To Freelance or not to Freelance?

By Mackenzie Rose

In our Democratic society, human needs can be trimmed down to the two most seemingly basic desires: security and freedom. It’s so simple if you think about it, but in this chaotic humanity, it seems so hard to achieve both. As freelancers, you have chosen a life of freedom with little security. Soon, contracts will expire and it will take an effort on your part to find that next job. Poignant as it may sound, miles away there is someone sitting in a cubicle answering phone calls and writing emails who feels secure in his job; yet, he hasn’t felt the sun on his face since he pressed his head real hard against the sixth floor window last week. It’s a bittersweet world out there and we need to pay the bills first and satisfy our needs second. So the question becomes: for freedom or security, what am I working for?

There are certainly issues to consider from both sides of the spectrum. Let’s say you are stuck in a dead end, nine to five job that makes every morning seem like the worst of your life. You’re considering becoming a freelance writer, so you quit your job and get the ball rolling with a new Sologig.com account. You have just left a profession providing security for one of freedom. As David Masello of the Boston Globe wrote of his first freelance transition, “I quickly discovered that it was too early in my career to go freelance. I had few professional contacts at that point and didn’t even know what I wanted to write about. Every night, I would pace the roof of my apartment building, wondering what to do, how to fill the next day.” Before you change your lifestyle, you have to consider what you are doing. Do you have a plan? Will you be able to afford your current lifestyle three months from now?

Conversely, consider the side of a freelance writer, so far work has been good but sporadic and with an excellent string of contracts lately, you are making a pretty decent amount of money. Your friends, however, spend all night talking to you about their jobs downtown and all the contacts they’re making. After a significant dry spell, you decide it is time to leave freedom for security and you begin your job search. You have to question, however, what leaving freedom will do to your aspirations. In that same article from the Boston Globe, Masello writes, “I have made a living as a writer and an editor outside of an office for the last eight years. And there hasn’t been a night where I don’t open the window of my apartment and lean out to look at the city skyline and say, ‘I’m still here, still doing it. I’m my own boss.” Do you want to give it all up? Is security worth your freedom, or better yet, is it even necessary? If you believe you can achieve your desired lifestyle as a freelancer, stick with it.

Freedom and security can seem simple to achieve until you actually try to balance the two. If you are tired of your job whether in a city skyscraper or right out of your bedroom, consider possible outcomes before you make any brash decisions. That big corporate gig may lead to security, but at what cost? Determine your necessary income flow and lifestyle and choose a career path that satisfies your individual needs, whether it is freelance work or not. If you don’t land a contract, or run into a dry spell, realize that with every job, there are going to be rough patches and you may just have to put your head down and work through them. Most importantly, understand what a new job will mean for your wants, your needs and your passion. Always have a plan for paying the bills, but don’t sacrifice your ambitions to do so.