By Bryan Robinson,Contributor,Ph.D
Copyright forbes
The National Retail Federation reveals that the 2024 November-December holiday season (Thanksgiving, Christmas, Hanukkah and Kwanzaa) totaled $994.1 billion, which demonstrates the sustained, year-over-year opportunity for Holiday season side hustles.
Holiday season side hustles have become huge money-making ventures, collectively yielding millions, as the the season starts earlier and lasts longer. It has evolved from isolated celebrations into a continuous October-through-December spending phenomenon, creating unprecedented opportunities for side hustlers serving multiple occasions. The extended holiday season presents one of the most lucrative windows of the year for side hustlers and aspiring entrepreneurs starting holiday season side hustles, raking in millions of dollars.
Holiday Season Side Hustles Are Becoming A Hot Market
Side hustlers are discovering that holiday seasons have become big business for them. A notable 71% of the workforce is searching for side hustles or second jobs with another employer. Over 36% of Americans have a side gig, with Gen Z showing the strongest engagement at 48%, while millennials follow closely at 44%. Gen X accounts for 33% participation, and baby boomers represent 23% of side gig workers.
If you’re looking for high-earning side gigs, the search has gotten easier, but side hustlers are raising the standards for success, treating them like serious startups, using AI–the very technology replacing them–to meet customer expectations.
Case in point. In a recent story for Forbes.com, I wrote about how the Halloween and fall season have evolved from a single-night celebration into a month-long spending phenomenon, creating unprecedented opportunities for Halloween side hustles.
From August through November consumer demand has created a spike for autumn-themed products and services as weather affects spending patterns, and the gift-giving cycle accelerates from Halloween through December holidays, creating opportunities for side hustles.
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But that’s not all. According to the National Retail Federation, the holiday season represents massive consumer spending from the spooky night through the December holidays and up to the New Year. They predict that spending for Halloween 2025 will reach a record $13.1 billion, while the 2024 November-December holiday season (encompassing Thanksgiving, Christmas, Hanukkah, and Kwanzaa) totaled $994.1 billion, which demonstrates the sustained, year-over-year opportunity for entrepreneurs and side hustlers.
5 Holiday Season Side Hustles You Can Start Today
Jeff Corbo, president of the online printing service DocuCopies.com, says the holiday cascade creates ideal conditions for side hustlers. He explains how entrepreneurs who launch in October establish customer relationships that carry through three distinct revenue opportunities.
“A family that trusts you for Halloween decorations becomes your Thanksgiving client, then your Christmas customer,” Corbo declares. “You’re not starting from scratch three times; you’re deepening existing relationships.” He shared with me five holiday season side hustles that you can start this weekend.
1. Custom Holiday Prop Signage
He mentions that decorators invest heavily in creating memorable displays for every holiday but struggle to find unique signage that matches their vision, adding that you can reuse them for each holiday season side hustle. “Custom cemetery signs transition into ‘Thankful for…’ yard displays, then become ‘North Pole This Way’ Christmas directionals,” adding that, “Serious decorators build Instagram followings around their seasonal displays and consistently credit their sign creators, generating organic referrals throughout decorator communities.”
2. Seasonal Baked Goods And Dessert Boxes
“Families increasingly seek convenient, homemade-quality treats for each holiday milestone without the time investment of baking themselves,” Corbo points out. “Halloween sugar cookies become Thanksgiving pie deliveries, then transform into Christmas cookie gift boxes. Home bakers with cottage food licenses can start with their existing equipment and scale based on demand. The same customers who order Halloween treats for classroom parties return for Thanksgiving hostess gifts and December cookie platters for neighbors and coworkers.”
3. Holiday Event Planning And Coordination Services
Corbo suggests that PTAs, churches, corporate offices and neighborhood associations host multiple events from October through December but lack bandwidth to manage logistics.
“Event coordinators who handle one trick-or-treat naturally become the first call for Thanksgiving potlucks and Christmas parties,” he contends. “Each successful event generates referrals to other organizations planning similar gatherings. This service requires no upfront inventory, but just organizational skills and relationship-building.”
4. Custom Gift Labels, Tags And Stationery
Another example Corbo offers for the sustainability across holiday seasons is the “You’ve Been Booed” tradition in October, which introduces families to personalized gifting materials that translate into “Thankful Tags” for November and elaborate Christmas gift presentations in December.
“Customers who purchase custom labels for one holiday typically order for all three, often increasing their budget with each order as they see how personalized touches elevate their gift-giving,” he states, “The same templates adapt across seasons with color and graphic adjustments, maximizing design investment.”
5. Seasonal Home Styling And Decorating Services
Corbo notes that busy professionals and elderly homeowners want festive homes for each holiday but lack time or physical ability to decorate themselves. He declares that if you’re a decorator who installs Halloween displays, you earn trusted access to clients’ homes, becoming the obvious choice for Thanksgiving mantels and Christmas tree setup. “Premium clients often book all three holidays upfront, providing guaranteed income through year-end. This service leverages existing decorations many people already own but don’t have time to display properly.”
A Final Takeaway On Holiday Season Side Hustles
“The most successful holiday entrepreneurs recognize that they’re contributing to memory-making during the most emotionally charged months of the year,” says Corbo. “Families remember who made their celebrations special, who delivered when they promised, who understood their vision.”
I spoke with Alex Avramenko, head of commerce growth at Godaddy, who told me that as Gen Zers raise the bar, it’s a wake-up call for anyone selling through side hustles. “If your online store isn’t optimized for how people actually shop, even your best product won’t save you,” Avramenko cautions. “Your customers have already moved on.” He emphasizes that meeting modern customer expectations is the hurdle, not just launching a side hustle.
And Corbo seems to have the ticket, suggesting that you start in October, deliver exceptional experiences and your Halloween customers will become your foundation for a profitable quarter of holiday season side hustles. “The entrepreneurs earning five figures between now and January 1st are doing something consistently well across multiple holidays,” he concludes, “building genuine relationships one celebration at a time.”
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