Starting to Plan for the Upcoming Holiday Season

The air may still feel like late summer, but if you’re a small business owner, now is the time to turn your attention to the holiday season. While your customers are just starting to think about pumpkins and gift wrap, you should already be strategizing. Why? Because the businesses that win the holiday rush aren’t the ones who react—they’re the ones who plan ahead.

The fourth quarter of the year represents the biggest revenue opportunity for most businesses, both in e-commerce and brick-and-mortar. But with rising competition, tighter ad costs, and shifting consumer behavior, it takes more than throwing up a few holiday decorations and crossing your fingers. To make the most of the season, you need a clear plan—and that starts right now.

Start With Last Year’s Lessons

Before looking forward, take a moment to look back. What worked well during last year’s holiday season? What flopped? Did you run out of inventory? Was your website traffic high but conversions low? Reviewing your past performance helps you identify where to double down and where to pivot. Pull reports on sales, ad campaigns, email performance, and customer feedback. Data is your most honest advisor.

Define Your Holiday Goals Now

Are you aiming to increase overall sales, attract new customers, or clear out inventory? Different goals require different strategies. For example, if your goal is customer acquisition, you might offer lower-cost gift items to introduce new buyers to your brand. If you want higher revenue per order, you could focus on bundles or upsells. Be specific. “Sell more” is not a strategy. “Increase average order value by 15%” is.

Map Out Your Promotions and Offers Early

Waiting until November to decide on holiday deals is a recipe for stress. Instead, start planning your promotions now—even if you tweak them later. Will you run a Black Friday sale? Offer a gift-with-purchase in December? Host a local holiday pop-up? Write it all down and build a timeline. Planning early ensures you’re not scrambling later—and gives you time to promote your offers properly.

Audit Your Website and Online Store

Before the holiday rush hits, make sure your digital storefront is ready. Is your website mobile-friendly? Are your product descriptions updated and clear? Do your checkout and shipping pages reflect current policies and cut-off dates? You don’t want a last-minute shopper abandoning their cart because your site won’t load on their phone. A seamless shopping experience is a competitive advantage.

Review and Prep Your Inventory

The holidays are not the time to run out of your bestsellers—or be stuck with slow-moving stock. Use your past data and current trends to forecast inventory needs. If you haven’t placed orders yet, now’s the time. Supply chains can be unpredictable, and the earlier you secure what you need, the better. Consider creating holiday-exclusive bundles or limited-edition products to drive urgency and make inventory go further.

Refresh Your Branding for the Season

People are drawn to brands that feel festive and relevant. You don’t need a total rebrand—but subtle changes like holiday-themed product photos, seasonal packaging, or themed social media graphics go a long way. Think cozy, cheerful, and celebratory. It helps your brand feel like part of your customer’s holiday experience—not just another sales pitch.

Create a Holiday Content Calendar

The best holiday marketing campaigns are consistent, not chaotic. Sit down and map out your content for the next few months. What emails will you send? What social media campaigns will you run? Will you use blog posts, reels, or gift guides? Having a content calendar allows you to stay visible without being overwhelming. It also frees you up to focus on operations once things get busy.

Segment Your Email List

Email will be one of your most powerful tools this season—if you use it wisely. Start segmenting your list now. Consider groups like past holiday buyers, high spenders, local customers, or first-time buyers. Tailoring your messages to each group increases engagement and conversions. And don’t forget to warm up your list with value-driven content before hitting them with sales.

Plan for Paid Ads—Even on a Small Budget

Ad costs rise dramatically during the holidays, especially in November and December. That’s why it’s smart to start testing early. Run small-budget ads in September or October to find your best-performing creative and audiences. Then, scale what works during peak season. If your budget is tight, focus on remarketing ads to people who’ve already interacted with your brand—those are your warmest leads.

Don’t Ignore Local Opportunities

If you have a physical location or serve a local market, lean into community-based holiday efforts. Think Small Business Saturday events, craft fairs, or partnerships with local influencers. Offer exclusive in-store promotions, collaborate with nearby businesses, or host a holiday open house. Local marketing feels personal—and that’s exactly what people crave during the holiday season.

Optimize for Last-Minute Shoppers

No matter how much you plan, there will always be procrastinators. Prep now for them. Highlight fast shipping options. Create digital gift cards. Offer “last-minute gift” bundles. Make it easy for those December 22nd shoppers to buy something meaningful without stress. A smooth, fast checkout could be the reason they choose you over someone else.

Train Your Team and Set Expectations

Even if you’re a team of one, you need a plan for handling increased volume. What’s your return policy? How will you respond to customer questions quickly? Do you need extra help packing orders or managing emails? Set expectations with your team now. The smoother your backend runs, the better experience your customers will have—and the more likely they are to return.

Prepare for Post-Holiday Retention

The sale doesn’t end on December 25th. In fact, the real magic happens after. Plan now for how you’ll turn holiday buyers into loyal customers. That might mean a January follow-up email, a thank-you discount, or a loyalty program invitation. Holiday shoppers are often first-timers—don’t let them disappear after the season ends.

Monitor Trends and Stay Agile

Things change fast during the holiday season. Be prepared to adjust your strategy based on what’s working. Maybe a product goes viral. Maybe your audience responds better to behind-the-scenes videos than polished ads. Stay connected to your analytics, keep an eye on competitors, and be ready to pivot. Agility is an asset, especially when paired with a solid plan.

Success is in the Prep

The holiday season can be the most profitable—and most stressful—time of year for small businesses. But it doesn’t have to be chaotic. When you start planning early, you position your business to thrive, not just survive. With the right mix of strategy, creativity, and preparation, you can finish the year strong, serve your customers well, and set the stage for an even better 2026. So grab your calendar, pour a cup of coffee, and get planning—your future self (and your bottom line) will thank you.