The holiday season is supposed to be about getting together with loved ones, indulging in good food and drink, and finding a some time to kick back a little and reflect on the year that's passed.

Many entrepreneurs might respond: yeah, right.

While everyone hopes to relax and rejoice as the year comes to a close, all too often business owners find this time of year to be a manic flurry of seasonal promotions, forward planning, and insane hours (or, for some, a far worse pause in getting paid as clients turn their attention elsewhere). Gingerbread and holiday parties might make up for some of that, but the sum total of the experience is often exhausting rather than refreshing.

But it can be different, insisted Kate Hamill on The Freelancers Union blog recently. All it takes is a little planning.

Prep now, chill later

As long as this isn't your first time at the entrepreneurship rodeo, you probably have a good idea what's coming. Whether you experience the holiday period as a lull or utter lunacy, the key to carving out the time and headspace you need to actually celebrate the season is to think ahead, according to Hamill.

"November is a good time to start really preparing for the end-of-year bottleneck of holidays and celebrations. What can you do now to make things run smoothly in late December?" she asks. "You can't control what your clients do, but you CAN do extra prep now to reduce chaos later. Get invoices pre-loaded and ready to send. Aim to finish up projects and meet deadlines before the holidays hit."

'Tis the season for budget chaos

Folks' finances tend to go a bit crazy over the holiday. For some business owners that can mean a seasonal cash flow headache as clients take longer to pay (or stay away entirely) and holiday expenses add up.

"Create a special budget for the end-of-year period. Too many of us try to blithely skate by on our normal budgets, and have mild cardiac incidents when receiving credit card statements in January. Make room in it for extra costs and delayed payments, if possible," instructs Hamill.

Send those holiday cards out

The holidays are also a great time to drop a note to your clients -- not just to wish them well during the festive season, but also to remind them what you've been up to, keep them in the loop about any discounts or offers you have going, or even gently nudge them to please pay you.

"Prep your Happy New Year / Happy Holidays cards to clients in November. Not only is it nice... it's a good marketing tool," Hamill reminds entrepreneurs. "Make sure to thank them for the previous year's work (mentioning specific things you've accomplished together is always smart), and make noises about more collaboration in the future. It's also a convenient, sneaky reminder about pending invoices--nothing says 'remember to pay the freelancer' like a holiday card on a desk."

Published on: Nov 25, 2015
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