Small Business Holiday Planning: What You Need to Do NOW so You Can Actually Take Time Off

I know it’s October, but…the holidays are going to be here before you know it. The time to prep is right now. 

Because the honest truth? You won’t be able to unplug, recharge, and do all of your favorite holiday activities if you don’t plan for it now. 

Running a business is a lot of work, and unfortunately, part of running that business is having to think WAY ahead to enjoy time off. You aren’t just an employee — you’re the one making the show run! So if you don’t prepare, no one else is going to do it for you. 

Do you want to be sipping eggnog while you’re cozying up by the fireplace? Or would you rather deal with an inbox full of urgent emails, last-minute tasks, and unnecessary stress the day before Christmas Eve? 

Thought so! Let’s break down exactly what you need for small business holiday planning so you can actually enjoy your time off!

Holiday Planning Tip #1: Treat Your OOO Time Like a Doctor’s Appointment

If you don’t schedule it, it’s going to be hard to respect it. 

Think about it — when you put a doctor’s appointment on your calendar well in advance, you’re prepared for it. 

You know that on the 15th of October, you’ll need to go in for a checkup and will be offline for a few hours. When it gets closer, you plan around that time and make sure your schedule and tasks line up.

It needs to work the same way with your holiday out-of-office too. 

Decide exactly when you’ll be taking time off — don’t just assume you might take a day off here and there. Be firm and set some boundaries! Get specific. Pick the exact dates you want off, when you want to log back on in the new year, and block them off on your calendar.

You might be tempted to leave your calendar open “just in case” something comes up, but resist that urge! The clearer your boundaries, the better you can recharge. Trust me, your clients and business will survive without you for a few days 😉

Holiday Planning Tip #2: Give Your Team Enough Time to Prepare

Once your OOO dates are locked in, loop your team in as early as possible. The sooner they know, the sooner they can get prepared. 

Let them know when you’ll be out and what they can expect while you’re away. 

(Pssst…this is the PERFECT time to create SOPs!)

Once they know when you’ll be out and what they can expect, give them time to ask questions or request anything they’ll need. Bonus points for creating a task to do this so no one forgets and asks the day before you’re out!

Overlap in OOO?

Keep in mind that providing your team with this type of communication isn’t just the polite or kind thing to do — it’s absolutely essential for keeping things running smoothly. By giving them enough lead time, you’re empowering them to handle any potential issues without you. 

This will be especially helpful if there’s any overlap in the time you and your team take off. While I surely hope that you’ll set them free during the holidays, I know many small businesses run on a team of contractors who set their own schedules. 

There will undoubtedly be some overlap. So make sure you’re prepared to help others keep doing their job while you’re not online at the same time!

Holiday Planning Tip #3: Communicate with Clients and Community

Now that you’ve talked to your team, you need to let your clients, customers, or community know you’ll be out. 

If you work with 1:1 clients, send them a personalized heads-up about when you’ll be unavailable and provide any last-minute support they might need before you go offline.

For those running courses, memberships, or managing an online community, be sure to send out an announcement letting them know responses will be slower than usual during the holidays. 

Feeling Guilty?

Here’s the thing to remember: You are NOT under serving your clients or community by taking time for rest. 

The holiday season is a natural downtime, and no one will fault you for setting boundaries and stepping back to recharge. In fact, they’ll probably respect it since they’re doing the same!

Holiday Planning Tip #4: Review Your Task List and Create a Game Plan

Before you step away, do a thorough review of all your tasks, projects, and responsibilities that will need to be taken care of while you’re OOO. Then figure out…

• What’s essential? If you have tasks that absolutely need to be handled during your time off, see if you can delegate them to a team member who will be online and set up an SOP so they can manage without needing to contact you.
• What can wait? You and I both know not everything is as urgent as it feels. Most things can be pushed out and rescheduled in the new year.
• What needs to be done in advance? The point of taking time off is to rest and recharge. The last thing you want is to log back on January 2nd and feel absolutely swamped with tasks. Batch your work and knock out as many “before the holiday” tasks as you can. You’ll feel so much better knowing that future-you won’t be drowning in work when you return!

Holiday Planning Tip #5: Do Your Annual Planning 

As part of those batch tasks I mentioned above, take some time to do some business review and planning. The end of the year is the perfect opportunity to reflect on what worked, what didn’t, and how you want to shape the upcoming year.

This is the best time to get honest and see what you can continue doing well or change to do better in 2025. Then, you’ll be able to start the new year with a clean slate!

Holiday Planning Tip #6: Figure Out Your Content Calendar

Will you be posting content while you’re away? Or will you pause it too? I have clients who do both, so there’s really no wrong answer here! You just need to choose what’s best for you and your content goals.

If you plan on keeping up with your content though, you need to prep before you and your team are OOO. 

If you decide to pause content, make sure you communicate that with your audience in advance so they don’t think you just fell off the face of the earth!

Holiday Planning Tip #7: Handle the Final Admin Tasks (And Pour the Eggnog!)

Finally, you’re going to want to do one last sweep before you slam that laptop shut.

• Set your OOO email autoresponder so people know when they can expect to hear back from you.
• Reschedule any task due dates in your project management system so you don’t have deadlines looming over you while you’re away (or stressing you out when you log back on).
• Schedule a final reminder email to your team and community to let them know when you’ll be away and what they need to do if they need something. 

Once you’ve wrapped up these tasks, bring out your favorite Christmas mug and pour yourself a glass of (enhanced) eggnog. You deserve it!

Need Help Getting Ready?

Feeling like your to-do list may be too big to tackle in time for the holidays? Let me help! As an OBM, I can help you figure out what to delegate, how to create SOPs to instruct everyone on what to do while you’re away, and cheer you on as you knock out all that pre-holiday prep!

That’s not all I can help you with though. If you want an ops-partner who will help you carry success into the new year, learn more about what I can help you with here!