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Annual Planning Dēmĭstəfīed

Annual Planning Dēmĭstəfīed

Create a plan for your business to bring your idea to life --> swipe files included 📑

Nile Harris
January 06, 2025

In partnership with

Demystifying the gap between ideas and execution.

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MIND THE GAP

One of the biggest mistakes a solopreneur, independent, or start-up can make is not planning.

Make no mistake, poor planning can lead to wasted time, money, and energy. It makes it easy to get distracted and can widen the gap between an idea and execution.

This is the primary reason for the strategy-to-execution gap.

CLOSE THE GAP

Having a plan will help you prioritize your resources and work. It will also make it easy to know what to say yes to and keep you on track.

Best practice is to start this process before the end of the prior year. But so what if you didn’t? Starting at the beginning of the year works too.

For solopreneurs and side hustlers

Annual planning doesn’t have to be overwhelming. Keep it simple. Focus on what will yield the most results, such as growing your email list, improving your product, or carving out more time to develop your craft further.

For startups and midsize companies

Take a collaborative approach. Engage your team early and often in the planning process. Your job is to ensure alignment and keep the focus on what truly matters.

By the end of this edition, friend, you will not only understand the importance of annual planning but also how to get started, measure your progress, and find helpful resources, including some of my favorite swipe files and templates.

⏱️ Reading time: 8 minutes

Why annual planning matters
Clarify your vision
Prioritize effectively
Allocate resources wisely
Plan and execute
Measure your success
Annual planning checklist, swipe files, and resources
Generate ideas
Mindset shift
Online communities
TL;DR
Before you go

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Why annual planning matters.

Annual planning bridges the gap between where you are and where you want to be. It gives you a structured framework to:

Clarify your vision
Prioritize effectively
Allocate resources wisely
Measure your success

It’s more than setting lofty goals. This is where and when you create actionable and adaptable roadmaps for yourself, your team, and your business.

Although it’s best to do it before you start or the year prior, the most important thing is that you do it.

Even if it’s just you right now, organizing your thoughts will save you time, energy, and resources. It also helps to prevent distraction from your goal.

Clarify your vision.

Start with reflection.

What worked well this year? Celebrate your wins.
What didn’t go as planned? Extract the lessons, not excuses.
Check the alignment between your goals and your actions. Did you do what you said you would do?

Define your big-picture goals.

Set no more than 3-5 overarching goals for the year.
Use the SMART framework (Specific, Measurable, Achievable, Relevant, Time-bound).
For solopreneurs or small teams, focus on goals that align with your capacity.

Prioritize effectively.

Break it down.

Translate annual goals into quarterly priorities.
For each quarter, define key results or milestones.
Use tools like OKRs (Objectives and Key Results) to measure results and make corrections as you go.

Plan your execution.

Map out actionable steps for each quarter.
Assign ownership and set deadlines.
Leverage tech tools to automate and stay organized.
Create accountability systems.

Allocate resources wisely

Build in flexibility.

Life happens. Your plan should allow for recalibration.
Schedule mid-year reviews to adjust as needed.

Watch the budget.

Decide what is a need-to-have versus a nice-to-have.
Keep track of every expenditure. Small expenses add up quickly.
Use a spreadsheet or tools like Wave or Quickbooks to keep up with your money all year.
Don’t wait until the end of the year to record your expenses. Do it monthly.

Watch your time.

It’s easy to spend time on operational tasks because they’re controllable. Focus most of your time on revenue-generating activities. Outsource what you can.
Perfection is the enemy of progress. Put something out there, get feedback, then iterate.

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Plan to execute. Execute the plan.

Follow these simple steps to create an action plan. One of solopreneurs’ and independents' biggest mistakes is not carefully considering what they want to accomplish and how. It’s okay if the plan changes, but starting with a plan is essential.

Set aside time. Dedicate uninterrupted time for annual planning—at least one full day.
Gather data. Review performance metrics, financial reports, and customer feedback.
Identify key themes. What trends or patterns emerge?
Brainstorm. Get all your ideas out before refining them into actionable goals.
Prioritize. What’s most essential and feasible, given your resources?
Document the plan. Use a tool like Notion, Asana, or a simple spreadsheet. My favorite framework is the Business Model Canvas.
Communicate. If you’re a team, share the plan and rally everyone around it. If it’s only you, revisit your plan monthly, especially when you’re distracted.

What matters gets measured…

and what gets measured gets done.

Measure your progress.

Set up automation to track your progress.
Use dashboards, KPIs, or simple check-ins weekly.
Correct and continue if you find something isn’t working well.
If social media is a significant part of your strategy, use tracking platforms to determine what’s working.

Celebrate your wins.

Celebrate wins (big and small) to sustain momentum.
Reward yourself, your teams, or your referral partners.
You will have lows. Celebrate the lessons learned.

💡 Annual Planning Checklist + Swipe Files 💡

📑 = download swipe file

Reflection Prompts
- What’s my one word for this year?
- What’s one thing I’ll stop, start, and continue doing?
- What is one thing I WANT to accomplish by the end of the year?
- What is one thing I MUST accomplish by the end of the year?
- What is my biggest challenge to achieving my goals this year?
- Do I have the right mindset?
- What is one thing I must master this year to be successful?
- Who can I connect with to make the journey more fun?
Planning and Tracking Frameworks
- OKRs (objectives and key reports)
- KPI (key performance indicators)
- Balanced Scorecard
- SWOT (strengths, weaknesses, opportunities, results) analysis
- 📑 Business Model Canvas (read more about the Business Model Canvas)
- 📑 Customer journey mapping
Productivity and Planning Software
Mind Mapping and Creative Thinking
Financial Tracking and Reporting

🚉 Visit the Gap Dēmĭstəfīed archive for more resources!

🤝 Go Together 🤝

These are some online communities that can help find like-minded people on a similar journey.

The Consulting Collaborate for K12 education (invite only; ask me about it)
Reddit Consulting (subreddit on Reddit)
The Escapee Collective
Fractional United
Ladies Get Paid
Freelancing Females
Freelancers Union
CMO Alliance
Consultancy
Pollen

THE GAP DĒMĬSTəFĪED

Take time to plan your path to avoid falling into the strategy-to-execution gap. This will significantly increase your probability of success.

Whether you are a solopreneur, small team, startup, or mid-size company, focusing on your plan and measuring your outcomes will improve your chances of success by keeping what’s mission-critical in front of you and what’s unimportant out of view.

Clarity: A clear understanding of your objectives.
Focus: Direction on where to spend your time and energy.
Alignment: For teams, everyone pulls in the same direction.
Motivation: Seeing a realistic, step-by-step path inspires action.
Measurability: Clear metrics to track and celebrate success.

TL;DR: Plan meticulously and adapt rapidly. A plan will keep you on track by providing clarity, marshaling your resources, and focusing your efforts.

Why annual planning matters. A plan will help you clarify your vision, prioritize effectively, allocate resources wisely, and measure your success.
Clarify your vision. Layout a vision for where you want your idea or business to be and how you will get there. Describe what the world will look like for you.
Prioritize effectively. You can’t do everything, and everything isn’t worth doing. Focus the majority of your effort on revenue-generating activities instead of operational tasks.
Allocate resources wisely. Small expenses tend to sneak up on you. Create a system and use a tool to track expenses monthly. Prioritize the investment in resources that will provide the greatest return.
Plan and execute. Use a tool to write your plan down and follow it. Written plans have a greater probability of success. Use a framework like the Business Model Canvas to organize your thoughts.
Measure your success. What matters gets measured, and what gets measured gets done. Determine your KPIs and use a framework to track important metrics consistently, and modify the plan accordingly.
Annual planning checklist, swipe files, and resources. Get your hands on some of my favorite resources and templates to help you plan, create goals, and track your progress.
Online communities. You’re not alone. Millions of people are in the same place you are. These are a few online communities that you can join to share best practices, swap stories, and cheer each other on. Many collaborations have been born from these communities.