business holiday planning

The Importance of Early Holiday Planning for Small Business Owners

The seasons are a bit different here in Florida. In September, temperatures are still climbing, the sun is shining, and there are at least a few more beach days in our future. But, as a business owner, it’s time to shift gears and start your holiday planning. Yes, I know, pumpkin spice season has barely even started, but it may surprise you to learn that many savvy marketers started working on their holiday strategies in July and August.

Seem crazy? Maybe a little, but getting an early start is the best way to make sure you get the most out of the holiday shopping frenzy. Multiple surveys have found that consumers are likely to be a bit more cost-conscious this year, which could mean that many will hit the stores early in search of pre-holiday sales.

This year in particular, shop owners need to keep in mind that the early bird gets the worm – and in this case, the “worm” is lots of extra holiday revenue! In fact, it’s estimated that a shocking 57% of shoppers aim to wrap up their holiday shopping before December 1st – so if you’re not ready early, you stand to really miss out.

Ready to get a jump on the season? Here’s what you need to know…

When Should Business Owners Start Their Holiday Planning?

When you’re busy running your business, it’s easy to lose track of time. Yet, with the holiday season being the most profitable time of year for many business owners, it’s crucial to stay ahead of the curve.

By September, you should already be deep in the trenches of holiday planning. Why? Because by this point, many of your competitors are already fine-tuning their holiday campaigns and stocking their shelves with holiday inventory.

While time is of the essence, don’t lose sleep over your late start. If you jump in now – or even in October – you’ll still be fine. You just won’t have as much time for leisurely planning as those who got an early start.

So, take a deep breath, and let’s dive right in.

Start with Your Overall Strategy

Now that you know how important it is to get a jump on your holiday planning, it’s tempting to turn your focus to the fun stuff, like designing holiday ads and buying festive decorations … but not so fast. First, you need to get a solid grasp on your overall strategy.

Before you do anything, start thinking about these important points. Take out a pen and paper, and start jotting down some notes. In the next section, we’ll talk about how to execute your plan.

  1. Brainstorm Holiday Promotion Ideas: Start your planning by brainstorming some special deals or offers you’re willing to bring to the table. Whether it’s a buy-one-get-one-free offer, a percentage off, or even a gift with purchase, think about the offers that align with your brand and are likely to attract your target buyers.
  2. Define Your Target Audience and Timing: Think about who you’re aiming to reach and when. Is it the early birds in September or the last-minute shoppers in December? Maybe it’s both! Decide on the optimal moments to captivate your audience.
  3. Carve Out Your Key Messages: What sentiments or messages do you wish to radiate this holiday season? Maybe it’s gratitude, togetherness, or bringing a bit of calm to the holiday festivities. Maybe your brand is more suited to joyful celebrations, no-nonsense advice, or something in between. Whatever it is, make sure your messaging is genuine and aligns with your brand’s identity.
  4. Strategize Your Marketing Tactics: From email blasts and influencer marketing to social campaigns, in-person events, or daily deals, there are plenty of channels and tactics you can explore. Take some time to think about which ones are most likely to give you the best bang for your buck.

Do us both a favor and don’t skip this step. Starting your holiday prep without a game plan is like trying to put together a piece of furniture without directions. Sure, it’s do-able, but it’s frustrating! Whether you spend hours planning every detail or 10 minutes creating a rough draft, having an idea of the direction you’re going will make the rest of the process so much easier.

7 Steps to Kickstart Your Holiday Prep

Now that you have a general idea of who you want to target and how you want to present your brand this holiday season, it’s time to put your ideas into action. Start with these crucial steps.


Start by pulling out your calendar and putting in the exact dates for when you plan to roll out your holiday marketing campaigns. Next, use the data you’ve collected over the year to segment your audience and develop targeted campaigns for each group. When it comes to holiday marketing, targeting is your friend. Tailoring your marketing messages to your audience might seem like Marketing 101, but you’d be surprised how many overlook it.

Once you have your plan and deadlines in place, you can also start creating your social media graphics and posts. Use a tool like Buffer to schedule the bulk of your holiday posts now. You’ll want to leave some space so you have room for spontaneity, but scheduling your core posts now will help ensure you don’t miss any opportunities and allow you to focus on more important things during the holidays.

2. Review Your Inventory Needs

Inventory management isn’t sexy, but it’s vital. You don’t want to be that business that runs out of the hottest item two days into December. Check last year’s data, analyze current trends, and get a read on what people will want this season. Don’t forget to mark your vendors’ ordering deadlines on a calendar you look at daily. Missing these dates could lead to a real problem.

3. Get Your Financial Ducks in a Row

Cash is king, especially during the holiday rush. Put yourself in a good position now by projecting your holiday expenditures for additional staff, more inventory, and ramped-up marketing. Balance this against your expected revenue so you’re not just spending but investing. Get your books straight, make sure all pending payments are in, and maybe think about securing a credit line for emergencies.

4. Strengthen Your Supplier Relationships

Remember that you’re not the only one under holiday stress – your suppliers are too. Early orders not only ensure on-time deliveries but can also land you better prices. Also, make contingency plans for potential supply chain disruptions. In many cases, it’s better to have items and not need them than need items and not have them.

5. Get Your Staff Ready

Hiring temporary staff or upskilling your current team is not something you want to leave until the last minute. Make holiday schedules in advance and clearly communicate your expectations to your team. The holidays can be a busy time for everyone, so set a fairly early deadline for staff to request any holiday time off. This will ensure you can plan your schedules accordingly.

6. Update Your Website and Technology

It’s likely that more people will visit your website during the holidays than at any other time during the year. Make sure your site can handle the uptick in traffic and that the user experience is on point. If you’re not the tech type, now is the time to get an expert’s eyes on your website. Depending on your available time and budget, you may also consider making some tweaks to make it easier to showcase your holiday promotions.

7. Tap Into a Wider Range of Holiday Markets

The holiday season isn’t just Christmas and New Year’s. Depending on your target audience, you may be able to tap into other festive holidays, from Hanukkah to Kwanzaa. Starting early also means that you can start generating excitement for earlier holidays, like Halloween, Thanksgiving, and Small Business Saturday.

Remember, while it might seem overwhelming at first, a structured approach to holiday planning can be the difference between chaos and a successful season.

Following these steps will set you on the right path, but there’s still a lot more to do! Make this holiday season your best ever, with my FREE ebook, “The Ultimate Holiday Marketing Guide for Small Business Owners.”

It’s packed with actionable tips, like:

🌟 How to craft irresistible holiday deals
🌟 How to make the most out of Black Friday, Small Business Saturday, and Cyber Monday
🌟 How to make the most of your holiday gift card sales
🌟 And more!

Don’t miss out, click below to download your free copy now! 👇

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