When DIY freelancing goes wrong

Nov 28, 2016

It never fails to happen. When I reconnect with a former student or colleague, the question of, “So, what are you up to these days?” comes up.

Such was the case a few days ago when I met with a former student for breakfast.

“I am freelance writer now.”

“Sweet! You get to work at home in your pajamas.”

“No. I prefer yoga pants.”

We both chuckled because she knew me from my tailored suits and high heels days.

“Would you do it again?”

The question was innocuous enough, but it did cause me to pause. Rarely, if ever, does anyone ask me that. I guess because most of my peers are my age, they understand the nuances of secondary and even tertiary career shifts, but looking into the eyes of a bright-eyed, corporate, 25-year old melted a layer of defensiveness and I answered as honestly as I could.

“Yes, but there are so many things that I wish someone had told me before I started freelancing.” And thus, our conversation became the inspiration for this article.

When contemplating the world of freelancing, many of us think about the freedom that comes with it, the flexibility of working from home or a coffee shop, and the ability to carve out a work/life balance that some of us never experienced in previous lives. I loved the idea of being able to write and being able to work remotely, literally, from anywhere.

Yet, for all of the joys of doing this work, there are a few egregious missteps that I made and that I have seen others make that can be avoided by having a firm understanding of the following: Doing-It-Yourself (DIY) may work for building a trench in the backyard or adding backsplash in a kitchen, but you may want to rethink DIY when it comes to being a freelancer.

Prior to leaving an anchor institution, my experiences revolved around teaching others the joys of reading and interpreting literature and the merits of expressing oneself in writing. Throw in a few ancillary responsibilities and that was the extent of my professional life. All of my degrees are in English. I never took a business class—not even as an undergraduate. I never had to. My entire life was mapped out by someone’s HR department, accounts payable office and business management team. Understandably, and perhaps arrogantly, my biggest concern was with keeping up with my bi-weekly paycheck.

The minute I transitioned from being paid by someone else to paying myself, my world turned topsy turvy. Suddenly, spending hundreds of dollars on a purse seemed foolish. Treating my friends to an elaborate dinner, just because, became a bad investment. And getting a new car simply because that year’s model had an extra exhaust pipe became laughable. In other words, I started to see money, my spending, and my professional aspirations through a different lens.

For the first few years, I struggled because I only wanted to focus on the creative side of writing. I wanted to create art for art’s sake. In the meanwhile, I still had fiscal responsibilities that needed to be met. Stressing about paying my bills and keeping the lights on created anxiety and stress and before I knew it, my writing suffered.

DIY was going horrible wrong.

After almost finding myself in financial ruin and on the cusp of looking for a full-time job, I did what I should have done from day one. I finally came clean with myself and admitted that I did not fully grasp the commerce side of writing. My business acumen was in need of retooling and I needed help in doing so. Being a neophyte freelancer was like being a one-woman business entity without understanding the rules of engagement.

I started to study my industry. How much did other writers and editors charge? I discovered that I was not charging enough. I met with my accountant and we began projecting my 12 month cash flow: costs, expenses, revenues, and shortfalls. With the advice of legal counsel, we created contracts, invoices, and other documents. At the advice of another friend, I started leveraging the LLC that I created years before—although this may not be a viable option for all freelancers. I also started an email list and learned the value of branding and promoting my freelance writing on social media.

I started reading books by business industry leaders and I even took a few online self-study classes for entrepreneurs. My right brain lamented that she was tired of my left brain getting all of the attention.

Having an infrastructure and a team has turned everything around. I am still learning, but now, I really can focus on my craft because I have a system in place that allows me to ebb and flow as a freelancer.

There are those who may believe that once freelancing starts to feel like a pseudo-corporation then you are no longer a real freelancer—somehow the essence of your craft is diluted. From my personal experience, that train of thought actually pushes freelancers back into traditional jobs. It prevents well-meaning freelancers from fully embracing their ability to benefit from the commerce side of their art.

Instead of creating an arbitrary either/or dichotomy, I have another suggestion, especially for writers: You can practice your craft, be impassioned about your subject matter and get compensated for your writing—just be careful of DIY all by yourself.

Tyra Seldon

Tyra Seldon is a former English Professor turned writer, editor and small business owner. Her writing addresses the intersections of race, gender, culture and education. seldonwritinggroup@hotmail.com