With the year winding down and the holidays on the way, there is a unique opportunity for entrepreneurs. In the festive chaos, it is the right time to pause, and plan what is to come. But, whatever the case, how can you juggle your whirlwind with strategic business planning at this time of year? Let’s dive in.
Why the Holiday Season is Ideal for Strategic Planning
That’s probably the weirdest and most inappropriate time to discuss business planning. After all, isn’t this when you take a break? Not necessarily. Here’s why this period is actually a goldmine for strategy:
Reflecting on the Year’s Successes and Challenges
Before you look ahead, look back. What worked this year? What didn’t? We rush into the future without grasping how we have preformed in the past.
- Wins to Celebrate: Did you hit a major milestone? Land a key client? These moments shouldn’t just motivate, but they’ll also show you what you’re doing right.
- Lessons Learned: Maybe a campaign flopped or a new hire didn’t work out. It’s fine, failures are better lessons than successes.
Slower Pace, More Thinking Time
Let’s be real: But things usually slow down in December unless you’re in retail or hospitality. Take advantage of this quieter period and work through big picture questions that get swept aside in the operation of day-to-day life.
Setting Clear Goals for the Coming Year
After your reflection, it’s time to dream big. Or small. Whatever fits your vision.
The Power of SMART Goals
You’ve probably heard it before: If your goals lack these five elements, then you don’t have real goals. goals should be Specific, Measurable, Achievable, Relevant, and Time-bound. But let’s unpack that with examples:
If you aren’t yet ready to change your goal from “Grow my business,” try “Increase revenue by 20% by Q4 next year.”
To achieve that goal, you can easily swap the statement, ‘Improve Marketing,’ with ‘Launch three targeted email campaigns by June’ (or sometime in June).
Prioritizing Goals: The Eisenhower Matrix
If like me, you have too many ideas, use the Eisenhower Matrix to organize them. Split tasks into four categories:
- Urgent and important
- Important but not urgent
- Urgent but not important
- Neither urgent nor important
Pay attention to Quadrant 2 – important but not urgent – where real growth takes place.
Planning in Harmony with the Holidays
Let’s face it: When combined with family gatherings, travel plans, and endless cookies, it’s easy to lose momentum. What’s a holiday Scrooge to do, then, if not blowing the holidays wide open?!
Balance Work and Festivities
You’re not being a robot. Set aside time for strategic planning, and time for holiday cheer. Working too much during this time can cause burnout, which I don’t think anyone really wants starting in January.
- Time Blocking: Dedicate specific hours for business planning and stick to them.
- Celebrate Small Wins: Completed your Q1 plan? Don’t forget to reward yourself with that holiday treat or evening off.
Leveraging Holiday Spirit for Creativity
In fact, all that festive atmosphere can feed your creative juices. Swap out your doodle board with a stroll through a holiday market or pick up the phone to a friend for a goal talk. You can have some inspiration from the most unlikely sources.
Tools and Techniques for Effective Planning
No one plans in a vacuum. Here are a few tools and strategies to keep you organized and inspired:
Vision Boards: Not Just for Pinterest
By visualising your goals they can feel more tangible. Make a digital or physical vision board populated with images, words, and sketches of what you’d like to accomplish in 2024.
Business Planning Software
Platforms like Trello, Notion, or Asana can help you map out tasks and deadlines. They can be used to make a roadmap for your year.
SWOT Analysis
Don’t skip the classics. A SWOT analysis (Strengths, Weaknesses, Opportunities, Threats) is a great simple way to assess how your business stands.
Building Flexibility into Your Plan
The best laid plans don’t mean anything. One lesson entrepreneurs took away in recent years: Expect the unexpected. Here’s how to stay nimble:
Scenario Planning
Dream up a couple ‘what if’ scenarios. If your key supplier raises prices, what then? Or if demand suddenly spikes? It saves your heads later thinking of likely challenges now.
Regular Check-Ins
Next December won’t be here before you know it; so don’t wait until then to revisit your plan. Schedule quarterly reviews to see if what you’re doing is working and adjust as necessary.
Leveraging the End-of-Year Energy
Ring in the new year and a new year usually comes with a combination of excitement and nostalgia. That energy needs to be harnessed and used to fuel the planning.
Gratitude as a Business Strategy
Giving thanks isn’t just good manners; it’s good business. Thank your clients, your partners and, of course, your team. In fact, a little appreciation goes a long way in keeping relationships on track.
End-of-Year Networking
Connecting with peers and potential collaborators is a prime occasion during holiday events. Gather and exchange ideas with these gatherings.
Looking Ahead with Confidence
In other words, holiday season isn’t a relaxing time—it should be one of work, getting ready for what’s next. Reflecting on the past, allowing us to set clear goals and plan with intention, allows us to step into the new year with confidence and clarity.
You don’t have to overthink strategic planning, because it doesn’t have to be perfect. All it needs to be is actionable. So get yourself a cup of hot cocoa, find yourself some quiet time and start plotting out your biggest, brightest year yet.
Happy planning—and happy holidays!





