The holiday season is one of the most important—and potentially profitable—times of year for small businesses. Whether you sell products, offer services, or run events, preparation is key to maximizing revenue, reducing stress, and creating meaningful connections with your customers.

To help you get ahead, we’ve put together practical strategies to guide your holiday planning.

Here’s how to prepare your small business for a successful holiday season:

1. Start Early: Planning Now Saves Time Later

Early preparation allows you to:

• Stay ahead of supply delays

• Build intentional marketing campaigns

• Prevent last-minute stress

• Deliver a polished customer experience

Before planning anything new, review last year’s performance:

• What worked well?

• What didn’t?

• Which products or services were most popular?

• What challenges did you face?

This helps you make data-backed decisions instead of guessing.

2. Create Your Holiday Marketing Strategy

The holidays are a peak season for visibility—but also for noise. A strong marketing plan keeps your message clear and compelling.

Key strategies to consider:

• Holiday Promotions: bundles, early-bird specials, VIP sales, gift cards, or limited-time offerings

• Seasonal Branding: update your website banner, social profiles, and email graphics

• Content Calendar: pre-schedule holiday emails, reels, posts, and stories

• Partnerships: collaborate with complementary businesses to extend your reach

• Engagement: run polls, giveaways, or community-centered campaigns

Your messaging should speak to the season’s mindset: convenience, gifting, appreciation, and celebration.

3. Prep Your Operations & Logistics

The operational side can make or break your holiday season.

Check your:

• Inventory: reorder top sellers early

• Supplies: packaging, shipping materials, branded inserts, or holiday extras

• Staffing & Scheduling: adjust hours, build coverage, and set communication expectations

• Shipping Deadlines: clearly communicate cut-offs on your website and social platforms

If you work in services, consider:

• Offering holiday bundles

• Extending appointment availability

• Creating a waitlist system

• Automating reminders

Small adjustments now prevent big problems later.

4. Elevate the Customer Experience

Even small touches can create memorable experiences customers rave about.

Consider adding:

• Gift-wrapping

• Handwritten thank-you notes

• Holiday-themed packaging

• Loyalty rewards for repeat purchases

• A customer appreciation event or discount

Acts of gratitude go a long way—especially during the busiest season of the year.

5. Mind Your Well-Being (Seriously)

The holidays can be overwhelming for business owners, especially women who are often managing both business and family responsibilities.

Protect your energy by:

• Blocking personal/family time in advance

• Delegating tasks where possible

• Automating processes

• Pre-scheduling content and communications

• Setting boundaries with your calendar

A joyful business owner creates a joyful customer experience.

6. A Simple Holiday Prep Checklist

Here’s a quick version your members can save:

✔️ Plan Ahead

• Review last year's performance

• Set goals for this season

✔️ Marketing

• Define promotions and offers

• Schedule social and email content

✔️ Operations

• Check inventory

• Prepare staffing and schedules

✔️ Customer Experience

• Add seasonal branding

• Plan a customer appreciation touch

✔️ Self-Care

• Block personal time

• Delegate/automate tasks

Final Thoughts

The holiday season doesn’t have to feel chaotic—with early planning, thoughtful marketing, and attention to customer experience, your business can finish the year strong.

And if you need support designing an unforgettable holiday event or branded experience, Anne Urban, with Destination Planning Corporation, is an excellent resource within our membership community.

Stay organized, stay intentional, and cheers to your most successful holiday season yet!