Hey there,

It’s the end of August, the patios are still full, and holiday shopping feels a lifetime away. That’s exactly why now is the moment. The businesses that win Q4 every year aren’t the ones with the biggest budgets — they’re the ones who plan in the summer and are ready to run by mid-September. Everyone else scrambles in November and leaves money on the table.

Retail sales are forecast to grow again this year, and a bigger slice of it is being decided by shoppers asking AI what to buy. You don’t need a marketing team to grab your share. You need a plan and about an hour with AI this week. Here’s the playbook.

BUILD YOUR HOLIDAY CALENDAR IN 20 MINUTES

You can’t run promotions you haven’t planned. Start with a simple calendar — a spreadsheet is perfect. Let AI build the skeleton:

“I run a [type of business]. Build me a week-by-week holiday marketing calendar from October through December. Include the key shopping moments (Halloween, Black Friday, Cyber Monday, Small Business Saturday, Christmas, New Year’s), and for each week suggest one simple promotion or post idea that fits my kind of business. Keep it realistic for a busy owner.”

Now you have a map. Everything else is just filling it in.

PLAN YOUR OFFERS BEFORE THE RUSH

The best holiday offers are decided calmly in September, not in a panic in December. Ask AI to help you design a few: “Suggest 5 holiday promotion ideas for my [business type] — a bundle, a limited-time offer, a gift option, a loyalty reward, and a last-minute deal. For each, give me a short description and who it’s aimed at.”

Pick two or three you can actually deliver, and lock them into your calendar. Done thinking about it. That’s the whole point.

WRITE THE HARD STUFF NOW, WHILE YOU HAVE TIME

The reason holiday marketing falls apart is that you’re slammed when it counts. So write it now. In one sitting, have AI draft your promo emails, social captions, and even signage text for the whole season. You’ll edit and schedule them later, but the blank-page work is done while you’re calm.

Try: “Write a short, warm promotional email and three social captions for my [offer] running [dates]. Match a friendly small-business voice, and end each with a clear call to action.”

DON’T FORGET: SHOPPERS ARE ASKING AI WHAT TO BUY

This year, more gift-hunters than ever will ask ChatGPT and AI search for recommendations. Make sure your Google Business Profile is current, your holiday hours are posted early, and your best products or services are described clearly online. When someone asks AI for “a great local gift shop” or “best [your service] near me,” you want to be in the answer.

THE GUARDRAILS

Don’t over-promise on delivery or stock. Build your calendar around what you can actually fulfill during your busiest weeks, or you’ll trade a good season for bad reviews.

Keep your voice human. AI drafts fast, but holiday shoppers respond to warmth and story. Read every piece out loud and add the personal touch only you can.

Schedule, then breathe. The goal of planning now is to enjoy December instead of drowning in it.

YOUR ACTION PLAN THIS WEEK

Spend one hour: build the calendar with the prompt above, pick your two or three offers, and draft your first promo email. That’s it. You’ll be a month ahead of nearly every competitor in your area — and you’ll thank yourself when the rush hits.

Know another owner who “always means to plan earlier”? Forward this to them today. A one-hour head start in September is worth thousands in December.

Talk soon,

Dave

The AI Playbook