Your Side Hustle Matchmaker: Find Out Which Gig is Right for You

Penny Hoarder web producer Jacquelyn Pica, center, spends some time with sisters, Verity Rabin, 11, left, and Chance Rabin, 10, who she regularly watches in St. Petersburg, Fla. Pica earns between $12 - $15/hour when she babysits.
Penny Hoarder web producer Jacquelyn Pica, center, spends some time with sisters, Verity Rabin, 11, left, and Chance Rabin, 10, who she regularly watches in St. Petersburg, Fla. Pica earns between $12 - $15/hour when she babysits. Sharon Steinmann/The Penny Hoarder
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So you’ve decided to supplement your paycheck with a side hustle.

Congratulations! Now it’s time to determine the best one for you, which may not be as obvious as you think.

We’re here to help. A couple decades ago, locking down a 9-to-5, climbing the corporate ladder and hoping to be called “boss” one day may have seemed fairly standard.

But with shifting job markets, the advent of social media and online marketing, and a booming sharing economy (think: WeWork), people are increasingly thinking outside the cubicle and warming up to the idea of becoming their own bosses. Currently, 33% of Americans are part of the gig economy.

Of course, freelancing doesn’t need to mean quitting your day job today — or ever. There are plenty of low-risk, low-time-commitment freelance opportunities you can engage in to pad your paycheck or test a new professional track.

Matching Your Skills to the Side Gig Economy

First, think about the skills you’ve developed throughout your career and might even use on a daily basis at your full-time job.

Are any of them, like problem solving or personnel management, transferable to other industries? You can even pick up freelance work in the same field as your full-time job, given you’re not competing with your employer or violating a noncompete agreement.

On the other hand, you may be looking to pick up a new skill or take a break from your day-to-day duties after hours. A side hustle can be the perfect way to transition into a new line of work or simply blow off steam while making extra cash.

Browsing online marketplaces, like UpWork and Fiverr, is a great way to find out what kind of services other people are offering to supplement their income. Once you’re properly inspired, let’s figure out which moneymaker is the best fit for your interests and abilities.

You are Gifted With the Written Word

Whether you’re a writer by trade or your diary reads like Shakespeare, there are plenty of freelance writing opportunities that can help pay the bills.

If you’re itching to see your byline in print, try pitching to a website or publication that pays its contributors. If you already have some clips to your name and can track down the email address of an editor at your favorite magazine, go ahead and send them an idea. (I used to be an editor at a women’s glossy, and yes, they really do accept blind pitches!)

But just about every company needs to call upon a wordsmith at some point, and many companies will farm out their website copy, marketing work and blog content to freelancers via online marketplaces.

You Know Your Way Around Web Design

Tons of people have personal websites these days, but not all of them know how to build them. Even content management systems like Bluehost, Squarespace and WordPress can be difficult and time-consuming for amateurs to navigate (guilty!).

Whether you know Javascript, HTML or just drag-and-drop editing, you can offer your services as a web designer through a marketplace like Freelancer or 99designs.

You’re the Go-To Problem Solver

Whether you’re a professional educator or can crack any brain teaser, use your skills to help kids get into college. There’s a huge market for SAT and ACT tutors. List your services on a site like Craigslist, get the word out locally or sign up to become a part-time tutor with a nationwide company like Kaplan.

If you have a special area of expertise — biology, history or even chess — tutor in that subject area. Become an English language tutor for those brushing up on their skills through an English as a Second Language program (you’ll often need certification for that one). Check out for listings.

People Take Your Opinion Seriously

Get paid for your opinion by becoming a mystery shopper. As a mystery shopper, you may be assigned to shop anywhere from Pizza Hut to IKEA. Some mystery shopping companies even assign shoppers to test spa services. After finishing your shop, you’ll rate the company’s service, timeliness, quality and more.

Make sure to research mystery companies before signing up, as many are legitimate, but there are scams out there. According to one frequent mystery shopper, the average pay is $8 to $25 per assignment, plus reimbursement of expenses, but some assignments can bring in up to $60.

Another way to share your opinion is through online surveys, which can pay up to $95 but are usually closer to $1 to $2 each and take about 10 to 15 minutes to complete. One benefit of surveys is that you can complete them quickly from the comfort of your own home. Survey Junkie is one of our favorites — and legitimate! — survey companies.  

You are the Creative Type

We’re all aware of the meditative — and budget gift-giving — benefits of crafting. But you can get even more mileage out of your creations by selling them through marketplaces like Etsy, Artfire and Handmade by Amazon.

Creating goods is only half of the recipe for selling successfully online — you’ll need to also consider the effort needed for promotion, organization and working with customers. We talked to one Etsy shop owner who put a focus on service to grow sales to 70,000 a month.

Dollars Make Sense to You

There’s a profit to be made by helping startups and small businesses craft ironclad business plans. More than 400 people are looking to hire financial experts via UpWork right now.

At UpWork you can browse available gigs like financial planning, executive summaries and marketing strategies, or create a profile and advertise your own services.

You’re a Social Butterfly

Contact your local theater or concert venue to apply to be an usher. You’ll greet people at weekend and evening shows and walk them to their seats. Some ushers even get to watch the events they work. Want your own audience? Casino dealer or product demonstrator are great side gigs that will keep you talking.

Do you host the best dinner parties? Try freelance event planning. Do you ace every interview? Help others prep for theirs. You can meet new people every hour by becoming a driver with Lyft or Uber if you have access to a car that meets their requirements.

You Always Have a Plan

Is your calendar the image of color-coded perfection? Help someone else organize theirs by becoming a virtual assistant. Depending on the employer, you’ll complete assistant duties like scheduling, answering phones, taking dictations and more while getting paid an hourly salary. Check virtual assistant job boards like this one for listings or visit your favorite freelance marketplace.

You’re the First One on the Dance Floor

If you’ve been killing it at the front of your Zumba class, get paid for showing off your moves as a hired dancer at bar mitzvahs, weddings and Sweet 16s. DJs often staff party dancers to fill the floor, so search for gigs through local party DJs or on job forums like this one.

You don’t need any formal training to perform as a party motivator — just a lot of energy, unfettered exuberance and maybe even a mastery of the Electric Slide.


You’re Always Behind the Camera

What can you do with the hundreds of photos on your hard drive? Sell your gorgeous snapshots online through stock photography sites. On Shutterbug, you can earn up to $120 per image download. Or check out this list of other great stock photo sites that pay you for your snapshots.

If You Love Hanging With the Kiddos

If you are responsible and dependable, yet still love to fingerpaint, a part-time nanny gig may be just right for you. One of the best ways to land a babysitting gig is word-of-mouth through friends, family and social media. That way, you’ll have a built-in reference.

Parents also turn to apps like or SitterCity, which help vet nannies with background checks and references. Some of these babysitting gigs pay up to $18 an hour, and your reviews on the sites could lead to more potential gigs.

You Love Fresh Air and Exercise

Take the old-fashioned side gig route and work on someone’s lawn, whether mowing, leaf removal or snow plowing, through the app Plowz and Mowz.

Or, if you want some canine company outside, sign up to become a dog walker with

Still haven’t found your dream job No. 2? Keep in mind that, just like choosing a profession, identifying your ideal side gig can require some soul-searching. But that’s a perk of the process: Meditating on your passions, skills and curiosities can help you figure out what might be missing in your primary career or spark a genius app idea.

The stakes are fairly low because you’re holding on to your regular paycheck while testing the waters. And once you feel like you’ve mastered your new trade, it could lead to a full-time profession you might never have imagined possible.

Romy Oltuski is a New York-based lifestyle writer who contributes to Vogue, Harper’s Bazaar, and The Cut, among others. Browse her work or say hi at