Can we make a confession? As a small business owner, the holidays are a really tough time!

It’s no secret that the period of time between Thanksgiving and Christmas is the biggest retail sales season of the year. As a full-time small business owner that relies on holiday sales to account for a large percentage of annual income, there’s a lot of pressure to “get the holidays right.”

We’re not going to lie, we’ve had a few extra glasses of wine thinking about competing with retail giants for your hard earned holiday spending cash. And while we’re thankful that more and more consumers are subscribing to the Small Business movement to support little shops like ours, it’s a constant struggle to prepare for, and execute, the “perfect” holiday sales season.

We’re experts by no means, but we have learned a few things (the hard way;)) about how to boost your holiday sales. See below for a roundup of our tried and true holiday sales tips that have helped us through this wonderfully chaotic time.

Holiday Sales Tips for Small Business Owners

  • Plan Ahead. Here’s the scenario: You’re sailing along doing your thing. You look at the calendar. It’s November 25th. You realize Thanksgiving is impending. You freak out – S.O.S.! You make a 10 page to do list and vow not to sleep until every last agenda item is checked off. Sound familiar? You’re not alone. The single best tip we can give you for staying afloat during the holidays is to NOT wait until the holidays to start preparing for the holidays. Make inventory lists ahead of time, and have products in stock well before you’ll need them. Update your social media pages, prepare graphics, plan shop sales, photograph new products, etc. weeks (if not months) in advance of November, so you can charge full steam ahead into the holidays, without worrying about how many life vests you have on the ship. Youknowwhatwemean? Be prepared, and life will be so much easier!
  • Narrow Your Focus. With so much going on during the holiday season, it’s really, really easy to lose track of the task at hand. One moment you’re packaging up 50 holiday Etsy orders, then the phone rings and you chat with your mom for 30 minutes, hop online and answer a few dozen emails, research some new merch, and return to your packing task 2.5 hours later only to realize you have no idea which items are in each of your identical packages. We definitely relate to this one! During the holidays, it’s crucial to tackle your to do list one task at a time, with no distractions in between (even if they’re productive distractions). Try this now, and thank us later!
  • Surprise and Delight. One way you can amp your holiday sales is by surprising and delighting your customers. It’s one of the ways a small business can stand out from its national chain competitors, and allows you to reinforce the reason you love being a small business owner so much! Whether it’s something simple (like including a hand written thank you note with each order placed) or something more elaborate, it’s important to thank your customers for helping support your dream. (Bonus: One way we’ve helped directly boost sales is by surprising our social media followers with exclusive sneak peaks of new products! It provides valuable user feedback on what people like, lets the anticipation for new products build, and is all around fun!)
  • Communicate with Your Customers. This one is crucial to surviving the holiday sales season. Establishing clear and direct communication between your prospective customers, current customers and your business is one of the most important things you can do. One easy way to start is by creating a shop FAQ page to anticipate customer questions. This will save you loads of time answering emails during times when you are stretched thin. Payment and shop policies, ordering process instructions, shipping timetables, holiday ordering deadlines, promotional coupon codes, etc. are some of the most common questions that we receive, and make a great place to start!
  • Don’t forget to celebrate. It’s the holidays for you too, y’know! Taking some time off (even just a weekend) to spend with your loved ones will help you be refreshed and ready to tackle the new year. Planning a trip (as opposed to just taking a weekend for yourself) gives you the added benefit of something to look forward to on those long nights of work, but at the very least you deserve a bit of R&R at home.
  • Digest & Document. A really important piece of a small business holiday sales strategy comes after the holidays are over. When the rush settles down, take time to document processes and measure successes and failures. Each year, you’ll get closer and closer to building yourself a roadmap that works for you, and each passing holiday season will be less of a guessing game and more of a “you got this!” game.
  • Forgive yourself. As well intentioned as we can be, sometimes things don’t always go as planned. While having goals and focus is important, it’s equally as important to give yourself a break if you didn’t get as much done as you wanted to this year. Owning a small business is a labor of love, and the hard parts make the wins that much sweeter!

We hope you found these holiday tips helpful. If you have any helpful tips we left off the list, we’d love to hear from you! Give us a holler at or add them to the comments below.