The Trials and Tribulations of a Freelance Writer told through Taxes

Guest Post by Jackson Hille

When I decided to make the transition into becoming a full-time freelance writer, I was filled with self-doubt. I wasn’t a journalism or communications major in college. In fact, I majored in American Studies as an undergrad. But I always had a passion for writing; it helped me blow off steam and it was something I really enjoyed. Being a people-pleaser, though, it was difficult for me to put myself out there. I was afraid of the idea that someone would hate my writing and that I could upset people.Cd2Tl91W0AAcqaB

The first couple of months was really tough, both in gaining self-confidence, as well as supporting myself financially. I had to frequently underbid my competition to land jobs. I’m not even sure if I was making minimum wage for a while. But I was dedicated to growing my client base and really establishing myself as a premium content creator in the world of digital marketing for tech startups. In doing so, my financial struggles continued and I contemplated giving up. My personal finances was a headache; my income was unpredictable, and I realized I didn’t even know how to file taxes as an independent contractor. Luckily, my freshman year roommate, who became an accountant, was really able to help me out and build me into a more effective businessperson.

I learned that there are a few, key differences between filing taxes as an independent contractor versus someone who is on a payroll. As a freelance writer, I was given a 1099 form from all of my clients. The 1099 stated my earnings from each company for which I did contract work, and essentially, my 1040 reflected all of the 1099 forms I received. I discovered that I was also entitled to a few tax deductions as a freelance worker, which helped to alleviate my financial burden. I learned to look out for myself and understand where I stood to gain.

As I became more established, I learned to stop undervaluing my work and realize how much I was worth. I was afraid of losing clients, but through it all, I discovered who was really loyal to me. Looking back, I sometimes forget how much hard work and determination it took to get to the point in my career I’m at today. It’s mostly because I was extremely passionate in what I was doing and because I had faith in myself. Your path may be very similar to mine or the exact opposite, but believe in yourself and you will get to where you want to be.

Jackson - Author PicJackson Hille is the Outreach Associate for FormSwift, a startup that focuses on providing low-cost, online solutions to entrepreneurs and business for all of their document needs. A graduate of the University of California, Berkeley, he has a passion for writing about public policy and sports management when he is not helping individuals and organizations find resources that will create a more efficient workspace. Upon joining FormSwift, he was able to put his full-time freelance career to the side, but he still cares tremendously about helping current freelancers find a stable footing in the Gig Economy, which is why he created the Freelancer’s Essential Guide to Business and Taxes.



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