What You Need to Consider Before You Go Freelance : A Checklist

"Chucking the corporate life for the freedom of working independently is the fantasy of many a cubicle monkey. But before you make the jump, ask yourself some hard questions to make sure that you can operate from a position of strength while on your own. Before I joined 99U last fall, I freelanced full-time for five years in New York City, writing for places like ESPN The Magazine, Fast Company, and New York. While I was ultimately able to thrive on my own, the first year was rough. My life was a constant cycle of eeking out enough money to pay my monthly bills, relishing that accomplishment for about as long as it took me to sip a celebratory glass of whiskey and then realizing: This month nearly killed me. How in the world am I going to make it next month? If I were to go back and do it all over again, I’d make one major change to vet the decision to freelance from the perspective of an entrepreneur, and not solely weigh it against my creative ambitions. While it feels clinical to think of your art as a “product”and asking yourself questions about money makes you feel vulnerable, this approach can help you make a decision informed by both creative desires and shrewd business sense. This combination pushes you to pinpoint why you really want to work independently, highlight your shortcomings and hopefully allows you to firm up any weaknesses so you make the move when you’re truly ready. " Matt McCue, 99U, July 2016 Read more