8 Seasonal Side Gigs To Make Extra Money For The Holidays

Recently, I’ve been looking for fall, or winter-centric side hustles. I wrote a piece about side gigs to do on the weekend for extra money, and wanted to find additional jobs that relate specifically to the season. As someone who worked in the service industry, right away I noticed a problem in finding side hustles as the weather gets cold. The late fall and winter months are notoriously the “off season” —  there are fewer shifts at restaurants, not many opportunities at attractions like wineries and breweries, and wedding season is over, so catering jobs can be a bit sparse. Even dog walking opportunities are slimmer as the cold sets in. When I worked at a winery, and waited tables, it was a huge struggle to get through December, because the tables were slow, and shifts were constantly getting cut.

October and November might be challenging months for extra money, but they’re also the months where we need cash the most. With every year I age, I feel like holidays get more expensive. There are more people to buy for, and while it’s a good thing if your gift-giving circle expands, it’s also more stressful, and a bigger strain on your finances. (Not to mention traveling during the holidays makes the whole situation twice the price.)

So while the more obvious gigs might not be an option over the next few months, there’s still time and side hustles to give you a little cushion before the holiday expenses creep up on you. Here are eight options to consider:

1. House or pet sit.

Last Thanksgiving, my boyfriend and I stayed in LA (with most of our friends) because it was too expensive to fly anywhere. Generally, people who are traveling and have pets will pay you a fair daily rate to house sit, and will pay even more if they require you to spend the night at their house while they’re gone. We house/pet sat for a friend and made $250 for four days. If you are heading home for Thanksgiving, ask your parents if any of their friends are traveling, and maybe you can pet sit while at home, spending time with your family. (If you need an escape from all the relatives, “I have to leave by 10 to go house sit” is a reliable excuse.)

2. Work late at company events.

For a few months, I worked on the internal events team for an ad agency, which was a lot of fun. Leading up to Thanksgiving, we had several events that required I work late. However, our team was so small, that we needed a few extra hands from different, unrelated departments. A few of my entry-level colleagues offered to assist, and were paid overtime for helping out. If you’re looking for some extra hours on your time sheet, ask the team who does in-house events, or the office services team. If you work at an office with a lot of families, offer to help out and set up an option for people to bring their kids to the holiday party. I’ve seen offices have a “kids’ room” during their office parties, and you can get a nice overtime paycheck if you set it up, and donate your time to watching kids while their parents get schwasty.

3. Find holiday party gigs on Craigslist.

While you likely won’t be catering a lot of weddings after October, there are still events to fill the calendar because it’s the season of holiday parties, and some people even go all out for Halloween. Check the event listings on Craigslist, or try to establish a catering relationship at a restaurant. (Find a restaurant that you know caters, walk in at a time that’s not busy, and ask if you can meet the catering manager.)

4. Sell crafts online.

If you are creative, and have been thinking about showcasing your crafts to a wider audience, now is the time, because Etsy gets huge traffic around the holidays. This is a resource that will tell you what you need to know about selling on Etsy. You don’t have to be good at making conventional holiday presents to do well on the site. (Not everyone has to make candles, there’s also a need for design, calligraphy, recipe jars, homemade body scrubs, and anything else you’d imagine that people would buy as stocking stuffer-type presents.)

5. Tutor students through finals using an app.

Theres an app called Quick Helper that connects students with accessible tutors. You don’t need to be a certified tutor, you just need expertise in a subject area that college, or graduate students might need assistance in. To set up your account on the app, you have to chose subjects you are able to tutor in (work experience or a degree in the field is a huge plus), and you set an hourly rate. It’s a lot like Uber for tutors.

6. Pick up a shift on, or near a holiday.

Many employers (whether you work a desk job, or work in retail) need extra hands around the holidays, and you can get the extra cash without working on the actual holiday. One year, I was paid time-and-a-half for working the two days leading up to Thanksgiving, and then flew on Thanksgiving day to see my family. My flight cut costs, and I had just made more than twice what I otherwise would have.

7. Sell your stuff.

If you’re late on rotating your wardrobe, or incredibly late on your spring cleaning, this will make your procrastination worthwhile. Get rid of some of your clothes, by using apps and websites, and get a jump-start on a potential New Year’s resolution by minimizing the amount of junk in your closet.

To sell clothes:

Friends have recommended Poshmark to me. It’s easy-to-use: you photograph your clothing, and give details like size, condition, brand name, etc. and add it to your “Poshmark closet” as one of the items you’re selling. Once you have an account, you can buy and sell on the site.

To sell your books:

If you’re wrapping up the semester, and are strapped for cash, try selling your books. (Even though I graduated over two years ago, I might still have books back at my parents’ house that I should definitely consider selling.) Bookscouter is an app that scans the barcode, so you won’t be stuck plugging in ISBN numbers for days.

8. Find work at festivals, or at a season-specific pop-up business.

In high school, I had a few friends who worked at orchards in the fall. They formed a relationship with the family who owned the business, and were invited back to work during apple season year after year. I understand not everyone has time to make that kind of connection, but I think finding season-specific employment before the holidays is a point well taken. When I got my shifts cut at the winery, I offered to work events (harvest festivals, wine festivals, etc.) most of which happened between September-February. My suggestion here would be to look for craigslist postings for vendors who need an extra helping hand during this season, or find out what falls festivals are happening in your area here.

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