The Life of an Independent Contractor

by Tara Mahadevan

I never intended to be an independent contractor. Frankly, I didn’t understand what the job title meant until I slowly crafted a career for myself, on my own terms.

That, above all else, has been the beauty of working for myself: the freedom. But it took some time for me to really wrap my head around what it means to be an independent contractor. A level of responsibility comes with this career because you have to have your own back; you have to be your own safety net. You have to show up for yourself every day.

Indeed, being an independent contractor comes with its own set of challenges, like zero benefits and inconsistent pay. Because you’re working as a nonemployee, you don’t get the benefit of health insurance, sick days, vacation days, PTO, or a retirement account like full-time employees do.

Pay can be unpredictable—and from my experience, the best way to circumvent this is by locking in a few dependable contract jobs that pay regularly throughout the year. I have one consistent gig that pays every week, and two more that pay monthly and bi-monthly. These jobs are bolstered by other freelancing work that isn’t as steady.

Above all, if you don’t work, you don’t get paid. And while you’re working, you have to handle everything yourself. Unless you have a small team or colleagues, you have to manage your time and workload by yourself (I accomplish this with a handwritten calendar and Google Calendar). Having a monthly budget where you keep track of your income and expenses is another vital tactic to keeping your head above water, as is paying quarterly taxes. This way, you avoid fines (this has happened to me before) and you’re not overwhelmed when April 15 rolls around.

Being an independent contractor made COVID-19 an interesting time. Because I’ve always worked from home and largely from the computer, I thankfully wasn’t affected like so many others. I actually began working for Women Unite! last summer, which has been a gratifying experience.

I, personally, have always been a workhorse, pre- and post-COVID. To be real, I do think overworking myself has been a coping mechanism in the past—and that was just as true during the pandemic. One, you have to pay your bills, and two, sometimes you’re in survival mode, especially last year. The transition to working from home was hard for some, and I think whether you’re an independent contractor or not, COVID revealed just how damaging our work culture is. In America, we live to work.

I think the one thing many people who are independent contractors don’t talk about is how much your work bleeds into your life. This is true for myself, because in addition to working for WU!, I also work in music and entertainment media, where the lines between personal and professional are often blurred. What has helped me is having a designated workspace, like a home office, which has allowed me to step away from work once I’m done for the day.

Over the last 10 years that I’ve been a freelancer, I have learned a lot about what it means to run a business. Because I work from home, I have low overhead, but I still have to pay for certain necessities, like business insurance, or having a CPA that I go back to every year during tax season. I will say that learning about taxes, retirement accounts, stocks, and other investments is critical in general, but particularly as a freelancer. There honestly isn’t enough education surrounding taxes and IRAs, the fact that we don’t have universal healthcare doesn’t make sense, and why employers don’t pay invoices on time is beyond me (cue Solange’s song “Things I Imagine”).

Despite the struggles and hardships that accompany being an independent contractor, I think it’s completely worth it. Building a career from scratch and on your own terms is deeply satisfying. There are freedoms that come with the job that a 9-5 doesn’t allow for—day-to-day-freedoms, the ability to travel, not being tied to a place or desk. You have the opportunity to work in different fields, on different projects, with different people, allowing your mind to stretch in various ways, whether creatively or analytically. Being a freelancer comes with a different level of independence; once you master the ins and outs, you’re golden.