Annual Planning

Annual Planning

When to Use This Skill

Use this skill when you need to:

• Create a comprehensive annual business plan with goals and milestones
• Break yearly objectives into quarterly and monthly targets
• Allocate resources (time, money, energy) across priorities
• Set a strategic direction for the coming year with measurable outcomes

DO NOT use this skill for weekly planning, project planning, or financial forecasting. This is for high-level annual strategic planning.

Core Principle

AN ANNUAL PLAN IS NOT A WISH LIST — IT IS A RESOURCE ALLOCATION DOCUMENT THAT FORCES YOU TO SAY NO TO GOOD IDEAS SO YOU CAN SAY YES TO THE BEST ONES.

Phase 1: Reflect

Review the past year before planning the next one.

Required Inputs

Year in Review Template

## [Previous Year] in Review

**Revenue:** $[X] ([+/-X%] vs. prior year)
**Top 3 Wins:**
1. [Win + impact]
2. [Win + impact]
3. [Win + impact]

**Top 3 Misses:**
1. [What was planned + why it didn't happen]
2. [What was planned + why it didn't happen]
3. [What was planned + why it didn't happen]

**Key Lesson:** [One sentence]

**What to keep doing:** [Activities that drove results]
**What to stop doing:** [Activities that wasted time]
**What to start doing:** [New activities for next year]

GATE: Complete the review before setting new goals.

Phase 2: Set Goals

Define the annual vision and break it into goals.

Annual Theme

Every year gets a single theme — one word or phrase that guides every decision:

**[Year] Theme:** [e.g., "Scale," "Profit First," "Foundation Building," "Diversify"]

Goal Framework

Set 3-5 annual goals using this structure:

## [Year] Goals

### Goal 1: [Specific, Measurable Outcome]
**Metric:** [How you measure success]
**Target:** [Number or milestone]
**Why it matters:** [Connection to business vision]
**Resources needed:** [Time, money, people]

### Goal 2: [Specific, Measurable Outcome]
...

Goal Quality Check

Every goal must pass these tests:

• Specific: Can you explain it in one sentence?
• Measurable: Is there a number or clear milestone?
• Achievable: Do you have the resources to pursue it?
• Relevant: Does it connect to the annual theme?
• Time-bound: Does it have a deadline within the year?

GATE: Confirm annual goals before cascading into quarters.

Phase 3: Quarterly Cascade

Break annual goals into quarterly milestones and monthly actions.

Quarterly Milestone Map

## Quarterly Milestones

### Q1: [Theme — e.g., "Build Foundation"]
| Goal | Q1 Milestone | Key Actions | Success Metric |
|------|-------------|-------------|---------------|
| Goal 1 | [Milestone] | [2-3 actions] | [Metric] |
| Goal 2 | [Milestone] | [2-3 actions] | [Metric] |

### Q2: [Theme — e.g., "Launch and Test"]
| Goal | Q2 Milestone | Key Actions | Success Metric |
|------|-------------|-------------|---------------|
| Goal 1 | [Milestone] | [2-3 actions] | [Metric] |

### Q3: [Theme — e.g., "Optimize"]
...

### Q4: [Theme — e.g., "Scale and Prepare"]
...

Resource Allocation

## Resource Allocation

| Resource | Total Available | Goal 1 | Goal 2 | Goal 3 | Buffer |
|----------|---------------|--------|--------|--------|--------|
| Time (hrs/week) | [X] | [X] | [X] | [X] | [X] |
| Budget | $[X] | $[X] | $[X] | $[X] | $[X] |
| Team capacity | [X people] | [X] | [X] | [X] | — |

Rule: Always allocate a 10-20% buffer for unexpected opportunities or emergencies.

Phase 4: Execution System

Set up the rhythm that keeps the plan alive throughout the year.

Review Cadence

## Planning Review Rhythm

**Weekly (15 min):** Review this week's actions against monthly targets
**Monthly (30 min):** Review monthly progress against quarterly milestones
**Quarterly (2 hours):** Full quarterly review — adjust goals, reallocate resources
**Annually (half day):** Full annual review and next year planning

Quarterly Review Template

## Q[X] Review

**Goal progress:**
| Goal | Target | Actual | Status | Adjustment |
|------|--------|--------|--------|-----------|
| [Goal] | [Target] | [Actual] | On track / Behind / Ahead | [Change if needed] |

**What worked this quarter:**
**What didn't work:**
**Adjustments for next quarter:**

Annual Plan One-Pager

Distill the entire plan into a single page that can be posted visibly:

## [Year] Annual Plan — One Page

**Theme:** [Word/Phrase]
**Revenue target:** $[X]
**Top 3 Goals:**
1. [Goal + target metric]
2. [Goal + target metric]
3. [Goal + target metric]

**Q1 Focus:** [One sentence]
**Q2 Focus:** [One sentence]
**Q3 Focus:** [One sentence]
**Q4 Focus:** [One sentence]

Anti-Patterns

• Too many goals — more than 5 annual goals means nothing gets the focus it needs. Ruthlessly prioritize.
• No quarterly milestones — annual goals without quarterly checkpoints drift until December panic.
• Planning without reviewing — skipping the year-in-review means repeating last year's mistakes.
• No resource allocation — goals without time and budget attached are fantasies, not plans.
• Set it and forget it — the plan is a living document. Quarterly reviews keep it relevant.

Recovery

• User has never done annual planning: Start with just 2 goals and quarterly milestones. Add complexity in future years.
• Last year had no clear goals: Use revenue, customers, and personal satisfaction as proxy metrics for the review.
• User sets goals too aggressively: Apply the "50% rule" — if you achieve 50% of an aggressive plan, is that still a great year? If yes, keep it. If not, scale back.
• Mid-year and no plan exists: Do a mid-year plan. Same process, 6-month horizon. Better late than never.
• User is overwhelmed by the process: Complete it in two sessions — Session 1 for review and goals, Session 2 for quarterly cascade and execution system.