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Working a Second Job? You’re *So* Not Alone

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As of this year, Millennials have become the largest generation in the U.S. labor force, according to recent data from the Pew Research Center. Another, less exciting fun fact: Student loan debt in the United States has increased by a staggering $930 billion since the first quarter of 2004, currently totaling about $1.19 trillion, according to the Federal Reserve Bank of New York. This means student debt is now the biggest source of non-housing debt in the U.S., so it might not come as a surprise that many Millennials have been forced to work double-time, juggling a full-time job and a second, part-time gig just to pay the bills. Some Millennials keep it a secret—not wanting to admit that one hard-earned paycheck isn’t enough to make ends meet—but we’re here to tell you that you aren’t alone. Below, six Millennials share the side jobs that bring in extra cash—and in some cases, have made enough to streamline their schedule.

1. Bartender: “I was a banker working on the Upper East Side by day, bartender by night. Contrary to popular belief, retail bankers do not make a lot of money, so many of my colleagues were holding down two jobs. After closing up for the night, I would quickly change into another outfit to bartend. I kept it secret from my parents because I come from a family of professionals and entrepreneurs, and feared that if they found out I was in a service position to supplement my banking income (a job that college should have financially prepared me for), then it would be clear that a career in finances was the wrong choice. Bartending was the only way to chip away at massive student loan debt, while still paying rent and living expenses in New York. In 7 years, I was able to pay off approximately $140,000 in student loan debt. I’m happy to report that I stopped bartending as of this summer because I’ve paid off all my loans!” —Corina, 29, New York City

2. Dog Sitter: “I actually started dog sitting as a side job for a friend who was in a pinch—she was a dog sitter and had a family emergency, so I covered for her. It ended up being great money and super easy because I’m an animal lover (with my own golden retriever, Rocky!), so taking care of dogs is second nature to me. Helping my friend out every couple of weeks is totally worth the extra cash for groceries and saving for big-ticket items!” —Allison, 29, Stamford, Conn.

3. Confidence Coach: “I’m a licensed independent clinical social worker at a school, working with students ages 9 to 21 with intensive emotional and behavioral disorders. In addition to classroom social skills groups and individual therapy, I also conduct behavior consultations with teachers. On the side, I’m a confidence coach for Millennial women. (I noticed this confidence issue with my friends: highly-educated, ambitious 20- and 30-something women who lacked the confidence to explore new territory in their career or relationships, or even speak up at work.) I have $65,000 in student loan debt, so all of my coaching revenue is used to pay back my student loans and reinvest in my business. And juggling a full-time job with coaching means I have to dedicate nearly all of my free time to ensure a valuable service for my customers. I believe the more successful they are as a result of my coaching, the more successful I will be with my future business!” —Felicia, 29, Providence, R.I.

4. Foreign Policy Writer: “I work for an unfunded San Francisco Bay Area startup, and secretly write foreign policy articles to get by. I am paid below market price with unpaid vacations, and also have to pay for my own healthcare. Unfortunately, living with my parents is a requirement. So, I write articles about foreign policy and international issues, and sometimes use my work hours to do so. I try to do as much as I can outside of work, but sometimes I have to perform interviews during work hours. Even though the articles don’t pay much, they don’t require more than a few hours of work, and I think the money worth the extra time.” —Casey, 26, San Francisco

5. Wine Promoter: “I’m an e-learning instructional designer at a financial services institution; however, on the side, I’m also a wine representative. I started working for a marketing company promoting wine in stores and events during college to earn extra money for living expenses, utilities and groceries. I continued after graduating because I fell in love with helping people pick out wine—and it’s flexible, so I can choose the weekends I want to work. Plus, the added perks (tons of free wine!) are an awesome bonus. I make about $300-$500 per month depending on the season, which now goes toward student loan payments. However, once in a while, I’m able to put it toward ‘fun’ expenses like concert tickets, restaurants, clothes, books and gadgets. ” —Brittany, 29 Minneapolis, Minn.

6. Bar Trivia Host: “I am a marketing director at a healthcare chain, yet I still need to host bar trivia on the side to make ends meet. I wish I didn’t have to, but the extra $500 is much needed. I use it to pay for clothing and all the things that go along with networking and attending events (such as fees and drinks). In a somewhat high-profile job, I also need to keep up my wardrobe and appearance. Without the extra money, I would only have enough income to cover my basic bills, such as my car, student loans, credit cards, and rent.” —Matthew, 30, Boston

Photo: Hero Images / Getty Images


#Unusual Jobs Career Advice
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I'm trying to save a deposit for my first house at the moment and so when a friend recently asked me to help create content for his small business I leapt at the chance. It's going to take some serious organisation skills to successfully manage my full time job and this new side gig, but the idea that I may soon be able to put down a larger deposit than I originally planned feels great! Besides, while having a second job may be a little exhausting, it can look good on your CV and if it involves doing something you enjoy, it's a great way to progress your career without selling your soul.

As a divorcee who had put her career on hold for her ex, combined with living in one of the most expensive cities in the US, I work 7+ days a week between 4 jobs - one full time, one every weekend, blogging for a company, and a few hours here and there at another side job. This pays the bills (barely) and leaves me a little bit for some "fun" money - albeit not much all things considered. I'm hoping my next career move will alleviate some of the financial pressure so I can get a day off every now and then!

Hillary Oneslager
Hillary Oneslager

I'm lucky that I have TWO jobs that I love. My primary job is working for a digital design agency; that paycheck covers all my basic needs plus some "fun" money. I'm also a yoga teacher on the side. I'm very strict about living on the money from my day job and using yoga funds for other expenditures and financial goals. This year my yoga money paid for 2 international trips and I'm poised to have my car paid off in November (as opposed to 2018!) and after that, I'll start saving for grad school. I love having an outlet outside my desk job and am lucky that my second gig gives me the financial freedom to pursue things that normally would take a lot more time and effort to accomplish. If I stay on my current track, I could pay back student loans for the program I'm considering in 4 years instead of 10.

I am fortunate to have two jobs that I LOVE!!! My full time job is working with a company called Boosterthon. I get to help schools and motivate students. I get to be a World Changer and I love it.

Then, 3 years ago, I started my J. Hilburn business. It's difficult, but I love time management and really love my calendar. With a few extra hours a week, I make at least $1000 extra a month. It's the best of both worlds!

I teach tennis as a second job on the weekends. It's easy gas money for my full-time job during the week. My second job teaching tennis isn't "work"...I enjoy is so's a break from the full-time job and the extra money is great!

For over two years now, I've been a full-time long-term Spanish substitute teacher, and I also work at a Boys and Girls Club every day after school and summers (three years ago, I had both jobs plus a third with my county's Parks and Recreation). I currently work 60+ hours/week. I'm EXHAUSTED, all the time. I have 20 minutes between the end of the school day and the start of my Club shift, and sometimes it's all I can do to keep the exhaustion/frustration tears at bay. My boyfriend wants me to quit the Club because of the physical and emotional drains, but I just can't walk away from a job that earns me two student loan payments/month. No matter what I do, I'm constantly in the red and it feels like it will never end.

I LOVE my students and Club kids, with every ounce of my being and calorie burned in energy. But I'm terrified that I'll never be able to break out of the two-job cycle.

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