Every year, the holidays catch businesses off guard with how fast they seem to creep up. One week, you see yourself saying “we’ve got time.” The next, somebody’s scrambling to throw together a Black Friday offer, three emails, a social graphic, and a discount code thrown together in a panic. The problem isn’t a lack of effort. It’s that the holiday sneaks up fast, so the marketing starts late.

This week’s newsletter is simple: stop thinking about the holidays as a handful of promotions and start thinking about them as a 90-day revenue plan. When you know what you’re selling, who you’re selling it to, when you talk about it, and what happens after, the holidays stop feeling so chaotic and start feeling a lot more profitable.

Think of your holiday marketing in three simple phases: Warm Up, Convert, and Extend.

The Warm Up phase is where you get people paying attention before you ask them to buy. Share customer wins. Talk about the problems your offer solves. Answer common objections. Build anticipation. If your first holiday message is “25% OFF TODAY,” you’re asking people to make a fast decision with no runway. Give them a reason to care before you give them a reason to buy.

Then comes Convert. This is your main promotional window, and the goal is not to create twelve different offers. Pick one strong offer and make it easy to understand. Your customer should immediately know what it is, why it matters, and why they should act now. That might be a discount, but it could also be a bundle, bonus, upgrade, limited package, gift card, or priority access.

Finally, Extend. This is where most businesses leave money on the table. Your campaign doesn’t have to die when Black Friday ends. Follow up with non-buyers. Thank and upsell new customers. Push gift options. Promote year-end deadlines. Pre-sell January. The people who didn’t buy the first time aren’t necessarily saying no. Sometimes they just need a different reason or a different moment.

A simple version of your 90 days might look like this: October builds attention and demand. November drives the primary promotion and follow-up. December focuses on gifting, urgency, year-end opportunities, and January pre-booking. Now instead of waking up every morning wondering what to post, you have a direction.

Lucky for you, AI is great at planning.

Instead of staring at a blank calendar and creating 3 months of marketing from scratch, give AI the details of your business and let it help you build the campaign. The trick is not asking, “Give me some holiday marketing ideas.” That’s how you end up with a list that applies to every business on the planet.

Give AI your audience, offers, price points, channels, deadlines, and goal. The task it to think like a strategist and map the full campaign from warm up to sales to the follow up.

Copy + Paste this prompt

1️⃣ Podcast: BFCM 2026 Planning Guide — The Ecom Scaling Show
A timely listen on planning Q4 before the rush hits. They dig into offers, budgeting, inventory, customer value, and why your holiday strategy should be thinking beyond one big weekend. Perfect companion to this week’s “plan early” mentality.

2️⃣Article: Holiday Ecommerce: 11 Strategies for 2026 — Shopify
This one goes beyond “run a Black Friday sale.” It covers planning ahead, email personalization, loyalty, promotions, customer retention, and turning holiday buyers into customers who stick around after December. Use it to steal a few ideas for your own Warm Up, Convert, and Extend phases.

3️⃣Book: The 1-Page Marketing Plan — Allan Dib
If 90 days of marketing already sounds like it could turn into a 47-tab spreadsheet, read this. Dib’s framework is built around simplifying the entire customer journey onto one page — exactly the mindset you need to turn your holiday marketing into a plan instead of a pile of random promotions.

Done-For-You: Want me to run this play for you? My Buzz Packages are designed for business owners who want expert results without the guesswork. We handle the strategy, the content, and the execution. The Promotion Sprint .

Done-With-You: Need a custom playbook for your specific situation? Book a 1-on-1 Strategy Call with me. We’ll spend an hour building a roadmap tailored to your exact goals. .

Do-It-Yourself: Want the tools to run these plays yourself? The Outlaw AI Toolkit gives you 9 expert-trained AI assistants to handle your marketing in minutes a day.