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15 Women Reveal the Reality of Their Side Hustles

From babysitting to business consulting, having a second job requires discipline, organization, and a whole lot of chutzpah.

By Rachel Simon

Whether it’s babysitting, tutoring, or driving for Uber, it seems like practically everyone has a side hustle these days. In fact, a 2019 Bankrate study found that nearly half of millennials had part-time gigs on top of their day jobs. For most people, the motivation is financial—and, unsurprisingly, that’s especially true for women, with the gender wage gap, childcare costs, and other factors causing 61 percent to work second jobs for the money, vs. just 48 percent of men. 

Clearly, the need is real. But with demanding careers and time-consuming commitments, how do so many of us actually manage to pull it off? We spoke to 15 women with side hustles to find out what they do, when they do it, and how it affects their lives—for better and for worse.

1.

Emily F. Popek, 40s, New York

Main gig: Communications specialist

Side hustle: Freelance writer and Etsy seller

Why she does it: “My own closet was overflowing with things I never wore, so it made sense to see if I could start selling some of those items to make a few extra bucks. I also wanted to spend more time on my own writing.”

How she makes it work: “For most of last year, I was staying up until 11pm or later writing, but I was so tired all the time that I decided it wasn’t sustainable…Now, I usually can squeeze in about an hour of work on weekday evenings while my husband is putting our daughter to bed. The weekends are hit or miss—sometimes I’ll spend the whole morning photographing and measuring clothes or burning through an hour or so on the computer while my daughter plays, but sometimes the day goes by, and I haven’t spent any time on that stuff at all.”

How it affects her: “I don’t really have a social life. I joke that ‘When I’m not working, I’m working,’ but it’s actually true!…Still, I get a lot of fulfillment and satisfaction out of my side hustles, and I have definitely dreamed about what it would be like to do these things full-time. But my husband is self-employed, so we really count on the steady income and health insurance that my day job provides.”

2.

Nikki Prock, 31, Oklahoma

Main gig: English teacher

Side hustle: Online English as a Second Language teacher

Why she does it: “My husband and I started looking into how much it would cost for us to go to Disney World. We do fine on our own, but we definitely only live month to month financially, and I knew there was no way we would be able to pay off a trip in three months. One of us would need to get a second job.”

How she makes it work: “In the summer, I was able to work late at night and early in the morning…However, in September, I found myself falling asleep at 2:30 in the morning, trying to teach a class. Now, I follow a very simple schedule: I teach two classes in the morning before I go to work, and during the weekends, I only allow myself to teach classes during certain hours.”

Why she does it: “I’m doing it because it’s fun and gives me something to do that isn’t just sitting on my couch at home and watching TV. It also happens to be incredibly easy money. The Disney trip we wanted to take? I paid it off in two checks.”


3.

Storm Dolan, 24, Massachusetts

Main gig: Preschool teacher

Side hustle: Babysitter and live-in nanny

Why she does it: “My student loans are insane, so my teaching job barely covers them…not having to pay rent [as a nanny] is helpful, and unfortunately, very necessary.”

Why she does it: “I know that I made the decision to go to college where I did and take on the loans I did. However, I feel that I shouldn’t have to work 3 or 4 jobs to make ends meet. The system of education and job acquisition afterward feels broken.”

4.

Bethany Bentley, 39, Central Illinois

Main gig: Acquisitions editor at a publishing company

Side hustle: Freelance proofreader for the University of Illinois Press

Why she does it: “I began back when I was a just-starting-out assistant editor with a very low salary.”

How she makes it work: “I will typically do my freelance work very early in the morning, before my ‘real’ life and work begin. I occasionally do it in the car while waiting for my kids at their activities.”

How it affects her: “Now that I have worked my way up the company ladder, I really do not need the extra money, but for some reason, I just can’t let it go. It’s a low-stress ‘extra,’ and it’s like a sigh of relief to switch gears from my much-higher-pressure full-time job.”

5.

Caroline Henry, 25, Hartford

Main gig: Account Executive at Ryan Marketing

Side hustle: Pure Barre instructor

Why she does it: “I went through a job change where I was working crazy long hours to working a 9-5 and found myself with a lot of free time.”

How she makes it work: “At first, I was working 7 days a week for almost 8 months and got burned out. I ended up changing my schedule to teaching only during the week (that means starting some days teaching a 6am class and going straight to my 9-5) and keeping my weekends clear to focus on myself, my relationship, and my puppies.”

How it affects her: “I am a people person, and I gain energy from being around people, which I am once I walk through the doors of a Pure Barre studio. I am up and moving and not just sitting behind a computer sending emails—I am able to speak and interact and build relationships with clients.”


6.

Catherine Anderson, 26, Orlando

Main gig: Front desk supervisor at Hilton

Side hustle: Movie theater employee

Why she does it: “I live in an expensive town where one job doesn’t cut it anymore. My girlfriend and I are also planning on buying a house soon.”

How she makes it work: “I work 6am-2pm, five days a week in a hotel, then turn around and work 4pm-midnight three to four days a week.”

How it affects her: “I’m embarrassed when I talk to my friends who don’t live here and don’t understand how tight money is. They think I’m too old to pop popcorn and rip tickets…But I enjoy my side hustle so much more than my normal job. It’s a less stressful, more relaxed, and fun environment.”

7.

Dana Getz, 25, New York

Main gig: Associate TV editor at Bustle

Side hustle: College essay editor for Prompt

Why she does it: “It’s a nice additional cash flow, especially as I’m trying to save money and pay back student loans.”

How she makes it work: “I don’t generally have time to do it except for on weekends, so it often ends up being just an additional task lingering on my to-do list.”

How it affects her: “It’s comforting to have it as a fail-safe considering how unstable and mercurial the journalism industry is right now. Obviously, it would be nice to feel comfortable enough to quit, but I also see it as a reminder to myself of how hard-working and resourceful I am.”

8.

Jamie Gonzalez, 30, Austin

Main gig: Content manager

Side hustle: Social media and media relations specialist for a non-profit theatre company

Why she does it: I was involved with the organization for years as a volunteer. The paid position became available right as I got laid off from my previous job, and then I kept it even when I got a new job—it would be a little extra income from work I was passionate about.”

How she makes it work: “It’s typically less than 15 hours per week and pretty easy to maintain. Everything I do for the role can be done remotely, which makes it less stressful.”

How it affects her: “If I could make a comparable salary doing it, I would absolutely do it full-time. It allows me to be a little more creative than my full-time job does.”


9.

Danielle Washington - 29, Michigan

Main gig: Elementary school teacher

Side hustle: Cashier

Why she does it: “When I graduated, I got a job as a cashier until I found a full-time job, but once I got a full-time job, I realized that it would be extremely hard to support myself on that pay alone. I also owe thousands of dollars in student debt.”

How she makes it work: “I’m constantly working, so any free time I have goes toward running errands or things like that. I also miss out on a lot of family/friend events.”

How it affects her: “I’m a little resentful that in order to survive and have just the basics in life, I have to work two jobs…I’m embarrassed about it sometimes, especially if I encounter people I went to high school or grew up with. I feel like people see me and think, ‘wow, this is all she’s done with her life?’ or ‘I thought she’d be doing more with herself.’”

10.

Ciara Parks - 25, Rhode Island

Main gig: After-School Program Coordinator for a high school

Side hustle: Babysitter

Why she does it: “I was doing a year of service with AmeriCorps and getting a ‘living stipend.’ I had enough money to pay the bills, but babysitting allowed me to have spending money.”

How she makes it work: “I babysit on Saturdays, and I also occasionally will babysit on long weekends or work nights, if the family needs me.”

How it affects her:It can be frustrating to have to work early on Saturday mornings, meaning my Friday nights end earlier. But I love spending time with the kids, appreciate the extra money, and don’t feel as though I am stretched too thin working the extra hours.”

11.

Leigh K. Peterson - 30, Los Angeles

Main gig: Ad agency employee

Side hustle: DJ

Why she does it: “I was feeling unfulfilled at my day job and was looking for a creative outlet.”

How she makes it work: “I have a pretty demanding and depleting job, so finding the energy to DJ after work and on the weekends can be a bit difficult.”

How it affects her: “Through DJing, the sense of alienation and discontent I feel at my job is largely assuaged…If it became financially sustainable, I would certainly quit my day job and pursue DJing full-time.”


12.

Ajah Hales - 34, Cleveland

Main gig: Freelance writer

Side hustle: Transcriber, ghostwriter, Uber driver, graphic designer, and more

Why she does it: “I come from a low-income household, so doing something innovative to make ends meet is nothing new for me.”

How she makes it work: “Some nights I will work until 4 or 5am and not get up until noon the next day. Other times it’s very much like working a 9-5.”

How it makes her feel: “I wouldn’t trade side hustling for the world. Having the freedom to set my own schedule, decide which work interests me and compensates me fairly, get the opportunity to learn about myself, and push my limits has more than made up for any loss of financial stability and security.”

13.

Jessica Doan - 24, Ohio

Main gig: Library employee

Side hustle: Tutor

Why she does it: “I started tutoring mainly for extra income, but also because it’s something I love to do.”

How it makes her feel: “It’s tiring sometimes, but it’s usually just an extra hour added onto my work day. It makes me feel like I’m doing something to help others, and making money from it is helpful to me.”

14.

Jessica Fenn - 26, Los Angeles

Main gig: Nanny

Side hustle: Videographer

Why she does it:It’s passion-based—I’d like for it to become my full-time career in the long run, and financially function as my main source of income.”

How she makes it work: During the weekdays, I work half on the ‘hustle and half at my unrelated, strictly-income job. I work on the weekends as well…but I have to make space for mental health and spending time with friends, or else everything suffers, and I don’t feel like a human.”

How it makes her feel: “Having a job outside of nannying pushes me to focus during the hours I have to give to it, so I’m actually really grateful for that. Sometimes I resent the time I’m obligated to be elsewhere, but it’s making me stronger.”

15.

S. Nicole Lane, 29, Editorial Associate, Chicago, IL

Main gig: Account rep at an insurance company

Side hustle: Waitress

Why she does it: “I was approached by a friend to take on a waitressing shift. As a new mom, it was extra cash and the opportunity to get out of the house and be around adults.”

How she makes it work: “When I get home from work on a Saturday night, I clean up after my son and husband. I load the dishwasher, do laundry. These things are never done.”

How it makes her feel: “I don’t sleep as well as I used to, so getting up early with my son on Sundays is a struggle…But I love the pace, I love food and booze, and I love talking to people…I would love to do it full-time, but the crazy hours would be too much with my son.”

 

Rachel Simon

Written By

Rachel Simon

Rachel Simon is the Deputy Editor at HelloGiggles. Previously, she was the Entertainment News Editor at Bustle and the Wellbeing Editor at Mic. Her work has also appeared in Glamour, Cosmo, Teen Vogue, NBC News, and more, and she's currently working on a lyrical memoir about intimacy. Follow her on Twitter and Instagram (@rachel_simon and @rsimon113).

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