5 Winter Side Hustles That Will Pay Upwards of $8,000 a Month

5 Winter Side Hustles That Will Pay Upwards of $8,000 a Month

Every winter offers opportunities for ambitious side hustlers to bring in a few extra bucks.

Standard cold-weather money-making gigs include things like working for tips at Christmas tree stands, wrapping presents in retail stores and selling homemade crafts or sweaters. But if you live in the right region and have the right skills, you can earn more in one season than some people make all year.

Here’s a look at five winter side hustles that could put you in the six-figure range if they ran all year long. Four are highly specialized, but one is open to just about anyone.

Wilderness Guide

If you’re a skilled and experienced nature enthusiast who likes educating and leading people, you can put your talents to work for real money this winter in the great outdoors.

“Wilderness guides plan and accompany small groups on adventures like snowmobiling expeditions to remote vistas, ice-fishing jaunts to frozen lakes and dog sled rides through snowy forests,” said Ricky Torres, an SHRM-certified human resources professional, strategic manager, mentor and lead contributor for SMB Guide. “Guests can pay $150-$300 per half or full-day experience.”

Right now, Indeed has a seasonal job listing from Yellowstone Adventure Tours for a Naturalist Guide that pays $275 to $600 per day plus a whole bunch of perks.

In the middle of that range at around $450, you’d have to work 17 or 18 days to pull in $8,000 a month — but the money doesn’t come easy.

“The work is exhilarating but also carries responsibility for safety,” said Torres. “Strong stamina, navigation skills and a calm, empathetic manner are musts for this job.”

Holiday Home Interior Designer

Some people look forward to decorating their homes all year long as part of their annual holiday family tradition. But others care more about the results than the process — and they’re willing to pay big bucks for a look that’s more Hallmark Channel than DIY.

“As the holiday season ramps up in late November through December, many families and businesses require extra help decorating their homes, yards, stores or venues for festive events,” said Torres. “Having started a seasonal decoration installation business in college, I can attest to the demand.”

According to Angi, the price ranges from $300 to $2,500 with the average job paying $1,500. If you earn around the average, you’ll be able to clear $8,000 with five or so jobs per month.

Exterior Light Hanging and Removal

It’s not only the inside of houses that earn creative side hustlers serious money in the winter. The outside can bring in just as much income or more. 

“The tradition of hanging Christmas lights every year gets people excited and in the mood for the holidays,” said Tyler Schnelli, founder of CampingTactics.

“A side hustle that has worked well for me in the past was hanging lights for individuals as well as businesses. You offer the job at a price based on the size of the house and the scope of the project with the promise to come and remove them at the end of the season.”

According to Angi, the average job for a small, one-story house pays $400 — or $1.25 to $3 per linear foot — for labor alone. If you’re willing to invest in lights, you can charge $2.50 to $7 per linear foot.

Forbes says work on two-story homes that involve ladders pay an average of $400 to $1,200 and three-story homes pay $700 to $1,800.

Even the average one-story home without lights would require you to do only 20 jobs to pull in $8,000 per month — and remember, you can double-dip by charging to hang them up and charging to take them down.

Ski/Snowboard Instructor

Ski resorts charge a pretty penny for skiers and snowboarders to ride their slopes — and they charge an even prettier one to teach newbies the ropes. If you’re skilled and experienced enough to teach the technical and safety aspects of the sport, you can clean up every winter by doing what you love.

Currently, Indeed is listing ski and snowboard instructor positions for $50 an hour at Smugglers’ Notch Resort in Vermont. Wildcat Mountain in New Hampshire pays up to $62.52 an hour. At Mammoth Lakes in California, it’s more like $80 an hour.

In the middle at around $62, you could land your monthly $8,000 with around 30 hours of instruction per week.

Professional Snow Removal

The previously mentioned side hustles pay big money, but they all require specialized skills, experience and in some cases, certifications and equipment. But the one winter gig that just about any able-bodied person can do is a longtime classic in regions where heavy, frequent snowfall is part of life in the cold months.

“A couple of years ago, my son undertook snow removal services in our neighborhood, which turned out to be a profitable venture in areas blanketed with snow during winter,” said Roksolana Ponomarenko, Chartered Financial Analyst (CFA) and business advisor at prm.com.

“My son found that for about two to three hours of work each morning, he could earn between $50 and $100. Remarkably, he would complete his tasks by 10 a.m., leaving the rest of the day free. This side hustle not only offers a significant earning potential but also allows for a flexible schedule, making it an ideal winter job.”

But shoveling the neighbors’ driveways and sidewalks for spending money is nowhere near this gig’s upper limit. 

For example, a landscaping company in Cincinnati, Ohio, called GroundSystems is currently hiring people for snow removal service. They have to agree to a 24-hour on-call schedule and report on-site within one hour of a call when it snows, but they pay $50 to $90 an hour. In the middle at $70, you could reach $8,000 per month by working around 28.5 hours per week.

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