11 ways to enjoy the holidays while running your business

The holidays are a busy, exciting, stressful time to run a small business. When you’re managing everything on top of gift shopping, party hopping, and family outings, your schedule can feel a bit overwhelming. Thankfully, here are simple ways to enjoy your holidays while you run your business from afar.


Get ahead

Your extra efforts in October really pay off in December, just as your hustle in January clears the path for a calm spring break. So aim to get your biggest projects done well in advance to ensure you have free time between Christmas and the New Year. You’ll be far less stressed come Christmas Eve, so you can actually enjoy your time off without worrying about deadlines.

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Schedule time off first

Want a healthy work-life balance over the holidays? Book off your holiday time before you plan the rest of December. Want a little scheduling help? Get your phone out—there are hundreds of time management apps and these 15 apps are among the best.

“Schedule time off in advance. It’s important to schedule it in your calendar before anything else, otherwise, time gets filled up and all you do is end up working anyways.”

– Diane Conklin, President of Complete Marketing Systems

Pick a time when business is slow

Sure, you’ll often miss out on business when you take time off, but you can minimize the impact by choosing a quiet period to take your vacation. Look at your slowest business weeks in the last five years and pick that week as your time to fly away. Depending on your field, take a week off when your clients are off, too, as this can maximize your family fun while reducing your vacation stress.

Let your leaders lead

Are you keeping the business open while you’re gone? Then it’s time to delegate. You’ve built an amazing team that understands all aspects of your business, so trust them to handle any situation, whether or not you’re physically present in the office. Relax, breathe, divide, and conquer, because your team has got you covered. Need a little hand delegating? These delegating apps make assigning tasks about as easy as boarding your plane to Phoenix.

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Over prepare

As the saying goes, “Trust but verify.” Though you trust your employees to do a great job while you’re away, it pays to over-prepare them for every eventuality. A month before your vacation, sit down with your team and go over as many potential situations that could come up while you’re away and how to handle them. Take detailed notes and turn it into a document you share with everyone. It should cover who is taking on what tasks while you’re away and who to contact in case of emergency. A week before your trip, go over this document again. It might seem like overkill but everyone’s comfort level will be a lot higher.

Protect the getaway

Don’t schedule anything to go "live" (e.g., a new website or ad campaign) right before your holiday or while you're away. You don’t want to be dealing with last minute problems or errors as you're getting on the plane, or when your family is waiting for you on the beach.

Prepare your clients

You’ve prepared your staff, now it’s time to prep your biggest clients. Alert them in advance that you’ll be unavailable during your vacation. Assure them that you’ll tackle any of their concerns well in advance of your trip. And if your clients might be procrastinators who could bombard you with last-minute requests, tell them your vacation starts 3 days before you actually go. Same goes for the tail end...tell clients you'll be back at work 2-3 days after you actually return. This gives you time to get up to speed before you have to deal with client issues and concerns.

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Shut it down

Some small businesses choose to close up shop entirely when they go on vacation. You can keep your website running but add a notice on your landing page that specifies the dates you’re closed and encourage visitors to browse while they await your return. Give advance notice of your vacation on all your social media channels—you might discover that it works as a limited time offer to boost sales before you go. Many of your return customers will be encouraged to hear you’re taking time off for a rest. It may even increase their affinity for your brand, instead of cutting into your sales. Here are more tips on ‘going dark’.

Set holiday rules for yourself

Avoid the trap of letting yourself get sucked into working on your small business on every day that you’re away. Set a time of day (and a time limit) for when you’ll check in on your business during your vacation. Pick a time of day when you’re likely to be hanging around the hotel anyway. This can be 30 minutes early in the morning and maybe 45 minutes every evening when you return from dinner.

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Embrace the analog

Take a tip from Richard Branson, and leave your phone alone for an afternoon and use a notebook instead. You never know when that next great idea will hit you like a warm wave to the face. Test out the Hatch notebook, which is designed especially for entrepreneurs to boost productivity. It’s got designated spaces for outlining your small business ideas, challenges, features, markets, and demands.

"I make sure that I disconnect by leaving my smartphone at home or in the hotel room for as long as possible—days, if I can—and bringing a notepad and pen with me instead. Freed from the daily stresses of my working life, I find that I am more likely to have new insights into old problems and other flashes of inspiration."

– Richard Branson, Founder of the Virgin Group

Want more sage advice on how to relax when you’re the boss? Here’s how Branson and other CEOs take time off each year.

Decrease your options

There’s more to life than growing more and more business streams, every single day of the year. Nobody knows that better than the co-founder of the j.k. Living Foundation, Matthew McConaughey. Listen to his inspiring speech on the true definition of personal success.

McConaughey’s biggest tip for small business owners like yourself:

“Too many options will make a tyrant of us all. So get rid of the excess. The wasted time. Decrease your options. And if you do this, you will have accidentally, almost innocently, put in front of you what is important to you.”


Then hit the beach, grab a second helping, meet up with friends (or your own family!) who you haven’t seen in weeks or months, and settle in for a wonderful holiday season.

Any tips we’ve missed on how to enjoy the holidays while keeping your business humming? Share it with us on Facebook and have a great holiday with your loved ones.

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