I've talked to many writers are either do all their writing for an employer or moonlight with a little part-time writing here and there. Some of them are happy with their current situation, and some aren't. The ones who aren't often express their wish to go freelance, but always follow up that wish with phrases like "I'm still weighing the risk," or "I know I could do it, but I'm scared to make the big leap."
Perhaps you've been toying with the idea of offering your writing (or other) services on a freelance basis, but something always seems to hold you back. Maybe you've gotten used to a comfortable existence that could well suffer upheaval; maybe someone is constantly in your ear about why you shouldn't bother; or maybe you're just waiting for all the planets to line up and spell out your marching orders. It's true that freelancing involves risk -- which means that on some level, you've got to be a risk-taker. Here are some thoughts on how to see risks for what they are (or aren't) and control what you can control.
There's Never an Ideal Moment to Go Freelance
If you're waiting for that perfect moment to take up a freelancing career, you'll still be waiting when they stuff you into a pine box. There's no such thing as the perfect time to uproot one way of life for another, especially one as potentially unstable and stressful as freelance work. But there's also no perfect time to get married, have a baby, move across the country, or undertake so many other major life transitions. In the end, your desire to do it has to be strong enough to outweigh potential risks and obstacles. Having said that, you might decide that layoffs in your workplace or some other unsettling issue provide a reasonable trigger.
You Can Reduce Your Risk Up Front
While the risks are real, so is your ability to minimize it before you make the leap. For starters, keep your relationship with your present employer and co-workers solid, just in case you have to ask for some job placement assistance someday. At the very least, don't burn your bridges (or a bagful of dog poop placed outside your boss's door). Any professional network is a potential gold mine for future connections, whether you're freelancing or returning to the 9-to-5 world.
Next, examine your current lifestyle. If you're just making your monthly nut on your current handsome and predictable salary, then you'd better downsize right now. Move to a smaller place, get rid of that extra car payment you could probably live without, stop dining at restaurants every night, et cetera. Live as if you're poor -- because there are times when you will be. This downsizing not only helps to buffer you against financial swings, but it also forces you to think more carefully about how you handle money, a critical skill for any business owner.
Not All Naysayers Are Qualified to Say Nay
In the minds of some, there's never a good time or sufficient reason to take a risk -- any risk -- and an infinite number of reasons not to do so. These are the folks who tend to reply to your every argument for doing something with "Yes, but..." Don't fall into the trap of defending your position against this brand of naysayer, because there aren't enough counter-arguments in the world to shoot down the list of objections they seem to carry around in their shirt pocket. Instead, think hard about who's doing the naysaying, and why.
Ask yourself: Do they actually know anything about freelancing at all? Do they just play it safe in all aspects of their own lives by nature? Did they actually try freelancing and fail at it -- and if so, did they make specific mistakes that you could easily avoid? Is there some other hidden emotional agenda at work? Are some of the arguments legitimate? Are you the naysayer? Analyze the source of the naysaying, and you'll know what portion of it give due consideration and what portion to ignore.
Of course there are other factors in considering a freelance career, such as whether you can thrive in isolation, maintain a sharp mental focus, and summon the necessary self-discipline to complete projects on time (and sometimes under pressure) without a supervisor. But for many writers, it comes down to how willing or able they are to roll the dice. In the end, no one can else can make that call for you -- but the more you understand about the risks involved and how to address them, the better informed your choice will be. Good luck!