If you’re approaching your first holiday season as a brick and mortar store owner or you need a little help preparing for the busy season, consider this your mini small business guide for holiday planning!

I know, I know it’s January!  Why are we talking about the holidays when Q4 just ended? For seasoned retailers, working way ahead of seasons is probably the norm.  But for new retailers, I often hear questions like “When should I order holiday merchandise?, When should I start getting ready for the holiday season? or When should I bring out holiday merchandise?”

A Retailer's Guide For Holiday Planning


Ideally, this should be done at the beginning of each year (or even earlier – some retailers order one full year ahead).  You can schedule deliveries for July and later, but here are a couple of tips regarding holiday orders with wholesale suppliers and vendors.

  • Attend a Market Event, like AmericasMart in January. You’ll be able to spot trends early on in the year and place orders.
  • Have your orders shipped as early as possible.  Even though you place an actual order for holiday merchandise early in the year, if you don’t also schedule your shipments early, you might miss out on merchandise.  Retailers who schedule shipments first, get first dibs at merchandise. If you wait to have your order shipped late in the Fall, the vendor may run out of certain items and you’ll miss out.

But don’t worry if you are a new retailer and you aren’t in the position to do this, you can still order throughout the year.  I just recommend ordering as soon as you possibly can. Click here to read a blog post I wrote about the evolution of our ordering process. 


Take the time to plan and design the overall concept of your holiday window displays. If you can come up with a theme and design idea early in the year, then you can order supplies and design elements from one of the Markets you attend (AmericasMart, Dallas, Vegas).

You can also visit wholesale websites and order what you need throughout the year.  Buying your window display design elements at wholesale prices can save you hundreds of dollars each year and these can be sold after you use them!


You may do this earlier in the year and if you do, great!  But if you’re new and not planning well in advance yet, then simply grab a calendar and start mapping it out!  

Whether you use a paper calendar, a digital calendar, or special online organizational software like Trello, it’s important to start planning the what and when.

If you want to make it easy, print out a single sheet calendar for October, November, and December.

On the calendar, you’ll want to include in-store events, promotions, social media posts, and Holidays. Make sure to add other important retail dates like Black Friday, Small Business Saturday, and Cyber Monday.

Canva is my favorite tool for creating marketing content!

Don’t forget to add a date to your calendar as a reminder to update any special store hours on your website, Yelp, Google My Business listings, social media accounts, etc.  If you change your store hours for the Holidays, be sure to communicate this everywhere possible so your customers can find that information easily. Don’t leave them guessing.


If you’re extending your hours and expecting a rush of customers during the holiday season, you will want to hire some help.  Holidays can be exhausting on a personal level, add managing a retail store to the mix, and you can sometimes burn out. In order to avoid this, try to bring in some help so you can take some time off and take care of yourself.  

A great way to find some holiday help is to post on social media that you’re looking to hire temporary employees for the holiday season.  You might be surprised at how many are interested in making a little extra money for gifts!


Think about special touches for your customers. For instance, some retailers will order special holiday bags with decorative tissue paper or offer free wrapping. You’ll want to order these supplies at least 2 months in advance, especially if there’s printing involved.

You’ll also want to have plenty of gift cards on-hand. Order these now so you know you’ll have them in time.

Senses in a store are important.  You can also plan what your music selection will be and what you’ll use to make the store smell like the Holidays. The smell of fresh-baked cookies is one of my personal favorites.  

If you ship items, particularly during the holidays, be sure to have plenty of shipping boxes and envelopes on hand.  You might even order holiday stickers or cards for your online orders. Branding and special touches leave a nice impression with customers.


This is the fun part!  Many retailers will begin this process at the end of October or early November. In 2021, some indie retailers even started in September!

Whenever you choose, be prepared to spend a late evening or a day off to do this.  The more you decorate, the more time you’ll need. In order to save customers from the inconvenience of walking around open boxes and a disorganized space, you might want to consider decorating when the store is closed.  


This one is debatable among many retailers.  You often hear people complain about big box stores bringing out merchandise “way too early” in the year, but the truth is, many shoppers prefer to start their holiday gift shopping early. Some independent retailers start as early as September, yes September!


If you aren’t sure what your customers prefer, run a survey or post a poll on Facebook or Instagram.  The results might surprise you!

My sister and I resisted bringing out holiday merchandise too early in November but after we ran a poll on Facebook we quickly learned the majority of our customers said: “The earlier the better!”


We all know the holiday season can be overwhelming, but as a retailer, if you take the time to plan throughout the year, it will be so much easier to handle.  

Do you have a good tip for small business holiday planning? Do you plan for Q4 a little differently?  Comment below and let us know – every bit helps!

If you want MORE valuable information like this, listen to the Savvy Shopkeeper Retail Podcast and visit the Shopkeeper’s Academy where I share even more information in our group memberships!

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