11 Smart Holiday Strategies Small Businesses Can’t Skip This Year

On average, the holiday period can represent between 25–40% of annual sales for many small businesses (National Retail Federation), and customers are starting their shopping earlier than ever, some as early as August. That means the work you put in now will directly shape how you finish 2025.

Based on industry projections, the 2025 holiday season is shaping up to be a tight one. Holiday sales are projected to grow just 1.2% year-over-year, well below the broader annual retail growth rate of 2.7–3.7% (Deloitte, NRF). Customers remain cautious, price-conscious, and selective about where and how they spend.

This is not an ideal situation, and there’s little we can do to immediately change the macro environment, but there are steps we can take to navigate this season as strategically as possible. Here are 12 insights—grounded in market data and trends—that will help you plan, execute, and get the most out of this holiday season.

1. Set Realistic Goals

With slower projected growth, it’s critical to base your holiday sales targets on conservative projections. Think about your performance from last year: if your product assortment hasn’t significantly expanded or you don’t have a major new launch planned, it’s smart to use the industry’s 1.2% growth projection as your baseline.

Action:

• Focus on protecting your margins and maintaining cash flow. Every discount you offer should be intentional and sustainable. Use tools like 37 Oaks Pricing Calculators to evaluate how each promotion impacts profitability.

• Build “best case” and “worst case” plans so you can adjust quickly if sales are higher or lower than expected. For example, know in advance what levers you’ll pull if you’re at 80% of your goal mid-December, so you’re not scrambling at the last minute.

2. Prioritize Value Offers

Customers are prioritizing affordability and practicality. Bundles, multi-purpose products, and “under $25 or $50” gift options resonate strongly with shoppers looking for value.

Action:

• Build holiday assortments that clearly communicate value. Bundled products not only make great gifts but can also increase your average order value.

• Use messaging that tells customers why your products are a smart purchase, whether it’s longevity, quality, or solving a specific problem. Don’t assume customers will connect the dots; spell it out in your product descriptions, emails, and social media captions.

• Where possible, offer flexible payment options (e.g., Buy Now Pay Later) or loyalty discounts. These small gestures can ease purchase anxiety and encourage repeat sales.

3. Share Uplifting Messages

Consumer confidence is low, debt is rising, and prices are higher (U.S. Conference Board Consumer Confidence Index dropped 7 points year-over-year). Add in the natural stress of the holidays, and customers are carrying a heavy load.

Action:

• Connect with your customers’ emotional state. Storytelling that inspires or makes them smile goes a long way in building a connection. Check out the 37 Oaks University Bob & Weave episode on Storytelling That Sells (free to access when you join the free 37 Oaks Community).

• Share behind-the-scenes moments, customer success stories, or simple gift inspiration guides. Not every post has to be about making a sale; focus on building a relationship.

4. Market Early and Often

In our 37 Oaks University Holiday Planning Workshop, we talk about the “holiday creep” trend: customers now expect to see promotions well before Thanksgiving, as they are starting to shop as early as August.

Action:

• Marketing can be overwhelming, so slowly ramp up your holiday campaigns. Launch your first email campaigns in October, then layer in social media posts, paid ads, and other touchpoints as the season progresses.

  
  

• Use a content calendar to maintain consistency from October through your final shipping deadlines. Long gone are the days of creating this on your own, from scratch. Utilize generative AI tools to work smarter and not harder on your marketing efforts. Check out one of our recent blogs to jump-start this process: Uncertain Times, Proven Moves: Small Business Resilience + How AI Makes It Easier

  
  

• Focus on getting the most out of 2–3 key holiday shopping dates, like Black Friday, Small Business Saturday, Cyber Monday, and final shipping days, so you don’t stretch yourself too thin.

5. Attend Local Markets

While e-commerce continues to grow, physical spaces, like storefronts, wholesale accounts, and community pop-ups, still drive the majority of sales in the US.

Action:

• Identify 2–3 in-person selling events that align with your brand and audience.

• Focus on smaller “take-home now” items that customers can easily purchase on impulse.

• Use these events not just to sell but also to collect customer emails and other contact information.

  • Free Resource: Check out the 37 Oaks University Bob & Weave episodes on

    • The Strategy Behind Successful Pop-Up Markets

    • How to Build an Email List

    • 10 Tips for Effective Email Campaigns. 

  • Join the free 37 Oaks Community to access.

    
    

6. Retain Current Customers

Your existing customers will be your biggest asset this holiday season. They spend more per transaction and cost less to reach than new customers.

Action:

• Give loyal customers VIP early access to new products or holiday bundles before the broader holiday rush.

• Use what you already know about them, their purchase history, and preferences, to send personalized emails or texts.

• Reward repeat purchases with loyalty points, perks, or small surprise-and-delight moments.

7. Leverage Social Commerce

Shoppable content on social commerce sites, such as Instagram, TikTok, and Facebook, will drive a significant portion of holiday sales. The average U.S. consumer spends over 2 hours per day on social media, so it only makes sense to meet them where they already are.

Action:

• Turn on shoppable product tags and integrate your e-commerce catalog with your social accounts.

• Host live selling events with product demonstrations, limited-time offers, and Q&A.

• Partner with micro-influencers who can authentically share your products with their engaged audiences.

Free Resource: Check out the 37 Oaks University Bob & Weave episodes on

• Selling on TikTok Shop

• Content That Converts

• Building Strong Marketing Collaborations

Join the free 37 Oaks Community to access.

8. Use AI Tools

Small business owners can’t do everything on their own, and now, you don’t have to. AI tools can help you plan and implement holiday strategies by forecasting sales, personalizing marketing campaigns, managing inventory, and even creating content.

Action:

• Take advantage of AI features already built into e-commerce platforms or your email marketing tools.

• Automate time-consuming tasks like abandoned cart emails, product recommendations, and customer segmentation.

• Review your data weekly or bi-weekly and make adjustments in real time based on sales trends.

9. Mitigate Tariff Risks

Tariffs on imported goods, especially popular holiday items like toys and decorations, are increasing costs by up to 20% (AP News).

Action:

• Diversifying your suppliers to reduce your risk of delays or price shocks is a good first step. Building relationships with U.S.-based or regional suppliers can help.

• Stock up early on high-demand products so you’re not left scrambling during peak season.

• If you need to raise prices, be transparent with customers. Explain the reason behind the increase; many will appreciate the honesty and still purchase.

10. Collect Customer Information

The holiday season is your single biggest opportunity to gather customer data and insights. 73% of small, retail-centric businesses generate about 25% of annual sales in November and December. This could mean that it is also when you get the most traffic to your business. Great time to get the most out of this, and we don't just mean sales.

Action:

• We said this before, but it is important enough to mention again. Be thoughtful and intentional in collecting customer information such as email addresses for newsletters, phone numbers for text messaging, mailing addresses for direct mailers, and/or social media handles for online engagement.

  Have tools in place (at events and online) to capture customer emails and preferences. Incentivize sign-ups with discounts or small perks. Use this data to refine next year’s product line, pricing strategy, and marketing campaigns.

11. Close the Year Intentionally

Rather than stumbling into January, set aside time now to plan your close-of-year priorities.

Action:

• Set up a schedule to plan to review your weekly or bi-weekly performance so you can make changes before it’s too late.

  
  

• Schedule a post-holiday debrief or recap in January to capture lessons learned while they’re still fresh. This will help you set up measurable goals for 2026 that build on the momentum and relationships you’ve created.

  
  

• Each year, the 37 Oaks Growth Lab dedicates January and February to annual planning strategies, tactics, and support. Tap into coaching, courses, tools, resources, and community.

Final Thoughts

The holiday season can make or break the year for many small businesses, and the stakes feel especially high in 2025. While the economic climate may be challenging, success doesn’t hinge on perfect conditions; it comes from thoughtful planning, strategic execution, and the ability to adapt as you go. By focusing on the strategies above, you can position your business to maximize sales, strengthen customer relationships, and set the stage for a powerful start to 2026.

Remember, every email captured, every loyal customer nurtured, and every data point collected this season will serve as building blocks for your next stage of growth. Start early, stay consistent, and use this holiday period not just as a sales opportunity, but as a launchpad for the future.

Terrand Smith

Founder/CEO

37 Oaks

Who is 37 Oaks?

37 Oaks is an education company that strengthens communities by transforming small businesses into valuable, commerce-driven assets.  Our goal is to empower them through Commerce, Innovation, and Strategy.

Join The 37 Oaks' Newsletter.