6 Best Local Side Hustles To Earn Extra Cash This Winter

Truth be told: winter sometimes feels like a burden. Now, I know, this season is supposed to be the most wonderful time of the year with the holidays and lights and gifts, but if we’re being honest, it’s just so dang expensive.

Heating the home during the frigid months of January and February is enough to push some near bankruptcy. Throw in those Christmas or Hannukah gifts, and the costs just keep rising.

Fortunately, there’s a way to keep yourself afloat even during the coldest months of the year. I’m talking about local side hustles.

Local side hustles are usually the best side hustles. While using third-party, corporate apps can put a little extra cash in your pocket, at the end of the day, those corporations take too much of the overall cut and are the ones really making bank.

But focusing on your community with local side hustles will keep your money in your pocket. I mean if you work for your money, you want to keep your money, right?

Now, finding local side hustles may seem difficult at first, but that’s why we’ve put together this short guide to the 6 best local side hustles to earn extra cash this winter and make this season truly special for everyone you love.

Local Peer-to-Peer Delivery Services

Amidst the Great Resignation of 2021 and 2022, formerly employed workers began finding new ways to make money, and many turned to app-based delivery services. However, many of these services have consistently run into problems: low pay for drivers, unfair work expectations, and awful driver and customer support to name a few.

Fortunately, Joey is a peer-to-peer delivery service that connects drivers with individuals and businesses to deliver their goods within their community.

Finally, a delivery service that made going to the post office redundant, saving you from driving half an hour just to get something delivered.

Better yet, if you’re looking for a good side hustle to earn extra winter cash, Joey often pays drivers more than most other corporatized delivery services like Uber or Doordash. And they do so without all the stress and hassle you face dealing with those cumbersome Big Tech companies.

Even better, They’ll even reimburse you for any necessary tools you’ll need on the job, including:

  • A dolly
  • Cargo Straps
  • Moving Blankets
  • Other tools as needed

In other words, Joey treats its drivers like human beings, not robots. The people at the company actually care about the communities in which they serve. They even work with local non-profits like Last Mile Food Rescue to help fight food waste and get it to those who need it most. This is just one of the ways Joey feels a moral and social responsibility to the communities they help serve.

Specialized Handyman — Furniture and Gift Assembly

A great side hustle for people who love to fix things is becoming a handyman. While handymen are needed throughout the year, the winter months see an increasing demand for furniture and gift assembly.

During Christmas and Hanukkah, many people are gifted desks, beds, dressers, nightstands, or other furniture. While some of this is easy to put together, others require a lot more time, effort, and skill.

Handymen who specialize in furniture and gift assembly immediately differentiate themselves from competitors with a side hustle that is in high demand during the winter. What better way to fill your pockets with extra cash before the spring flowers even start blooming.

Home Winterizer — Another Handyman Specialty

If you live in the north, then you know that winters can come in quickly, harshly, and often without any forewarning. If you haven’t winterized your home, then you could suffer frozen pipes, exceedingly expensive electric bills, and much worse.

Thus, handymen who specialize as home winterizers can make a lot of extra money by doing little things to make your home stay warmer in the winter.

Some common things you might do while side hustling as a home winterizer include:

  • Installing heat tape on incoming and outgoing water lines
  • Caulking gaps along the walls or windows
  • Replacing screen doors with those designed to better withstand winter conditions
  • Icing the walkways around the house
  • Spraying windows with ice defroster
  • Placing tarps over garden beds
  • Testing and installing a spare generator
  • Turning on the pilot light in a gas furnace

Of course, there are many other things involved with winterization, but these are just a few services you can offer to make a little extra Christmas cash before the first major winter storm strikes.

Snow Removal — A Recurring Winter Side Hustle

While salting walkways helps to reduce ice buildup, ice alone can’t prevent the driveway or sidewalk from piling up with snow during those winter storms. Instead, this snow will have to be removed by hand or machine.

Unsurprisingly, most people don’t look forward to shoveling snow away from their car just to get to work on an icy winter morning. They’d rather just pay someone to do it for them.

If you’re side hustling as a home winterizer, you can promote snow removal as a part of your winterization process. This means that you can continue building a relationship with the homeowner while making money with them all winter long.

Furthermore, if you have a truck or large vehicle, you can take your snow removal game to the next level by installing a snowplow on the front of your vehicle. While this will require you to invest in your side hustle, it’s an investment that pays off.

With a snowplow, you can clear ten driveways in the time it’d take you to clear one with just a snow shovel. Plus you can do it from inside your heated truck.

Even better, you can talk to small businesses, apartment complexes, churches, and other buildings with large parking lots. Chances are they need the services of a side hustler with a nice snowplow.

Pet Sitting and House Sitting — 2 Side Hustles That Work Together

While pet sitting and house sitting technically count as two distinct side hustles, we’ve included them together because you can often do both at the same time.

During the frigid winter months, lots of people travel to visit family or simply get away from the bitter cold for a week or two. While they’re away from their home, they’ll often want a housesitter to stay in the home or at least check in on it every so often.

Additionally, many homeowners have cats, dogs, birds, or other pets that will need to be taken care of during their absence. They will need to be fed, let outside, played with, and just generally be loved and cared for.

Thus, house sitting and pet sitting often go hand-in-hand while requiring very little hard work. Basically, you get paid to play with cute animals and make sure no one breaks into the house.

One benefit of doing both side hustles is that you can invoice the client for two gigs or combine the amount you’d charge for each into one larger sum, meaning more money in your pocket.

That sounds like a pretty sweet side hustle to us.

Choosing the Right Side Hustle

Now that we’ve made it this far, you probably want to know how to pick the side hustle that’s best for you. Well, there are a few things to consider:

Do you have the tools needed for the job? For example, if you want to be a driver for Joey, you’ll need a car or preferably a truck. If you want to assemble furniture, you’ll need a few basic hand tools.

Is there an initial investment? If you don’t have the proper tools, you’ll need to buy them. Hand tools or a snow shovel may be inexpensive enough to afford, but a snow plow for your truck may be outside your budget. You’ll need to consider these costs before just jumping into a new side hustle.

Can I reimburse my initial investment? While the side hustles on this list can be very lucrative, the only way to reimburse your initial investment for most of them is to do the gig and make back whatever money you spent to get started. However, with Joey, you will be reimbursed for any supplies you have to purchase to complete the job including blankets, cargo straps, dollies, and more.

How much money can I reasonably make? First, you want to research how much you can reasonably make doing a specific side hustle. You can look around online or even talk to people you know who are already doing the side hustle you’re considering. Just remember to take all of your costs and initial investments into consideration from the start. If you don’t, you may end up making a lot less money than you initially predicted.

By asking these questions, talking to others, and testing the side hustles for yourself, you’ll begin learning which ones can make you the most extra cash this winter and which ones are just a drain on your time and wallet.

— By Alexander Fred