Things to Consider Before You Go Freelance

It’s checklist time, kids, so listen up. No, wait, we mean, start reading. Yeah, that’s the ticket:

behance_05_02by Matt McCue

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 combiniation 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.

Vet the decision to freelance from the perspective of an entrepreneur.

However, it’s hard to know what best prepares one for first year of freelancing without the benefit of hindsight. That’s why, whenever anyone asks me whether they should make the leap, I send them some version of these questions. Follow below and be honest with yourself to assure you’re in a position of strength to make a seamless transition to an independent career.

1. Why exactly do I want to strike out on my own?

If you are considering working independently, have a good reason for doing so. Hating your current role, loathing your boss or feeling exhausted from the long hours all are poor reasons to jet your current job. (You will still experience each of these as a freelancer under more trying and less stable circumstances.) Instead, determine what you can do as a freelancer that you can’t do in your current capacity. Vet the decision to freelance from the perspective of an entrepreneur, and not solely weigh it against my creative ambitions.

Determine what you can do freelancing that you can’t do at your current job

Earning more money is one response that makes sense. Doing something that you love is another, though it’s more romantic than pragmatic. If it is the latter, first see if there is the chance to make your situation at work, well, work. Can you take on new tasks that better fit wth your interests? Can you more thoroughly apply your strengths to the business’s goals? Can you move to a different team that does what you’d like to do more of? The cottage industry of blog posts and books urging us to go freelance can make us think that the solution to everything is quitting our jobs. But that’s not always the best, or even a good, idea.

Try and solve the root of what’s chewing at you you while are you are protected by a steady salary and benefits. (Because jumping into freelance and trying to figure out something on the fly is an income-draining approach.) If you can’t and you believe the only way to accelerate your career is to be your own boss, then…

2. What makes you think you can do better than the people already on a company’s payroll?…

Read it all at 99u