16 unique winter side hustle ideas you have to try!

It’s 20 degrees outside and I’m freezing my butt off. What are some side hustle ideas I can explore?

You may be like me. I’m not a winter fan. I try to figure out ways to keep occupied during winter. Here are some side hustle ideas to think about.

Sell items on Ebay or Craigslist

A lot more people are home watching their computer screen in the winter than in the summer. Try to monetize those eyeball buy selling things on these platforms.

Testing websites

Changes are you not going to be outside. You should do something profitable with all the free time you have. Testing websites will keep you mind off how cold it is outside.

Testing website by Christina @ Wocintechchat
Testing website by Christina @ Wocintechchat

Writing an e-book

Trying to write an e-book in the summer with all the sun and beaches is probably a non-starter on your part. As it gets cold, having a topic to focus on will help you get through those winter months.


It’s very hard to proof your own work. You wrote it and it’s easy to miss errors. Use this fact to your advantage. Find errors in other people’s work for them. This is a very valuable service to offer.

Selling your books

I find myself reading more books in the winter than the summer. I finish books faster because of this. I think many people are doing this too. You may be able to sell the books you read to others reading during the winter.

House sit

This can be a gold mine. Many people flock to warm location during the winter. It’s very common for people to spend a month in an exotic location in winter. When a person goes for an extended winter recess, they need someone to water the plants and make sure the pipes didn’t exploded because of the later winter storm that came into the area. You can be their sitter and deal with any problems that come up.

House sitter by Chris Lawton
House sitter by Chris Lawton

Remove snow

I cleared my parents sidewalk and driver way as a kid. I thought, wait, I think people will pay me to do this. Guess what, they did. I live in a big city. Whenever it snow, people don’t know how to deal with it. We have laws in place to make sure the side walks are clear so people can walk to where they need. Many people elect to use a service to remove the snow. It’s very easy to undercut the high price options.

Become a personal shopper

It’s cold and people want an easy button. Going out and to shop for people can be an option. I think about people that are older. Providing personal shopping services for them can be very valuable for them. Cold and rainy weather can cause a lot of older people problems. No need to go down that path, shop for them.


The school year starts in fall. By the time we get to winter, the school year is in full swing. There are tens of thousands of students studying many subjects in winter. So there’s a pretty significant market for tutoring services. Why? Because people learn differently. Some people need additional help and tutoring is a great option.

Drive others people around

Uber and Lyft for the win. The cool thing about these platforms is that they’re everywhere. More people are ditching cars and opt-in for using ride share. While driving for Uber and Lyft, you can prospect for customers. You potential customers are literally sitting in your car.

Sell last season’s clothes

Unless you go to New York Fashion Week, telling the difference between this and last season’s clothes is not a skill you’ve mastered. This is fine. Many other people are like you.

Start a blog

This is another activity to get your mind off the cold weather if you’re not a winter person. Blogging can be therapeutic and lucrative. It’s not that hard to get started. I really like how blogging can take you to any place you want to go. You could be in your house in the middle of a blizzard, but you’re writing about how much you love the mai tais in San Pedro.


Trees need attention. During the winter is when you want to do some activities with trees. Have you heard of winter dryer or winter burn? Trees can die from this. This can make them a fall hazard. A fallen tree can land anywhere. It would be bad if the tree lands on a car or house. If you become an arborist, you can help people that experience problem.

Beautiful tee by Todd Quackenbush
Beautiful tee by Todd Quackenbush

Wilderness instructor

Teaching wildness survival in the winter to me is great proof that you mean business. You out in the cold teaching. How badass is that? I think your students will listen more attentively due to it being cold. You put people in a forest. It’s cold and light snowing. No one wants to be cold. You have tips to being there and not being cold. You are providing a wonderful service to your students.

Make holiday cards

Many people still send Christmas cards every year. This is a tradition that people faithful follow. You can plug into this tradition but provide customized cards to your customers. If you’re artistic, you may want to give this serious thought.

Selling Roasted Chestnuts

I came across this one on Quora. Jonathan H. talked about how he saw this in Montreal years ago. After I read this I thought about the Nat King Cole song. Check out this this video.

Nat King Cole – Chestnuts roasting on an open fire

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