As a full-time freelance writer, I’ve learned to master the art of hustling.
I’m constantly pitching and scouting new story ideas and juggling numerous assignments from my home office.
But writing is a solitary exercise, and I get antsy if I’m stuck inside too long without human interaction. That’s why, for a fleeting second, I entertained the idea of supplementing my regular gig with a part-time job as a driver for Lyft—a ride-share service that I didn’t know much about until the company recently beefed up recruitment efforts in my hometown of Chicago.
Suddenly, online ads were everywhere—in my face, calling my name, teasing: “Wanna make $500 in a weekend?”
Why, yes! Yes, I do!
There was just one problem: I don’t own a car. So I begrudgingly gave up that dream—but I’m still fascinated by those who live it.
In fact, the service-oriented side-hustle economy seems to be plowing full steam ahead given the growing number of white-collar workers like me who are stepping out of their comfort zones to do things like drive Lyft cars all the way to the bank.
Nick Loper, founding editor of Side Hustle Nation, a website devoted to the trend, pins it partly on social-media-driven pressure to achieve something novel—as well as the impulse to hatch an independent venture as a possible fallback in a time when the threat of layoffs still lingers.
“You’ve got to be self-reliant,” Loper says. “Creativity is our 21st-century survival skill.”
Unsurprisingly, creativity just happens to be something these four enterprising—and totally inspiring—full-timers have in spades. Here’s how they’ve transformed their off-hours into an opportunity to support a profitable weekend job.
1. The Music Man
Max Eisenberg, 35, Chicago
His 9-to-5: Vice president and general counsel at a venture capital firm
His Weekend Job: DJ
The Backstory
He may be a buttoned-up attorney by day, but Eisenberg fires up the dance floor at night. Music is his biggest passion and creative outlet, so he parlayed his innate talent for mixing beats into a successful DJ act—as after-hours alter ego Kip Winters.
Eisenberg began deejaying in San Francisco in 2002, but it was only a hobby until February 2013, when he was invited to perform sets at a lounge in Chicago’s Wicker Park neighborhood alongside close friends and fellow DJs Naseem Hasan (a graphic designer who goes by “Old Spice”) and Reggie Thurston (a dentist who deejays as “Mr. Reese”). The night was such a hit that it’s turned into a steady gig.
Reaping the Rewards
Today the trio performs a consistent lineup of weekend gigs throughout the city—and nets between $1,500 and $3,000 a month. But the money isn’t padding their own pockets.
“We all have full-time careers,” Eisenberg says, so rather than keep the cash they’ve earned, Max and his wife formed the nonprofit to which all three DJs donate their earnings. “A couple thousand is meaningful” and makes a big impact for local charities, Eisenberg says.
Their nonprofit, Localized, focuses on helping smaller, Windy City-based organizations like Urban Initiatives, which provides after-school sports programs, and Imerman Angels, which pairs cancer patients with survivor-mentors.
2. The Comedian Cabbie
Kat Ellery, 32, Columbus, OH
Her 9-to-5: Nonprofit community-outreach coordinator
Her Weekend Job: Lyft driver
The Backstory
Ellery loves her full-time marketing position for a nonprofit that provides aid to people with disabilities—even though it doesn’t quite pay the bills.
For a while Ellery worked in catering to pad her income, but eventually realized the hours weren’t flexible enough and the physical labor was too stressful. So she began looking for another source of cash that she’d actually enjoy doing, and luckily, a friend’s recommendation led to a lucrative opportunity with Lyft, a service that pairs citizen drivers with people looking for a cheap alternative to hailing a taxi.
“It’s the best!” Ellery says. “I’m really extroverted, so it’s a good fit for me. Lyft has been a blessing in my life.” Her favorite aspects of her side hustle? Sporting the brand’s signature pink mustache on the front of her vehicle—and, of course, chatting with customers who sit passenger-side.
Reaping the Rewards
Since May, Ellery’s been logging 30 to 40 hours per week, picking up driving shifts every chance she gets on nights and weekends.
And her hard work is paying off: She’s now raking in more cash Lyft-ing than she earns through her 9-to-5 job, and she says it’s possible to reap a weekly reward of about a grand—money she’s using to reach her financial goals. In addition to applying the money to her tax bill and student loans, Ellery is also saving up to buy a home and realize her dream of fostering older children with behavioral difficulties.
But aside from financial security, the Michigan native also clearly relishes the social perks of the gig—particularly the reaction she gets to her original “Cash Cab”–inspired trivia game. Rather than dollar bills, her contestants get glow-in-the-dark bracelets, necklaces, and Starburst for correctly answering questions like, “What job do the Seven Dwarves have?” (Hint: They’re miners!)
“It’s a really great way to pass time,” Ellery says. “It breaks all barriers.”
3. The Baby Whisperer
Dawne Herbert-Withers, 40, Los Angeles
Her 9-to-5: Litigation engineer
Her Weekend Job: Birth doula
The Backstory
Five days a week, Herbert-Withers puts in long hours at a law firm as a litigation engineer, blending computer skills and armchair detective work to uncover the smoking gun in the cases that cross her desk. But in her free time, Herbert-Withers wears an entirely different hat: For the past three years, she’s also operated a successful side business as a certified labor and postpartum doula—with 54 births on her resume to date.
After working with a doula during her first pregnancy in 2010, Herbert-Withers decided to join the ranks of Southern California’s doula community. “I love my husband dearly, but I knew that he could do no good for me” during delivery, she says of her decision to hire a birth professional—an experience that inspired Herbert-Withers to offer that same level of comfort to fellow moms-to-be.
In April 2013, after two years of training, Herbert-Withers earned her certification from the Doulas of North America—and hasn’t looked back. “Every single birth is the most rewarding experience,” says the mother of two.
Reaping the Rewards
Fortunately, Herbert-Withers says her boss at the law firm is supportive of her doula side gig, and it rarely conflicts with her day job, since most deliveries occur overnight when mothers are relaxed. She also schedules prenatal visits with expectant moms on weekends and weeknights.
“I sleep very little,” she admits of her moonlighting. “If a mom sleeps, I sometimes get to sleep, but typically I have so much adrenaline going from being at the birth that I am on second, third, or fourth winds.”
Herbert-Withers takes on one to two clients per month, earning her somewhere between $1,400 and $2,000, depending on factors like travel time and birth location. She using that cash to pay down her student loans and save for her young sons’ college funds. And she’s close to paying off all her credit card debt, to boot.
Once her boys are older, Herbert-Withers hopes to transition her side gig into a full-time pursuit. The reason is simple: For Herbert-Withers, being a doula is her calling, so why shouldn’t it be her life’s work?
4. The Crafty Mom-preneur
Joy Bradway, 34, Fair Lawn, NJ
Her 9-to-5: Software support engineer
Her Weekend Job: Diaper entrepreneur
The Backstory
“I’ve always loved doing crafts,” says Bradway, who discovered her side-career calling several years ago when she began hand-making cloth diapers for her son in the off-hours from her day job.
When she found herself left with an overabundance of fun fabrics with superhero prints from her first batch, Bradway decided to use her scraps to create custom diapers to sell on Facebook and her Etsy store, Joyful Bee Boutique. Her smile-inducing label? Poopsa Daisy.
Since launching in 2011, Bradway has branched out into making knitted wool diaper covers, “wet bags” for dirty diapers, and, most recently, dresses. She gets crafty on weeknights after her son goes to bed, and once in a while will devote weekend hours to making a slew of diapers.
Reaping the Rewards
Bradway’s goodies sell for about $20 a pop, and she makes a profit of $10 on each one. “I don’t have consistent sales, since it all depends on my schedule and how often I am able to find time to make a batch of diapers,” she says, noting, however, that she funnels most of her earnings right back into feeding her “wool yarn addiction.”
But beyond just a way to earn a bit of extra cash, Bradway views her baby-centric business as a fun stress reliever—and an opportunity to save big on expenses she’d be shelling out for otherwise. All told, she estimates that using cloth diapers instead of traditional Huggies-style brands has saved her about $1,000—a figure that’s likely to increase once her second child is born in October.
Since the sex is a surprise, she’s designing diapers for a boy and a girl, and intends to keep the gender-specific garments—then, of course, sell the rest.
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