Entrepreneur’s Nightmare Before Christmas: Balancing Work and Play During the Holiday Season

While everyone is taking a well-earned break, you know that you can’t really stop working. After all, there are clients to please and bills to pay.

So, what’s a busy entrepreneur to do?

The holiday season is a notoriously difficult time to get work done. With most people taking a week or two for rest and relaxation, now’s not usually a good time to fund-raise, hire employees, or do much of anything that requires input from other parties.

The holiday season is a notoriously difficult time to get work done. #MichaelsWilder #entrepreneur Click To Tweet

On the one hand, you could take this opportunity to recharge (goodness knows you’ve earned it). However, you might be kicking yourself in two weeks when work comes crashing down on you and you’ve done nothing to get ahead.

That’s why this time of year requires entrepreneurs to be even more aware than usual of how they spend their time to make the most of the holiday season—both personally and professionally.

Make Your List, and Check It Twice

Take stock of your priorities.

What are the things that you absolutely, positively must accomplish in the coming weeks? What are the things you want to do? What can you afford to let slip for just a few days?

It’s unavoidable that there will be things you need to do in order to keep your business afloat during the holidays, like sending invoices, completing outstanding projects, and paying bills. These business necessities, however, will be competing with the seasonal activities that come with the holidays.

It’s up to you to figure out what really matters during this time.

If spending extra time with your family or taking time to give back to your community give you a feeling of fulfillment, you need to actively carve out time for those priorities. Everything else (including your everyday time-wasters like watching Netflix or checking social media and lower priority work projects) can be wait until everything else is done.

Take Advantage of Silent Nights

During the holiday season, many entrepreneurs and freelancers take advantage of their flexible schedules by shifting their work hours either earlier or later in the day.

Getting the bulk of your work done early in the morning or later in the evening allows you to spend more of your daylight hours on all the holiday celebrations and obligations. Between gift shopping, cooking elaborate feasts, cleaning and decorating the house, and somehow carving out time to actually enjoy the holidays, you’ll want to set aside some hours during the day to prepare. However, evenings after everyone’s fallen into a Christmas cookie-induced coma or early morning before the rest of the world is fully awake are good times to get caught up on necessary work.

But don’t worry, it won’t last forever. You may pull a few late nights in the weeks leading up to the holidays, but work usually slows down by the time December 25th rolls around.

Don’t Be a Grinch

Set aside time that is strictly devoted to what matters most—whether that’s making gingerbread houses with the kids or volunteering at your local food bank.

Make sure to establish expectations ahead of time. Let your clients know when you will and won’t be available during the holidays. If you have employees or business partners, you could even create a rotating schedule to determine who’s “on-call” to allow for everyone to take a few days to spend time away from work commitments.

And, when you say you won’t be available at a certain time, stick to that. If you’re at a holiday party with your partner, don’t feel compelled to drop everything if a client calls. Let it go to voicemail.

Set a clear distinction between work hours and personal hours during the holidays to avoid the sneaky “work creep.” Work can wait. Take some time to focus on the other important things in your life.

Make Your New Year’s Resolutions

The week between Christmas and New Year’s is prime time to do a little strategic planning for your business. Usually, work is still a bit slow in the days after Christmas, and you may even have a little extra time to focus on yourself and your business goals. Use this time to plan content, work out the finer details of upcoming plans, and build out agendas for planning meetings you want to conduct after the holidays.

Now is also a good time to express thanks to the people in both your personal and professional lives. Send out a few words of gratitude to the clients, vendors, friends, and family that make your work possible.

It’s a Wonderful Life

Appreciate this time, and don’t feel guilty for taking a moment for yourself and the other people who matter in your life. The holiday season is all about recognizing the positives in your life. Take this opportunity to sit back and enjoy the fruits of your hard work. 

So, go ahead—eat, drink, and be merry! After all, you’ve earned it.

Mike Speer Administrator
Chief Marketing Officer Michaels WIlder

Opinions are my own and not the views of my employer.

Chief Marketing Officer at Michaels Wilder and an entrepreneur since before the average person knew what that even meant, Mike has helped countless businesses build effective sales and marketing strategies. His philosophy is, “If you’re not thinking 10 years ahead, you’re already behind.” Mike’s content has appeared in Forbes Magazine, Inc. and Apple News. He has also been featured numerous times as a “Top 10 Writer” worldwide on the Q&A content site, Quora.

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Mike Speer Administrator
Chief Marketing Officer Michaels WIlder

Opinions are my own and not the views of my employer.

Chief Marketing Officer at Michaels Wilder and an entrepreneur since before the average person knew what that even meant, Mike has helped countless businesses build effective sales and marketing strategies. His philosophy is, “If you’re not thinking 10 years ahead, you’re already behind.” Mike’s content has appeared in Forbes Magazine, Inc. and Apple News. He has also been featured numerous times as a “Top 10 Writer” worldwide on the Q&A content site, Quora.

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