How to Survive the Holidays: A Guide for Small Businesses

Custom tissue paper by @stefanieshank

Deeply discounted Halloween decorations and pillow cases brimming with candy can only mean one thing. The countdown to the holidays has already begun. 🎄

For most of us, the impending festive season will bring one of two things: a hectic dash to the year-end finish line, or a slow denouement into an eggnog fuelled standstill. There’s almost no in between. What it means is that the way we have worked and organized ourselves throughout the rest of the year will stop being sustainable. Surviving the holidays is dependent on making a few changes.

Solopreneurs, freelancers, and consultants are often exponentially impacted by this sudden change of pace. It’s up to you as an independent to manage your own workflow, forecast cash flow, and set boundaries to put your mental health first. But how do you plan ahead and avoid surprises?

Here, we’re sharing tips for small businesses and the self-employed for surviving the holiday season and emerging refreshed in the new year.

Ramping up 🚀

If your business makes or sells consumer goods, chances are the holidays mean busier times are coming. Ditto for those working in or supporting industries and clients related to shipping, events, packaging, hospitality, or travel.

Depending on where you are in the world and who your customers are, the next few months are packed with religious holidays, regional celebrations, and shopping events like Black Friday in the U.S. That means the true holiday season started yesterday.

For those specifically selling to consumers, the boost is already in full swing. As pandemic related supply chain issues persist, consumers are ordering early to avoid disappointment. And holiday sales are expected to surge this year, compared to last, as vaccinations are increasing the confidence of consumers to spend on entertainment and at local retailers.

It is possible to stay healthy, keep up with demand, and maintain positive business relationships, even as the holidays crush down on you. If your business is expected to ramp up over the next month, follow these dos and don'ts to survive the holiday rush:

1. Do set boundaries ✅

As your work heats up, your delivery times might be extended and your response time to emails may increase. Prepare your clients or customers in advance by setting expectations. If you deal with clients, don’t take on more work that you can reasonably handle — an upfront “no” is better than work delivered late.

2. Do ask for help ✅

Hiring seasonal staff can lessen the load and help you maintain a service expectation that you’ve set with customers or clients through the rest of the year. Training and hiring can actually increase your workload up front, but will benefit you in the long run. Hire help for tasks that are easy to delegate and teach. If your budget doesn’t allow for hiring, a virtual assistant is a lower cost way to unburden yourself from mundane tasks.

3. Don’t overpromise ❌

If you run a business selling consumer goods, be clear on your website or in your communications around shipping cut offs for holiday delivery. Linking this info in a prominent banner on your home page or moving it to the top of your FAQs will help alleviate disappointment. You may also add “low stock” tags to popular items so that sold out items aren’t a surprise.

4. Do take breaks ✅

Even if you feel like you can’t afford the time, taking breaks will help avoid burnout. You can’t take care of your business and your clients if you don’t take care of yourself. To set expectations and build in moments of rest, set and clearly communicate closures (if you run a store) or offline days. Can’t afford a day off? Block 30 minutes a day in your calendar to step away from work to take a walk, meditate, work out, or engage in a hobby.

5. Do be mindful of supplier and shipping delays ✅

While you are setting expectations with your own clients and customers, be aware that your suppliers may similarly be experiencing a surge in demand. If it's not clearly communicated, be sure to connect with suppliers to understand cut-off order dates.

💡 Pro Tip: if you’re ordering holiday-specific designs for your custom noissue cards, stickers, or bags, be sure you’re submitting designs in accordance with printing and shipping timelines.

6. Don’t give into the pressure to discount ❌

Popular shopping holidays like Black Friday and Cyber Monday bring with them the expectation to provide discounts. For some brands, this just isn’t realistic. If your margins are already tight or your brand doesn’t align with a discount strategy, you don’t need to participate. Some brands choose to communicate their reasons to customers, educating them on the cost of ethical manufacturing. Others may choose to participate in different ways, like donating to charity with every purchase.

7. Do let yourself get swept up in the spirit ✅

Being busy doesn’t mean being “bah humbug.” Let the spirit of the festivities motivate and energize you. Decorating your space or store, surprising your clients and customers with holiday extras, or hosting events can all help lift your spirits even in the face of a mountain of work. Surviving the holidays is as much about time management as it is about mindset.

💡Pro Tip: Read about how you can add some holiday cheer to your graphic design and packaging.

8. Do fortify your customer service strategy ✅

Regardless of your business, if you’re in a ramping up phase over the holidays, incoming communication will increase along with it. Rising tensions from clients waiting for seasonal work or customers ordering last-minute gifts mean that your customer service needs to be on point. Consider a VA, chatbot app, or part-time staff to ease the burden of customer service demand. Email auto-replies that clearly state response time can also lessen frustration.

Winding down 🐢

For some of you, the incoming festivities mean that your business slows way down. That can be a double-edged sword for some small business owners. If you’re accustomed to fairly reliable income each month over the rest of the year, the impending dip might deliver a blow—especially as expenses for gifts, travel, and events heat up.

A cooling down period may affect freelancers whose clients include large companies with seasonal office shut downs or large numbers of salaried employees taking time off. It also may impact seasonal businesses that rely on specific weather conditions.

For those with a few holidays under their belts, forecasting for seasonal changes has likely become common practice. But if you’re new to the ebbs and flows of self-employment income and haven’t been able to pad your rainy day fund, don’t fret. This is a learning year for you.

On the positive side, the end of year slow down can be a welcome change of pace for those going it solo. It’s a time for rest, reflection, and self-care. And, you’ll have plenty of time to plan and forecast for the coming year. This is your holiday survival guide to the dos and don’ts of managing the cool down:

1. Do tackle your checklist ✅

Remember that one thing you kept putting off? That never endling to-do list that seems to accumulate tasks faster than you can cross them off? Now is your time to shine. While it’s very important to get rest during the break, set yourself up for an easy transition back into work mode by clearing out those low-stakes but necessary admin tasks.

2. Don’t forget to say thank you ❌

If the first part of the year lacked the space for proper gratitude, make up for it now that you have the time to do so. Acknowledging your best clients, customers, suppliers, and other folks that help make you successful means that you have a reason to reach out even when you’re not officially doing business. You’ll also stay top of mind when those same folks are ready to spend money again.

Send branded thank you cards or gifts, host a pandemic-safe gathering or virtual event, or just reach out with some heartfelt words.

3. Do prepare for tax season ✅

Tax time will creep up on you quickly, especially after you hit the ground running in January. Use the slow down period to gather receipts, meet with your investment advisor or accountant, and investigate where else you can minimize taxes owed before the end of the year.

4. Do plan and forecast for next year ✅

If the slow down took you by surprise, now is the time to look back at your year to examine how you can better manage it next time. Are there ways that you can maximize your busiest months by taking on more work? Do you have a plan to sock away a certain percentage of your earnings to cover the lulls? Can you expand your service or product offering to add more revenue in slower months?

This slow down period may also be the right time to generate new leads and contacts for business in the new year: cold emails to potential clients, experimenting with marketing to reach new audiences, or attending networking events.

5. Do clean house ✅

In the same way that spring cleaning airs out a musty house in time for summer, a good holiday reckoning of your business can leave you breathing fresh air come the new year. Physically declutter your workspace, clear out your email inbox, and take a hard look at your processes and workflows. Are there ways to simplify?

6. Don’t worry about logging off ❌

If your work slows to a drip during this time of year, is it worth keeping the lights on for the odd email here and there? Establish some actual office or store closure dates and communicate them clearly and in advance. Set your “out of office” reply, update your socials, and unplug. It’s not unusual for other businesses to close down for the holidays—if you can afford it, take a guilt-free break.

💡 Pro Tip: Parents are masters of prioritization and time management—get advice for both from a founder and dad.

Final thoughts

No matter what industry you’re in or which holidays you observe, there is something magical about the season that unites us all. For every small business owner — ramping up or winding down — take advantage of the end of year vibes with these three universal tips for surviving and thriving during the holidays:

1. Do inject fun. Busy or not, access your inner child and embrace nostalgia and wonder.
2. Do acquire some good karma. Give back, if you can, with time, percentage of profits, or cash donations to causes of your choice.
3. Do reflect on the year — and focus on your wins. You made it! Be proud of what you’ve created all on your own. Bask in even the tiniest of successes.