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

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. Create Empty Framework First

⚠️ CRITICAL: Create structure-only artifact BEFORE filling content.

Process:

1. •Generate empty artifact with all section headers
2. •Present to user: "Here's the structure we'll fill in together"
3. •Briefly explain each section's purpose
4. •Then proceed to fill ONE SECTION AT A TIME

Why this matters:

• •User sees the whole picture before diving in
• •Reduces cognitive load (knows what's coming)
• •Enables reactions over generation
• •Catches nuances that full-draft approach misses

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]

---

## Constraints

**Fixed:**
- [Non-negotiable deadlines, appointments]
- [Known drains or high-effort days]

**Important Dates (Weekly+):**

| Date | Event | Notes |
|------|-------|-------|
| [Date] | [Event] | [Context] |

---

## 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

**Aligned to success levels:**

**Level 0-1 (Foundation/Base):**
- [Experiment supporting minimum viable progress]

**Level 2 (Target):**
- [Experiment for good week given capacity]

**Level 3 (Reach):**
- [Stretch experiment if everything aligns]

---

## Week Structure (Weekly Plans)

**Include for weekly plans. Day-by-day focus mapping.**

| Day | Date | Focus | Key Activities |
|-----|------|-------|----------------|
| Mon | [Date] | [Primary focus] | [1-2 activities] |
| Tue | [Date] | [Primary focus] | [1-2 activities] |
| ... | ... | ... | ... |

---

## 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 ONE SECTION AT A TIME

⚠️ CRITICAL: Do not generate full document on first pass.

Pattern per section:

1. •Make suggestion based on constraints + retro data
2. •Ask ONE focused question about that suggestion
3. •Wait for user response
4. •Update artifact in real-time
5. •Confirm before moving to next section

Interpreting user responses:

• •"proceed" / "continue" / "this is fine" = move to NEXT SECTION, not skip to end
• •"good enough" = section approved, move on
• •"let's discuss" = stay in this section, go deeper

Do NOT:

• •Generate full document then ask for rubber stamp
• •Interpret "proceed" as permission to finish everything
• •Skip the conversational calibration on Success Levels

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.

Important: These levels become the primary assessment criteria in the retrospective. Write them clearly so future-you can assess each criterion with ✓/✗.

Decision Filter (Monthly+)

For monthly and longer plans, create a 2-question filter to test proposed activities.

Every activity should pass both questions to proceed. This prevents scope creep and keeps focus on what matters.

Template:

1. •Does this [action aligned with theme]?
2. •Does this [build toward next milestone]?

Examples:

Month 1 (Build Foundation):

1. •Does this build toward the target distance/skill?
2. •Can I sustain this without injury/burnout?

Month 2 (Increase Volume):

1. •Does this increase capacity appropriately?
2. •Does this maintain recovery balance?

Month 3 (Race Prep):

1. •Does this prepare me for the target event?
2. •Does this avoid overtraining before the goal?

Usage: When new opportunities or tasks arise mid-period, run them through the filter. Both YES = proceed. One NO = defer or delegate. Both NO = decline.

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