Every January, I take one day completely off from client work, turn off my phone, sit in a quiet room (usually a rented co-working space I don’t normally use — the change of environment matters), and plan my year. Just me, a notebook, a laptop with my business data, and six hours of focused thinking.
This annual planning day has been more valuable than any conference, workshop, or mastermind I’ve ever attended. Not because the exercises are complex — they’re not. But because as a solo founder or small business owner, you almost never give yourself permission to stop working IN the business and spend a full day working ON it.
The rest of the year is reactive. Clients need things. Emails arrive. Content needs publishing. Bills need paying. The annual planning day is the one time I’m fully proactive — looking at where the business is, where I want it to go, and what specifically needs to change to get there.
Here’s the exact agenda I use, including the six exercises and the outputs each one produces.
Pre-Retreat Preparation (The Evening Before)
The retreat day should be 100% thinking and deciding, not data gathering. Prepare the evening before:
Pull your financial data: Full-year revenue, expenses, profit, and profit margin. Revenue broken down by source (clients, products, services). Client profitability if you track it.
Review your quarterly reviews: Open your quarterly review documents from the past year. Note which objectives you hit and which you missed.
Collect your notes: Any “someday” ideas, frustrations, opportunities, or observations you’ve captured throughout the year. I keep a running note on my phone called “Annual Review Ideas” that I add to whenever something strikes me.
Print your one-page business plan from last January. You’ll compare it to reality.
Total prep time: 1-2 hours the evening before.
Exercise 1: The Year in Review (60 minutes)
Start by looking backward. Pull out your data and your quarterly reviews.
Question 1: What worked? List every significant win from the past year. Revenue milestones, client successes, systems built, content published, relationships developed. Be specific: “Converted 3 clients to retainers, increasing MRR by €4,500” is better than “grew recurring revenue.”
Question 2: What didn’t work? List every significant failure, disappointment, or unfulfilled objective. A service that didn’t sell, a marketing channel that underperformed, a hire that didn’t work out, a goal you missed.
Question 3: What surprised me? The unexpected wins (a client from an unexpected industry, a content piece that went viral, a referral from someone you barely know) and the unexpected losses (a client leaving unexpectedly, a market shift you didn’t anticipate).
The insight: Look for patterns across all three lists. Your wins usually cluster around a theme — that’s your strength. Your failures usually cluster around a different theme — that’s your weakness or a misalignment. Your surprises reveal opportunities and threats you’re not systematically monitoring.
This exercise produces a one-page “Year in Review” document that becomes the foundation for forward planning.
Exercise 2: The Personal Check-In (45 minutes)
Business planning without personal planning is incomplete. Your business exists to serve your life, not the other way around.
Question 1: Am I enjoying this? Rate your satisfaction with different aspects of the business: the work itself, the clients, the income, the freedom, the challenge. Where are you most satisfied? Least satisfied?
Question 2: What do I want more of? More creative work? More client interaction? More strategic thinking? More free time? More income? Be honest, not aspirational.
Question 3: What do I want less of? Less administrative work? Fewer clients of a certain type? Less travel? Less stress? What parts of the business drain you?
Question 4: What does my ideal week look like? Describe a week that would make you genuinely happy. How many hours of client work? How many hours of creative work? How much unscheduled time? When does the work day start and end?
This exercise produces a “Personal Vision” document that acts as a filter for every business decision. If a strategic choice moves you toward your ideal week, pursue it. If it moves you away, question it.
The lifestyle vs. growth decision should be revisited during this exercise. Your answer may have changed since last year.
Exercise 3: The Financial Plan (60 minutes)
Based on last year’s data and your personal vision, build the financial plan for the coming year.
Step 1: Set your income target. What do you want to earn personally this year? Start with the personal number, then work backward to the revenue needed to support it. If you want to earn €120,000 and your business margins are 40%, you need €300,000 in revenue.
Step 2: Revenue by source. Break the target down: How much from recurring revenue? How much from projects? How much from products? This breakdown determines where your sales and marketing effort should focus.
Step 3: Expense budget. What will it cost to run the business? Fixed costs, variable costs, and planned investments. Be realistic: most founders underestimate expenses.
Step 4: Cash flow seasonality. Based on last year’s patterns, when are the high and low months? Plan your cash reserves and spending accordingly.
Step 5: Profit allocation. Using the Profit First system, set your allocation percentages for the year.
This exercise produces a one-page financial plan: revenue target by source, expense budget, and monthly cash flow projection.
Exercise 4: The Three Big Objectives (45 minutes)
Based on everything so far, define three objectives for the year. Not ten. Not five. Three.
Each objective should be:
- Measurable (a specific number or yes/no milestone)
- Personally motivating (aligned with your personal vision from Exercise 2)
- Business-advancing (moves toward your financial plan from Exercise 3)
- Achievable but stretching (you believe it’s possible but it will require focus)
Examples from my recent plans:
- “Grow monthly recurring revenue from €6,500 to €12,000 by December”
- “Publish ‘Subtract to Ship’ book 2 by September”
- “Reduce owner dependency score from 72 to 35 by December”
Three objectives give you enough to drive meaningful progress without splitting your focus so thin that nothing gets done well.
Break each objective into quarterly milestones. This creates the targets for your quarterly reviews and ensures steady progress throughout the year rather than a December sprint.
Exercise 5: The Subtraction List (30 minutes)
This is the exercise most people skip and most need. Before adding anything new to your year, subtract what’s not working.
What clients should you fire? Low-margin, high-maintenance, or misaligned clients who consume disproportionate time for disproportionately small returns.
What services should you stop offering? Offerings that aren’t profitable, that you don’t enjoy, or that dilute your positioning.
What activities should you eliminate? Marketing channels that don’t produce results, meetings that don’t produce decisions, processes that don’t add value.
What commitments should you exit? Board seats, partnerships, or ongoing obligations that no longer serve your goals.
The subtraction audit is the most powerful tool in my business arsenal because it creates space for what matters by removing what doesn’t. Do this exercise before setting your action plan — subtraction first, addition second.
Exercise 6: The Q1 Action Plan (30 minutes)
End the retreat by translating your three objectives into a specific Q1 action plan.
For each objective, define:
- The Q1 milestone (what progress looks like by March)
- Three specific actions to take in January
- The metrics you’ll track weekly
- The first thing you’ll do tomorrow
This final exercise ensures the retreat produces immediate action, not just good intentions. The Q1 plan feeds directly into your weekly CEO review, creating a direct connection between your annual vision and your daily priorities.
Total retreat time: approximately 5.5 hours plus breaks. One day. The most valuable day of your business year.
Takeaways
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Block one full day in January for annual planning. No clients, no phone, no interruptions. Change your environment. Six hours of focused thinking changes the trajectory of your entire year.
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Follow the six exercises in order. Year in Review, Personal Check-In, Financial Plan, Three Big Objectives, Subtraction List, and Q1 Action Plan. Each builds on the previous one.
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Start with personal vision before business strategy. Your business should serve the life you want. If your plan doesn’t align with your ideal week, the plan is wrong.
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Set exactly three objectives for the year. Measurable, motivating, and broken into quarterly milestones that feed into your regular review system.
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Subtract before you add. Remove clients, services, activities, and commitments that aren’t serving your goals before adding new ones. The space created by subtraction is where growth happens.
