I always try to take the last few months of the year to plan for the next one. If you’re not heads down supporting your retail stores (hopefully packed with holiday shoppers), you’re trying to squeeze in a bit of forward-looking planning. And if you’re like most people, you’re looking at last year’s numbers, this year’s incidents, and building next year’s plan around solving problems you already know about.
But here’s the thing. The problems that are going to matter most in 2026 probably aren’t the ones you’re planning for right now.
If you read this column at all… you know I’m a big fan of Malcolm Gladwell and am currently reading his newest book, Revenge of the Tipping Point. Gladwell has always paid attention to the things the rest of us scroll past. The weak signals. The small shifts. The outliers that do not make sense at first glance. He studies what everyone else ignores, not because it is loud, but because it might be important long before it becomes obvious.
Retail has lived this before. Amazon did not make a big dent in retail overnight. It arrived quietly, in ways that felt more curious than threatening. The signs were there for years. Easy to overlook. Easy to explain away. Until one day they weren’t.
Here’s my challenge to you: As you begin shaping 2026, try to make space for the parts you can’t name yet. Not just the issues sitting in reports or on spreadsheets. The ones that do not have a label or a budget line. The unease you feel when something small does not fit the pattern. That is often where the real shift begins.
Start by asking yourself these questions:
- What is the one thing that went wrong this year that you wrote off as a fluke?
- What if it was not a fluke? What if it was the beginning of something bigger?
- What are your competitors doing that makes you uncomfortable? Not because it is working, but because you do not understand why they are doing it at all?
- What technology are you dismissing as hype right now that could completely change your world in 18 months?
- What would you do differently if your budget got cut in half tomorrow? Because that kind of constraint forces innovation you would not consider otherwise.
The best plans are never built on certainty. They are built on curiosity about what might be coming. They make space for the unlikely scenarios you hope never unfold but would rather not be surprised by. They leave a little give in the system, a little room to adjust when the year refuses to line up with your S.W.A.G. business plans.
A quiet planning session is your chance to think differently. To look at the outliers instead of the averages. To connect dots that nobody else is connecting yet.
Because the trends that matter most might not be the ones you plan for every year, but the ones you might have seen if you pushed yourself just a bit more.
Happy planning.