Nine Things You Can Do Right Now to Prep for Holiday Business

In my inbox in early September there was an email with the subject line “Get Prepared for Holiday Orders.” I laughed, then immediately thought to myself, “I’m already behind.”

I am the kind of person who dislikes seeing “Back to School” sections when summer has barely started. I get annoyed when stores set up holiday displays before we’ve even gotten to Halloween (this already happened to me last week, and no matter how much cheer the branded coffee mugs were offering me, I wasn’t having any of it). And while I love the soundtrack for “A Charlie Brown Christmas,” I do not want to listen to it until after Thanksgiving. These consumer trends keep us from existing in the present. They keep our sights set on a future moment that we can buy things for instead of appreciating what’s in front of us.

But when you’re running a business, if you don’t start thinking about the holidays in advance, it’s easy to feel like you’re scrambling when the busy season rolls around. I have a friend who runs a brick-and-mortar store that I often collaborate with, and we joke that the best time to prep for the holidays is probably January. In fact, without any boundaries or established workflows, you could probably always be in holiday prep mode all year round.

There are a lot of “shoulds” this time of year, and it’s easy to get wrapped up in what we haven’t done or what we already feel behind on. I connected with Heather Leeflang of H Works, and much like myself, she felt that there was so much on her “should” list. In fact she immediately pointed out that she had a solid list of things that she wanted to do for holiday prep, but hadn’t implemented yet. “I need to block out time and approach that time with intention, purpose, and intensity,” says Leeflang. “Really, as I go through the list of things that would be most effective toward achieving my goals, scheduling specific tasks for specific times (ahead of time) and then sticking to those plans would truly be the most productive holiday planning tip I would offer myself.”

With that in mind, we’re going to take a look at some of the things that we can do right now to make those plans a little more achievable and manageable. Holiday prep is going to look different for every business, but these will hopefully help to set the groundwork for a season that’s a little less frantic.

Make a calendar and timeline

The best thing to avoid last minute stress is to sit down right now and figure out what the coming weeks and months look like. This will allow you to set deadlines and your own expectations of what you are going to get done. “I like to back-engineer a timeline for the holidays,” says Sarah Black of Made. “All customers’ orders delivered 1 week before Christmas, 1 week for delivery, and 2 weeks to make made-to-order items. So already, I’m cutting off made-to-order items right after Thanksgiving.”

That’s specific to her business, so your own calendar and timeline may look different, but it’s essential to keep in mind things like production time and shipping deadlines. You may want to work from a sample timeline and build it out according to your own business needs. Leeflang noted that one of her goals for holiday prep is to print out a physical daily calendar and plan out the whole season on paper. That can give you a good visual reminder in or near your workspace of where you’re at and what you want to be working on.

Analyze the numbers

On the backend in your Big Cartel shop, look at holiday sales and profits from previous years. Compare the last few years to see when your biggest sales months were. This can help you to set your expectations on what you’re going to do, as well as some goals and intentions for what is achievable this coming holiday season. It also helps you to have a better idea of what you need to order in terms of product inventory, packing materials, and shipping supplies.

Check in with your community

Don’t be afraid to ask people what they want. October in particular is a good time for doing that, because you still have a little time to make changes according to feedback. “During the holidays I have the question, ‘what am I going to focus on and make this year?!’” says Black. “So I utilize Instagram surveys and polls to find out from my customers what type of products they are looking to give others or buy for themselves this holiday.” Invest a little time in social media or even a newsletter to find out exactly what people want from you.

Ask yourself what you like as a customer

A lot of the time, we’re thinking about how to get our products out there. But it’s also important to take a step back and think about how you function as a consumer during the holidays. How do you like to be communicated to? Do you feel inundated with holiday sale newsletters? What are some of the things that your favorite brands or shops do well that you want to emulate?

Be realistic about what you’re going to do

It’s easy to get into the frenzy of holiday business, particularly as you start to see other creatives and small businesses around you going into full blown holiday mode. You can help with some of that by setting your expectations now and sticking to them. Working through a calendar and timeline and checking in with your customers about what they’re excited about can help you do that. But we also have to figure out our own limits. Take some time to ask yourself some serious questions:

  • What are you capable of doing this year?
  • What do you need out of this season financially?
  • How much do you want to do?

This might be a season when you’re looking forward to launching a bunch of new things, or maybe you’ve realized after a few holiday seasons that you actually need to scale back instead. When it comes to business, there’s no one right way to approach this time of year, and as an independent creative it’s important to know and trust yourself.

Stock up

Once you’ve figured out your timeline and what you’re committing to offering, now is the time to stock up on things like packaging and shipping supplies. It’s a good time to consider if there are additional things you want to include in your holiday orders, like a postcard or a sticker. Allow yourself to be creative here, which helps to keep things more fun.

Figure out how you want to do sales and discounts

Discounts aren’t for everyone, but Black pointed out that one of the pieces of advice she wished she had earlier in her career is that “most customers are expecting a discount code, even from us homemade shops.” Black notes that while it might mean a lower profit margin on each item, overall, “it usually means more orders.” This doesn’t necessarily mean that you need to take an enormous cut in profits. “Make smaller or simplified products that still provide you with the same profit margin ratio as your larger or higher priced items. These always sell well for me,” says Black.

Make it special

In my own holiday orders I usually include a special, small watercolor bookmark that I make in big batches. The process of sitting down to work on that feels meditative and it adds a special element to seasonal orders. You can also use other things to get you in the holiday mood, like lighting a scented candle while you’re working to make things feel more festive, even if you aren’t.

Take care of yourself

“I think the main thing to remember is to put yourself first,” says Black. “Don’t exhaust yourself trying to meet every expectation of customers and keep up with other brands. You have full control and can—and should—plan your business holiday schedule around your personal holiday schedule. Decide what your boundaries/limits are and clearly communicate timelines with your audience.” Another essential part of taking care of yourself is ensuring that you’re enjoying at least some of the process. “Make it fun,” says Black, “for your customers and for yourself!”

Anna Brones

Writer and artist based in the Pacific Northwest. Author of several books including Fika: The Art of the Swedish Coffee Break. Works as a papercut illustrator and teaches classes and workshops on art and creativity. Find her online at

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