# Annual Planning > Facilitates annual business planning with vision setting, goal cascading, quarterly milestones, and resource allocation for focused execution. - Skill: `reaperinvest/annual-planning` (Agent Skill) - Install (CLI): `npx skillmds@latest add reaperinvest/annual-planning` - Raw SKILL.md: https://api.skillmd.com/api/skills/reaperinvest/annual-planning/raw - Safety review: pending - Works with: Claude Code, Claude.ai, OpenAI Codex - Category: Coding & Dev Tools - Author: reaperinvest (https://skillmd.com/u/reaperinvest) - Updated: 2026-09-22 - Page: https://skillmd.com/skills/reaperinvest/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 | 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.