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“I Get Paid $1,700 to Wine and Dine Friends”

All work and no play? Side-hustling sisters making money by entertaining, crafting, working out and more show you how to cash in on your passion.

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illustration of hands serving wine holding jewelry doing exercise side hustles
Noopur Choksi
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Sisters work hard for the money. And when we need some extra cash, we find creative ways to pay the bills. For example, to supplement my freelance writing career (and because I love cats) I became a cat sitter. I generate business by distributing my eye-catching cards to local coffee shops, pet stores and veterinarian offices, and I hand them out to folks I see with their cats in tow. I post candid shots of my adorable cat clients on my social media pages, and several cat moms have hired me after seeing my profiles on Facebook and on, a free localized social networking service. Holidays are my busiest cat-sitting periods, and last year I made $700 just from cat sitting Christmas Day through New Year’s Day. Want to start your own pet sitting business? Check out sites like and, which connect owners with vetted sitters.

When it comes to turning a passion into a side hustle, I’m in good company. According to a report from Bankrate, more than 44 million American adults have one. Check out these three entrepreneurial sisters who are getting paid to do what they love, and pick up some tips for turning your passion into profit.

Donyale Smith, 47
Day job: Deputy director
Side hustle: Wine consultant
Additional income: About $1,700 a year

Monday to Friday, this Baltimore, Maryland, native works at the Department of Veterans Affairs. But on weekends, she loads up her car with cases of Cabernet and Chardonnay and hosts private wine tastings in clients’ homes as a consultant for Wine Shop At Home. “After the wine tasting, guests place their orders and the wine is shipped directly to them,” she explains. To sign on with this commission-based side hustle, the enterprising working mother purchased the company’s business kit and went through a training program. And it’s not just her income that’s expanded — the casual wine drinker who once preferred sweet reds says both her palate and her social circle have broadened, too. “I get to meet a wide variety of people from all walks of life, and every tasting has a different dynamic with [different] personalities. Wine makes everything more fun!”

How you can get started: Apart from Wine Shop At Home, there are several other multi-level-marketing (also called network marketing) wine companies, such as Direct Cellars and Travelling Vineyard. To get started, sellers either purchase (at a discount) a specified number of bottles that they re-sell themselves or they purchase sampler kits to be served at tastings. Customers’ choices are typically shipped directly to them from the company, and the seller makes a commission. Carefully research any company you’re thinking about doing business with. The Federal Trade Commission cautions that not all network marketing programs are legitimate. And out-of-pocket costs for training, inventory or marketing can add up. Learn more by searching “multilevel marketing” at

Keys to success: Social media is an effective way to reach a wide audience with minimal resources. And, as always, word of mouth is key. So leverage all your contacts, every client, acquaintance, friend, family member, coworker, teacher and mentor.

Katrina Charles, 41
Day job: Executive assistant
Side hustle: Jewelry designer
Additional income: About $500 a month

When she was laid off from her longtime gig as an executive assistant in the financial industry, Charles turned lemons into lemonade by launching her handmade jewelry business, Pieces of Wisdom. Now the stylish mother of three sells her Afrocentric and eye-catching earrings, bracelets and necklaces – made from fabric she finds in African markets and on her travels – through Instagram and Square. To attract clients, Charles proudly wears her wares. “I am walking advertisement,” says the Brooklyn, New York, native. “My customers usually find me by asking where I found my earrings. I also get many customers via word of mouth. Referrals are everything!”

How you can get started: Setting up shop on an online marketplace such as Etsy, Shopify or Square isn’t hard; just follow the step-by-step seller directions posted on each site. Your shop name, however, is crucial. Be creative but make sure the name reflects the products you’re selling and is easy for clients to remember. And when you post your items, always include several sharp, high-resolution photos that show your wares from all angles.

Keys to success: A side hustle isn’t simply a hobby. If you’re going to charge for a product or service, it needs to be of high quality. Choose something you know you’re good at so you can build a strong reputation through positive customer feedback.

Lottie Joiner, 46
Day job: Editor
Side hustle: Fitness instructor
Additional income: $300 a month

She has a demanding full-time job with the NAACP in Washington, D.C., but this fitness enthusiast finds that teaching Jazzercise classes in her spare time not only helps her to stay fit but also to de-stress. Joiner took classes for five years before she became an instructor. “I decided to teach because it’s fun. For one hour I don’t have to think about deadlines or work. Also, I no longer have an excuse to not work out.” Now she teaches the dance/fitness class up to four days a week at schools, churches and community centers in the D.C., Maryland and Virginia area. “I love looking out at my class and seeing people of all ages moving, laughing, dancing, working hard and loving it. I have a student in my Sunday class who turned 80 years old last year! This inspires me.”

How you can get started: Many trainers study for certification by either the American Council on Exercise or the National Academy of Sports Medicine. Once they’ve completed either of the self-paced programs, they are equipped to work with clients privately, at fitness centers or in medical and corporate settings. NASM’s programs begin at $700; ACE’s at $300. and

Keys to success: Time is money, so make sure that your side hustle is not only something you enjoy doing but also worth your time financially. Research the going rate for your product or service in your area and price accordingly. When you’re just starting out, you may want to charge a bit less, and then increase your prices as you gain a following of repeat customers.