The Art of Ending Well: How December Can Set Up a Stronger 2026
- Terrand Smith
- 7 hours ago
- 4 min read
December can feel like a whirlwind for small business owners. Between the rush of holiday sales, fulfilling customer orders, and juggling end-of-year obligations, the thought of annual planning might feel impossible. But here’s the truth...
You don’t need to do heavy planning in December. Instead, this month is the perfect time to create the space and clarity you’ll need to plan well in January or February.
At 37 Oaks, we often guide our business owners through annual planning strategies within the first two months of the year. It’s a rhythm that works because it allows December to be about reflection, closure, and preparation, not overloading an already intense season. One of the tools we lean on during this time is the Prepare to Shift. I wrote this workbook in 2022, and it is designed to help small businesses process where they are, where they want to go, and the shifts required to get there. December is a natural moment to pause and take inventory of those shifts.
Step 1: Pause and take a quick health check
Before the calendar flips to a new year, take a few moments to glance back at the one you’re closing out. Look at your sales, expenses, and cash flow at a high level. What worked well? What areas caused the most stress? Don’t get bogged down in the details; this is about taking the temperature of your business. Jot down a few notes so you have a starting point when you sit down to plan in January.
Step 2: Organize the data you’ll need later
One of the biggest time drains in annual planning is scrambling to find data. Make December the month you set yourself up for success by gathering it now. Create a simple list or folder of where your performance data resides - your POS system, social media analytics, accounting software, website traffic, customer lists, or any other tracking system you use. That way, when it’s time to analyze your year, you won’t waste precious hours searching.
Step 3: Clear the clutter and close loops
A fresh year feels a lot lighter when you’re not carrying over unfinished tasks. Use December to wrap up loose ends: follow up on unpaid invoices, finalize outstanding customer orders, and close any lingering projects.
At the same time, take a few minutes to clear your physical and digital workspaces. Delete outdated files, back up important ones, and tidy up the piles on your desk. You’ll be surprised at how much clearer your mind feels when your environment matches the fresh start you want to create.
Step 4: Reflect before you plan
In the middle of all the busyness, carve out just 30–60 minutes for reflection. Ask yourself: What am I most proud of this year? What would I do differently? What opportunities do I see ahead?
This is where the Prepare to Shift workbook can also be an invaluable tool. Its exercises help you identify where you’re holding on to old habits that may be slowing you down, and where you’re ready to embrace new strategies for growth. December is the ideal time to work through a few pages, even if it’s just one or two chapters.
Step 5: Protect your planning time now
One of the easiest ways to ensure you actually plan in the new year is to block the time before your calendar fills up. Schedule one to 2-4 full days between January and February for annual planning and treat it like a non-negotiable appointment. By protecting the time now, you’ll avoid the common trap of “I’ll get to it later", and later never comes.
Step 6: Recharge your energy and mindset
Your business can only be as strong as the person leading it. December is the perfect time to take a breather. Prioritize sleep, spend time with loved ones, and give yourself permission to unplug, even if just for a few hours at a time.
If you need help shifting gears, pick up resources that encourage reflection and renewal. The Prepare to Shift workbook is designed for exactly this moment—it helps you slow down, re-center, and see your business with fresh eyes. Other inspiring books, podcasts, or articles can also give you new energy and perspective heading into the new year.
Step 7: Show gratitude and celebrate your wins
Finally, pause to thank the people who supported your business this year: your customers, your team, your support system, and even yourself. Send a note of appreciation, write a social media post, or simply take a quiet moment to acknowledge the effort it took to get here. Celebration, no matter how small, fuels the motivation you’ll need for the year ahead.
Final Thoughts
You don’t have to cram annual planning into the most stressful month of the year. December can be your reset button. By reflecting, closing loops, organizing data, and recharging your energy now, you’ll walk into January with a clear head and everything you need to create a strong, thoughtful plan.
And if you need a little help, the Prepare to Shift workbook is a great companion. Its simple, guided exercises will help you uncover what’s holding you back, identify where you need to pivot, and step confidently into the year ahead.
When you give yourself the space to prepare, you set the stage for a year of intentional growth. Download this simple December Reset Checklist to get started.
Prepare to Shift: The Workbook
Prepare To Shift is a workbook that outlines proven principles to shift your business from the early startup/hobby stages to growth. With close to 20 years of corporate retail experience, 10 years as a successful entrepreneur, and 15 years coaching small business owners nationwide, Terrand Smith walks you through the mindset and action shifts every entrepreneur needs to take their business to the next level.
Each principle in this workbook includes an exercise that uncovers strengths, opportunities, and next steps for both you and your business. By the end of this workbook, you will have the tools necessary to unstick and a road map to guide you toward growth.
This quick and easy read makes the complexities of growing a business more digestible and manageable. It is a must-read for any early-stage entrepreneur, a loved one who recently started a business, or a supplement to any entrepreneurial or business program.
Who is 37 Oaks?
37 Oaks is an education company that strengthens communities by transforming small businesses into valuable, commerce-driven assets. Our goal is to empower them through Commerce, Innovation, and Strategy.
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