Why the Best Creative Leaders Plan in December (Not January)
I learned this lesson the hard way.
Years ago, when I was working in ministry, we had this pattern every single year. December would hit, and we'd all just survive the chaos—Christmas services, year-end events, the whole nine yards. Then January 1st would roll around and we'd think, "Okay, NOW we can plan our year."
So we'd spend the entire month of January locked in planning meetings. Strategy sessions. Goal setting. Vision casting. All that good stuff.
And you know what happened? By the time February hit, we were scrambling to build back the margin we'd lost in January. We'd spent four weeks planning while the work kept piling up. Then we spent the next few months playing catch-up on everything we should have been executing in Q1.
That's when I realized: January planning isn't proactive. It's reactive.
The Problem with January Planning
Here's what most creative agencies do every December:
Survive the holiday chaos
Sprint to finish end-of-year client deliverables
Promise themselves they'll "figure everything out in January"
Collapse into the holidays completely exhausted
Then January 1st arrives. Fresh start, right? New year, new possibilities!
Except... the new year has already started. You're already late.
While you're spending the first two or three weeks of January planning your year, your competitors who planned in December? They're already executing. They hit the ground running on January 2nd because they did the thinking in December.
You can't plan and execute simultaneously without losing margin. That's not a bug—it's a feature of how time works.
Look, I get it. December is already overloaded. Calendar chaos. End-of-year client sprints. Holiday commitments. Budget conversations. Performance reviews. The list goes on.
But here's what I've learned: If you strategically make December a planning month, you create margin in Q1 instead of destroying it.
Think about it this way: You have 31 days in December. Use the first 20 days for working AND planning. Then use the last 11 days for rest. You can have both—working time and rest time—just not simultaneously. That's why you plan this just like everything else that gets successfully executed.
Because when January hits, you're not trying to figure out what to do. You already know. You planned it in December when your brain had space to think strategically instead of reactively.
If you've been following me for any length of time, you know I'm obsessed with the DO vs DUE framework. The whole premise is this: Plan the work, then work the plan.
December planning IS planning the work. It's setting your DO dates before the DUE dates start screaming at you.
Think about what happens in a typical January without December planning:
New client budgets and commitments get made in late December/early January
You carry old-year clutter, habits, and stress into the new year
You're making decisions about Q1 work while you're still recovering from Q4 exhaustion
Every decision feels urgent because you have no buffer
That's the opposite of margin. That's deadline-driven chaos with a "New Year, New Me" Instagram filter on it.
But when you plan in December, you're creating the buffer BEFORE you need it. You're looking at your 12-month outlook and asking: What needs to happen in Q1 for Q4 to be successful? What projects need DO dates in February so their DUE dates in March don't kill us?
December planning creates margin in Q1 because you're thinking proactively about the whole year, not reactively about the next two weeks.
The 12-Month Outlook Advantage
Here's what I do every December with my clients: We build out their 12-month outlook.
Not just Q1. Not just "first quarter goals." The WHOLE year.
Why? Because when you can see the entire year laid out, you start making different decisions:
You schedule that team retreat in March instead of May because you can see the client load coming in Q2
You plan your speaking engagements around your project delivery schedule instead of saying yes to everything
You identify the months that need to be "revenue months" versus "investment months"
You build in actual rest—fuel and renewal days, not just "I'll rest when the project is done" promises
This is proactive leadership. This is planning the work so you can work the plan.
And it only works if you do it in December.
You don't need the entire month locked in a conference room. You need strategic pockets of time:
Week 1-2 of December: Review 2025. What worked? What didn't? What are we keeping? What are we killing? (If you caught last week's episode about subtraction before addition, you know why this matters.)
Week 3 of December: Build your 12-month outlook. Map out major projects, client commitments, team capacity, revenue goals, and margin months.
Week 4 of December (before Christmas): Communicate the plan to your team. Get their input. Make adjustments. Lock it in.
Last week of December: REST. Actually rest. Because you already did the thinking.
Then January 2nd? You execute. No scrambling. No "we'll figure it out as we go." You already figured it out.
I know what you're thinking: "But Dustin, I need rest in December too. Isn't this just hustle culture with better branding?"
No. Here's the difference:
Hustle culture says: Work through December, work through January, work through everything, rest is for the weak.
Strategic planning says: Work AND plan in the first 20 days of December, then actually rest for the last 11 days because you're not carrying "I need to figure out January" stress into the holidays.
The irony is that people who skip December planning often don't actually rest over the holidays. They're mentally spinning about January the whole time. They're thinking about goals at Christmas dinner. They're sketching out ideas on New Year's Day.
But when you plan in December? When you get to December 20th and your 12-month outlook is done? You can ACTUALLY rest. Because the thinking is done. The plan exists. You're not carrying that cognitive load anymore.
That's not hustle culture. That's strategic rest.
What's At Stake If You Don't Plan in December
Let me be brutally honest about what happens when you wait until January:
You miss opportunities. That perfect client who reaches out January 3rd? You can't give them a clear timeline because you don't know your own capacity yet.
You make reactive decisions about money. Q1 budget conversations happen in late December/early January. If you haven't planned your year, you're guessing at what you need instead of knowing.
Your team loses confidence in your leadership. When you're three weeks into January and still "figuring out our priorities," your team starts to wonder if you know what you're doing.
You burn margin before you need it. Every day you spend planning in January is a day you're not executing. That's lost revenue, lost momentum, and lost margin that you'll be desperately trying to recover in February and March.
You repeat last year's mistakes. Without December reflection and planning, you bring all of last year's problems into this year. Same client issues. Same capacity problems. Same stress patterns. Different calendar year.
Want help building your 12-month outlook before the new year? Let's talk. I help creative agencies build systems that create margin instead of consuming it—and it starts with planning in December, not January.