Stop Staring at the Sunset: Why October is the Best Time for Strategic Planning
Picture this…
It’s late December, your fourth quarter is winding down, and you finally have a minute to “think big.” You grab a notebook, maybe a glass of wine, and start jotting down goals for next year. Except—you’re exhausted, your brain’s a little fried from holiday sales or events, and you’re mostly reacting to what just happened instead of shaping what’s next.
Sound familiar?
That’s why October is such a sweet spot for strategic planning. Your data from the year is mostly in, your head isn’t buried in holiday chaos (yet), and there’s still space to do something meaningful with what you’ve learned. Waiting until January is like trying to navigate by the setting sun—beautiful, sure, but not exactly forward-looking.
The Problem
When we wait until the very end of the year to plan, we lose sight of the horizon. We end up looking backward instead of ahead.
It’s tempting to hold off until you know exactly how Q4 performs—but by then, your energy (and maybe your patience) are running on fumes. Whether you’re running a shop or a product brand, the real goal is to steer your business, not just drift with the current.
Yes, pay attention to market trends—they’re valuable signals. But they’re not the captain. Your long-term vision still needs to lead the way, or you’ll spend next year reacting instead of building intentionally.
How to Approach Strategic Planning
Step 1: Change your scenery.
Big thinking rarely happens between inbox pings. Step out of your usual space—a coffee shop, a quiet park, even your car if that’s where you can think clearly. Bring your numbers (yes, all of them—the good, the bad, and the ugly) and blank sheets of paper.
Step 2: Reflect before you project.
Compare this year’s performance to previous years. Look at revenue, margins, number of accounts, or whatever KPIs matter most to you. If you like structure, try a quick SWOT analysis (strengths, weaknesses, opportunities, threats) to see your business from a higher level.
Ask yourself:
Did I reach the accounts or customers I wanted?
Which processes actually made life easier—or harder?
Who did I connect with that could open new doors next year?
What are the wins worth celebrating?
Step 3: Brainstorm without judgment.
Give yourself permission to write it all down—every half-baked idea, bold move, and small improvement. Sometimes the “what if” thoughts spark the most creative solutions.
Maybe this is the year to explore AI tools to take something off your plate. Maybe your team structure needs a shake-up. Or maybe it’s time to gather a few trusted peers who can act as your informal board of advisors—people who see your potential from a different perspective.
When you’re done, throw those ideas into ChatGPT or your favorite brainstorming tool and see what comes back. It’s amazing what a little outside perspective (human or digital) can spark.
Step 4: Pause and reset.
Once you’ve gotten it all out, take a break. Go for a walk. Have lunch. Give yourself credit for showing up early to this process—you’re already ahead of the curve. And if you’ve got trade shows, product launches, or new programs coming up early next year, this time you’ll walk into them with a plan, not a panic.
What to Do Next
Hold your planning session. Get your notes, ideas, and goals in one place.
Let it breathe. Give it a week to simmer. You’ll see what truly matters rise to the surface.
Refine and post. Turn your notes into a simple one-page visual you can pin up where you’ll see it every day—your North Star for the year ahead.
The Bottom Line
Fourth-quarter highs or lows shouldn’t define your strategy. Even a breakout product (looking at you, fidget spinners) can distract from the bigger picture.
The key is to plan with purpose, leave room to pivot, and clear your path now so you can actually take a breath and enjoy the holidays (those kids grow up so fast!). When January arrives, you’ll already know where you’re headed—and have the energy to get there.
Need help finding your rhythm for next year?
Book a Focus Finder™ Assessment and let’s chart your course before the tide turns.
