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7 Best Holiday Side Hustles

Holiday spending is expected to top $1.2 trillion this year – Here are 7 ways freelancers can get a piece of the pie.

Happy, Merry, Holiday Economy!

In 1934, at the urging of FDR, Sears and Roebucks presented Americans with the first-ever Sears’ Wishbook. A glossy, dictionary-thick catalog of games, toys, tinned popcorn, record players, Stirling silver teapots, hunting rifles, and more; all priced to motivate what Roosevelt would come to call the nation’s “Christmas Economics.”

Ever since this hallmark moment in American holiday giving, we have seen retail, services, decor, and of course food service- all grow a two-month bump in sales. In recent years, the US Census Bureau reported month-over-month growths of as much as 54% and, in some cases, an 11.9 billion-dollar market expansion in Holiday retailing.

So the question every freelance professional should be asking is: when the pie is this big, how can I get a slice? Here are some of the best holiday side-hustles up for grabs right now!

Sleigh Bells Ring

If you (or your friends) have the gift of song, there are few more lucrative times to begin selling that talent than right now. Shopkeepers, grocers, cafe managers, clergy, and talent bookers for festivals, bars, and house parties are all looking to add a bit of musical magic to their roster. From madrigal choruses and string quartets to guitarists, jazz bands, and DJs, there has never been a better time of year to begin sharing your talent for a bit of cash.

Check forums on Craigslist and Backstage.com or booking sites like ReverbNation and SonicBids to find eager bookings, or drop into your favorite bar or shop with a demo and watch the holiday cash start to flow!

Design Some Magic

Undoubtedly, even some of the most outdated holiday traditions still endure, and postal greetings have rarely been more popular. Pandemic-era holidays at home saw the USPS reporting record delivery numbers and a return to the time when doorways, mantles, and refrigerator doors filled up with notes from friends and family abroad. Suppose you have a touch of artistic skill; calligraphers are swimming in orders for custom envelope addressing, and letterpress designers with charming printed cards will find themselves with requests for custom stationery, gift tags, and clever cards.

If you’re a more digitally talented web designer or video producer, there is a place for you in this space too! Young, creative couples increasingly convert their classic family holiday card ideas into custom Instagram greetings and email invites. If you have a knack for freelance film or contract digital illustration, leverage your skills by offering consumer and corporate clients a clean, cool, personalized digital card.

A portfolio on Etsy will be your best friend here, but consider connecting with florists, small businesses, and local event planners to find new opportunities and make a few new local business partners.

Become an Elf or Santa’s Sleigh

Between shopping and parties, decorating and planning family meals, making travel plans, and watching a gym full of kids sing Frosty the Snowman, the one thing most people run short of each winter is time.

So, if you can use your talent to sell a few hours back to the season’s weariest, you’ll find your Lili account looking cheery and bright. If you can’t get enough gold paper and glitter bows, then a custom gift-wrapping hustle may keep your hands busy and your holiday flush. Do it from the comfort of your own home, or partner with a local retailer and set up a table near the checkout counter. And for you ride-share drivers out there, don’t forget to offer local package delivery for a small but competitive fee. With the USPS more taxed than ever, providing swift delivery services will fill your pockets all winter long.

Fill bellies with bowls of jelly

Should you be a freelance maker with culinary prowess and an abundance of counter space, then making to-order pre-packaged baked goods or candy for stocking stuffers and guest gifts is a great way to turn your home kitchen into a place for rustling up both kinds of dough. Finding a niche market is a great way to separate your product from what is available in stores.

Facebook Marketplace, Etsy, and partnerships with area festivals and farmers markets have proved an essential selling tool for these crafty cooks. Consider adding bespoke packaging or custom bag tags at a special holiday rate if you’re artistically inclined.

The oldest Christmas gig in the world

Without question, the top holiday side hustle is also the oldest. In November of 1861, on the corner of 14th Street and 6th Avenue, just steps from a registration office for young enlists to the Union Army, Macy’s department store debuted a meet-and-greet with the big man himself. Santa, clad in black patent military-style riding boots and a bright red suit, brought hot cocoa to the boys in uniform and gave New York’s children a wave and a wink. For more than 160 years, the holiday season has employed thousands of Claus impersonators around the country and across the globe. If you have a gift for gab and a love for the excitement in a child’s gap-toothed smile, then you might consider playing a beloved holiday character.

Not quite old enough for the Santa gig? No worries! These days, dead-ringers for Mrs. Claus, as well as bespectacled Ralphie lookalikes in pink-bunny-pajamas and comedically gifted overgrown elves with a love of syrup, all find their way into shopping malls, outdoor festivals, theme parks, primary schools, and movie theaters.

Competition can be fierce, but your performance will be worth it if you look and act the part: PayScale reports most mall Santas clear 5-15K every holiday season, and Disney World Orlando is starting most cast members at $18-20 dollars an hour. And don’t forget to write all the dry cleaning bills and shoe shines for that iconic red suit off your taxes!

Written by

As a freelance communicator, and copywriter Steven has spent more than a decade applying futuristic thinking, visual integrity, and brand strategy to projects from behind the keyboard and in front of the camera, and he is an engaged member of the Lili-user community!