoing experiments: Maintain consistency, don't disrupt data

Scale-appropriate questions:

• Daily: "What's on the calendar? Any energy drains today?"
• Weekly: "What commitments this week? Any dense days?"
• Monthly: "Major milestones? Travel? Known capacity constraints?"
• Quarterly: "Key deliverables? Seasonal factors?"
• Yearly: "Major life events? Strategic bets?"

Why this matters: Suggesting priorities that ignore fixed constraints = plan sets user up for failure.

4. Generate Provisional Plan

After constraints identified, create initial artifact.

Filename template:

[Scale]-Plan-[Date-Range].md

Examples:

• Daily-Focus-2025-12-05.md
• Weekly-Plan-2025-12-01-to-07.md
• Monthly-Plan-2025-12.md
• Quarterly-Plan-2025-Q1.md
• Yearly-Plan-2026.md

5. Framework Structure

# [Scale] Plan: [Theme/Focus]

**Period:** [Date range]

---

## Coming From

- [Capacity insight from retro]
- [Major constraints identified]
- [What worked/didn't from previous period]
- [2-3 bullets max, scannable]

---

## This [Period]'s Priorities

Based on constraints and patterns:

1. [Priority 1 - often constraint-driven]
2. [Priority 2 - from "what worked" + goals]
3. [Priority 3 - stretch, optional]

Does this ordering work given [specific constraint]?

---

## Experiments to Try

From retro "What Didn't Work":
- [Experiment 1]
- [Experiment 2]

---

## Success Looks Like

### Level 0: Foundation
*Minimum viable engagement with the [period]*
*What counts as "showed up" given current context*
[Fill conversationally]

### Level 1: Base
[Minimum viable progress given current capacity]

### Level 2: Target
[Good [period] for current capacity]

### Level 3: Reach
[Exceptional but achievable]

**Good enough = Level 0 always counts. Level 1 is solid. Level 2 is great. Level 3 is amazing.**

---

## Notes

[Period-specific context, reminders, meta-observations]

6. Fill Through Conversation

Pattern:

1. Suggest based on constraints + retro data
2. User reacts (confirms, reorders, adds context)
3. Update artifact in real-time
4. Calibrate success levels together

Pacing by section:

• "Coming From" → flows fast (pull from retro)
• "Priorities" → needs depth (constraint-aware suggestions → reactions)
• "Experiments" → semi-automatic (select from retro proposals)
• "Success Levels" → interactive (calibrate to current capacity)

Core principle: Constraints → Suggestions → Reactions → Refinement

7. Save Final Version

Save to: /mnt/user-data/outputs/[filename]

Remind user: "Click 'add to project' to save permanently."

Success Level Framework

Level 0: Foundation

• Always counts
• "I engaged with this at all"
• Protects against all-or-nothing thinking
• Even on hardest days, L0 is achievable

Level 1: Base

• Solid progress given capacity
• Sustainable, repeatable
• Not heroic, just consistent

Level 2: Target

• What a good [period] looks like
• Stretch but realistic
• Builds momentum

Level 3: Reach

• Exceptional outcome
• Everything aligned
• Amazing but not required

Calibration: Levels adapt to current capacity. Level 2 during recovery ≠ Level 2 at full capacity.

Core Principles

2-3 priorities max: More than that diffuses focus.

Constraints first: Understand what's fixed before suggesting what's flexible.

Work with what is: Start from actual capacity, not imagined capacity.

Experiments over commitments: Frame as tests, not obligations. Permission to pivot.

Level 0 always counts: Foundation protects against perfectionism spirals.

Plans are hypotheses: Execution adapts in real-time. Retro captures what actually happened.

Edge Cases

First plan at a scale:

• No retro to pull from
• Start with constraint identification
• Set conservative success levels
• Retro at end will establish patterns

Retro → Planning same session:

• Natural flow if context headroom available
• Check tokens before proceeding
• Benefits: insights fresh, no context loss
• Risk: may max out mid-planning

Capacity unknown:

• Set Level 0 very low
• Let the period reveal capacity
• Retro will capture what was actually possible

Planning-Retro (Meta-Improvement)

At end of planning session, briefly reflect:

• What worked about this planning process?
• What was awkward or missing?
• Skill updates needed?

Document in Notes section of plan.

Flexibility

Structure is guide, not prescription:

• Skip sections if not relevant
• Add domain-specific sections
• Adapt length to complexity
• Focus on actionable over comprehensive

Different scales, same muscles:

• Daily planning is quick (5-10 min)
• Weekly planning is medium (20-30 min)
• Monthly+ planning is deeper (45-60 min)
• Same structure, different depth