Hey there,
In about three weeks, you won't have time to think. The holiday rush will take over, then it's New Year's, and suddenly it's February and you're running the business the same way you did last year.
That's why the smartest owners do their planning now, in early November, while there's still a little breathing room. And with AI, what used to take a weekend retreat and a pile of spreadsheets now takes a single focused afternoon.
Here's how to look back at this year, spot what's working, and walk into 2027 with a plan.
START WITH AN HONEST LOOK BACK
Before planning forward, find out what actually happened. Pull a few basics: monthly sales, your top products or services, your biggest expenses, and where new customers came from. Then paste it into AI:
"Here's a summary of my business this year: [paste sales by month, top sellers, main expenses, customer sources]. Help me understand it: What were my strongest and weakest months, and why might that be? What's making me the most money? What's costing more than it's worth? Explain it in plain English."
You'll often spot something you missed, like a product quietly carrying the business or a monthly subscription nobody uses.
PICK THREE GOALS, NOT TWELVE
Most plans fail because they try to do everything. Ask AI to keep you focused:
"Based on this review, suggest three realistic goals for my business next year that would make the biggest difference. For each, explain why it matters and the first small step to get started. I'm a small business with limited time and budget."
Three goals you actually chase beat a dozen you forget by March.
TURN GOALS INTO A 90-DAY PLAN
A year is too big to act on. Break your first quarter down:
"Turn these three goals into a simple 90-day plan for January to March. List what I should do each month, and keep each month to 3-4 specific actions. Make it realistic for a busy owner."
Print it, stick it by your desk, and review it every Monday.
GET AHEAD OF TAX TIME WHILE YOU'RE AT IT
Year-end is the moment to make smart money moves before the calendar flips. Ask AI to draft a list of questions for your accountant: "What year-end questions should a small business owner ask their accountant in November to prepare for taxes and plan for next year?" Then book that call now, before their calendar fills up.
THE GUARDRAILS
AI is your thinking partner, not your accountant. Use it to organize and understand your numbers, but confirm tax and financial decisions with a qualified professional.
Protect sensitive data. Summarize your numbers instead of uploading full bank statements or customer lists with personal details.
Be honest with the inputs. If you only feed AI your good months, you'll get a rosy plan that doesn't help. Include the rough patches.
YOUR ACTION PLAN THIS WEEK
Block one afternoon. Run the look-back prompt, pick your three goals, and build your 90-day plan. Then book your year-end accountant call. You'll head into the holiday rush knowing exactly what January looks like.
Know an owner who says "I'll plan next year after the holidays" every single year? Forward this. This is the week to do it.
Talk soon,
Dave
The AI Playbook
