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Episode 112: How to Prepare Your Small Business to Take Time Off During the Holidays

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The holidays create chaos for everyone—especially small business owners.

And we don’t just mean the stress of putting together holiday sales, campaigns, and everything in between. Instead, we are thinking about something that it is—believe it or not—arguably past time to be thinking about: how to prepare your small business to take time off during the holidays.

In this episode, we are joined by Mary Adkins, Treefrog’s Director of Operations, as she breaks down exactly what you and your team need to do leading up to the holiday season so that you can actually take time off and enjoy this special time of year with loved ones.


Tips on How to Prepare Your Small Business to Take Time Off During the Holidays

At Treefrog, we’ve been taking two weeks off for the holiday season for about a decade now. It’s a great way to provide our team with time to spend with family and reset for the upcoming year. However, that break would not be possible without Mary’s organization and planning.

Every small business operates differently, but we want to walk everyone through tips they can use to prepare their teams and clients for an extended break.


Start Planning Early

The first step in preparing to take extended time off is to start early. You need to set a plan—including timelines, communication, and to-do lists—as early as possible. Identify potential issues and bottlenecks and plan around them. We’ve all heard the saying that if you fail to plan, you’re planning to fail, and that’s certainly true here.

By October, Mary has already started working on timelines for clients' projects through the end of the year and into the beginning of the next year. In fact, because of our workload, she always starts planning for our time off starting in or around August. For an agency that’s handling a lot of different types of projects, all with moving parts, we have to start months ahead of time.

However, even if you’re a B2C business or a B2B with simpler project timelines, it’s still good to act early. The consequences of failing to act soon enough could be missed deadlines, burnt-out employees, and miscommunication—all of which negate the purpose of having a break in the first place.


Create Protocols and Checklists

You should already have a checklist of some kind that lists everything that you do on a recurring basis. If not, you should first take the time to develop standard protocols and operating procedures. Then, you should catalog everything that would ordinarily be done during the time that you’ll be on break and figure out how to get it done before you leave, or determine if it can be pushed until after you resume work again.

For example, we write monthly blogs and newsletters for a number of clients. While we normally write them a month ahead of the time they’re posted or sent, when planning for the holiday season, we work ahead. So, by October, we are well into our production of December blogs.


Use a Project Management Software

To make preparing for the holidays as easy as possible, and so you can create timelines for the rest of the year, we highly recommend investing in some kind of project management system. Mary can easily adjust schedules and see all aspects of a project from beginning to end because we use ClickUp.

ClickUp is a project management system that allows us to get a comprehensive picture of our workload, anticipate bottlenecks, and enable our team members to work together to complete each project in an efficient way.

Mary especially loves this software as we prepare for the holidays because it allows her to easily see every team member’s schedule and capacity so that she can assign projects and tasks, and we can work ahead as we prepare for the holidays.

We love ClickUp for small businesses because it can be as simple or robust as you need it to be. Mary chose this software for our company because as we grow, it can grow with us. If you’re looking for a project management system, be sure to check out ClickUp.



Mary’s next tip is to be as efficient as possible and automate what you can. There are so many tools and resources available now that can make your work life easier and save so much time. At Treefrog, we use automation capabilities within ClickUp, HoneyBook (our CRM), and Zapier.

Between different softwares and AI, the automation possibilities are so extensive that they seem endless and can get overwhelming. But, even some simple automations can help make your business exponentially more efficient. If that sounds like too much to handle now, consider simply using the “schedule” or “send later” functions of your email to prepare some communication ahead of time.


Limit New Projects

As you prepare your small business to take time off for the holidays, something else you want to be sure to do is set a cut-off for taking on new projects. Customer experience is so important, and taking on a project you can’t start right away or becoming immediately inaccessible is not the best way to start a relationship.

Plus, pre-loading your other client work means that there’s less room in the schedule to take on new projects.

That said, please know that there is absolutely nothing wrong with telling potential customers, “We can’t fit your project in before the end of the year, but if your timeline allows, we can get you on the schedule for [INSERT DATE HERE.]”

For the sake of offering great customer service, you always want to underpromise, over-deliver, and set expectations that you can actually accommodate.


Hire Extra Help

Another great way to prepare your small business to take time off during the holidays is to hire extra help—even if it’s just temporarily.

If you know you’re trying to front-load some of your work before taking time off, moving some lower-level tasks to virtual assistants or freelancers can free up your staff’s time to focus on the higher-level project execution. While this might seem like an extra cost, your increased output before time off will delight your clients and make the break flow even more smoothly.



With all of that being said, the most important process that a business can set up when planning to take time off is communication.


Inform Clients, Customers, and Vendors

First, if you’re a service-based business, send a personalized message to your current clients in advance. Mary would recommend a month ahead of time for the direct message, and then add more subtle reminders closer to the scheduled time off in your other messaging with them. Communicate what will be going on with their projects before, during, and after the break.

If you have customers as opposed to clients, we recommend sending out an email newsletter far enough ahead of time that they can place their orders and you can fulfill them before the break. Be very explicit about the last date that they can place an order and have it shipped to them within your normal operating timelines AND about when orders that are being placed during the break will be shipped.

Also, don’t forget to communicate with your vendors! To help maintain a good relationship with your vendors, let them know that you’ll be unreachable during that time and express how you’re looking forward to connecting with them afterward.


Update Your Platforms

Next, make sure information regarding your break is on all platforms so that you’re not missing potential clients. You can pin posts to your social media, update your Google Business listing, and add a pop-up or a banner to your website. Be sure to include information about your break in your out-of-office message (and don’t forget to set that out-of-office message!). If you’re using an e-commerce system, add a message about the time off and how it will affect shipping times.

Also, make sure that you’ve marked the time off in whichever calendar or scheduler you use. Set your schedule to “busy” or “away” to make sure no new meetings can be scheduled.

We use HoneyBook as our CRM, and it’s really easy to set up the scheduler in a way that allows clients and potential clients to choose meeting times that work best for them and that also work well within our schedule.

Be sure to also communicate about recurring meetings that will be missed during the time off, and clarify the next time that you will be back in those meetings.


Respect Those You Work With

We hope this goes without saying, but be as respectful as possible when communicating about your break. You can explain how the benefits of taking that time off can have a positive direct impact on the work that you’re doing for those clients.

But, if you want your clients to respect your time off, you also need to be direct. If you’re really taking a break, don’t hem and haw about how you’ll be checking your computer sometimes.

We know it’s so tempting to do that, especially as small business owners, but it’s an important boundary to set. If it’s an emergency, of course, you would make yourself available, but you may not want to communicate that directly because it’s entirely possible that you have different definitions of the word “emergency.”

For example, as a marketing agency for small businesses, we tell our clients that holiday sales need to be planned far enough ahead of time for strategic execution—not last-minute fire sales dreamed up the night before. Clearly communicating this with our clients helps them prepare for their end-of-year sales and gives us the capacity to strategically market these special offers.


Reasons to Consider Extended or Regular Breaks

From an external viewpoint, taking extended time off can be scary because you don’t want clients to think that you’re abandoning them or are taking a vacation on their dime. But that’s not at all what’s happening.

Frame your break as a time to spend with family and loved ones. That’s something that all human beings want and deserve, and that time should be respected. If your clients can’t respect this, then you might need to ask yourself if those clients are truly your ideal customers.


Saving Money in the Long Run

Internally, your instinct might be to think about your bottom line. You might think about how the number of hours out multiplied by the number of employees is a large amount of productivity or sales lost.

But, if you reframe your perspective, you realize that by taking time off, employees are more productive, healthier, and more satisfied when they return to work. This can lead to higher retention rates and lower insurance costs—potentially saving your company thousands of dollars.

In addition, for small businesses or nonprofits, time off is an amazing benefit that you can provide for your staff—especially when big bonuses, salary bumps, or benefits like health insurance or 401(k)s are out of the picture.

Basically, scheduling breaks for your team is a great way to serve them, and when your team feels valued and well rested, your business—as a whole—will be able to better serve your customers.


Options for Those Who Can’t Afford Extended Breaks

If you have a business that depends on walk-in customers, does most of its business around the holidays, or really can’t let the whole staff off at the same time, you still have options.

For example, consider staggering the time off dates or the number of staff or departments who are off. Or schedule time off immediately after the big holiday push. This is a great way to thank your team for all of their hard work over the course of the holiday season.

Whatever you decide, just make sure that all levels of employees get some amount of time off and that these benefits are clearly communicated.


If your small business has never taken an extended break, scheduling time off might seem like an impossible feat. However, it comes with many benefits. As someone who has been overseeing this process for the Treefrog team for years, Mary wants to assure you that time off comes with big benefits and that once you have a system in place that allows you to plan for the holiday season, this process becomes less and less intimidating and more and more rewarding every year.


Links & Resources Mentioned in This Episode




The Priority Pursuit Podcast is a podcast dedicated to helping small business owners define, maintain, and pursue both their personal and business priorities so they can build lives and businesses they love.

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We are joined by Mary Adkins as we discuss how to prepare your small business to take time off during the holidays.



Leverage Kelly’s marketing experience, insights, and leadership to grow your business.

As the founder and chief marketing strategist at Treefrog Marketing, a co-host of the Priority Pursuit Podcast, a StoryBrand Certified Guide, and fractional chief marketing officer, Kelly Rice has spent more than two decades helping small businesses take their companies to the next level by providing trustworthy leadership and building effective marketing strategies and systems.

She has dedicated her career to helping small businesses succeed because she knows, firsthand, how hard they work to make their communities a better place. 

Still, many people undervalue the strength and ingenuity of small businesses, but not Kelly. She believes they deserve to have a marketing partner and strategy that works as hard as they do.

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