---
name: annual-planning
description: "Facilitates annual business planning with vision setting, goal cascading, quarterly milestones, and resource allocation for focused execution."
allowed-tools: Read Write Glob
metadata:
  author: matthewhitcham
  version: "1.0"
---

# 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

| Input | What to Ask | Default |
|-------|------------|---------|
| **Last year's revenue** | "What was your revenue last year?" | No default |
| **Last year's wins** | "What were your top 3 accomplishments?" | No default |
| **Last year's misses** | "What did you plan to do but didn't?" | No default |
| **Biggest lesson** | "What is the one thing you learned about your business this year?" | No default |
| **Current team** | "Who is on your team and what do they handle?" | Solopreneur |
| **Available budget** | "What is your approximate budget for growth initiatives?" | Limited |

### 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.
