So, you decided – you’re going to work freelance.
You’ve been toiling away at your outside job and pecking at your writing if time allows, but lately you’ve chafed at the lack of creative forward movement. You long to toss in your resignation with a self-satisfied, “No, I’m not going anywhere else, I’m working for myself!”.
In your mind’s eye, you picture yourself ensconced in a restful cabin in the woods or at your desk before a fire in 
a converted castle or wearing flamboyant shirts you don’t care if anyone likes while writing on a tropical beach somewhere. No more bosses, no more rat race, no more commuting – nothing but letting loose the dogs of your creativity and all the while the money keeps rolling on in, right?
I hate to break it to you, but the reality of quitting your day job to work full-time as a freelance writer is often far from those pleasant fictions. Many a talented writer has crashed and burned going full-bore at a freelance career and it was for no other reason than lack of preparation before making the leap.
If you’re seriously considering going freelance full-time, there are a number of important considerations you should mull over before deciding it’s the right call:
You have experience and a reputation
Contrary to popular belief, it takes experience and a reputation to get good freelance jobs that can support you. Even experienced writers struggle in the freelance market. If you’re not already a semi-experienced writer before you go down that road, it’s going to be tough or near impossible.
If you’re in the other camp, one of the wannabies who think you can quit your day job and learn to write as you go, I hate to break it to you, brother, but you’ll be competing for jobs against the likes of me and the rest of the professional freelance writers who can write circles around you in our sleep and who already built extensive industry networks over years. We can often get jobs on reputation and word-of-mouth alone without having to send samples or a portfolio. Can you?
Before you make that leap and cut off your only source of income, a better use of your time would be to get focused. Writing is art and it takes sacrifice. While you’re still working your other job, ensure you carve out time to write every day and get polished and published.
If you can’t do that? You don’t have the discipline to work freelance.
Be smart. Take on small, piecework freelance jobs and build your reputation that you can use to broker bigger jobs later. Get your name out there. Working a full-time job while writing on the side is where you pay your dues, convert feedback into implementation, and hone your craft. Build your portfolio and your web presence. If no one knows who you are, they aren’t going to pay you gobs of cash for anything and you’ll be broke and back in your parents’ basement with your tail between your legs before you know it.
You’ve built your professional portfolio
At the beginning, it’s nearly impossible to pick up freelance jobs without samples and credits, so you’re going to have to start small. Earn writing credits and that means professional writing credits.
You can post to your blog all your want, but if no one’s ever paid you for writing any of those articles, even a small bursary or honorarium, those eloquent blog posts about cats or your editorial commentary on global warming aren’t going to get you very far.
Having a blog is an excellent way to bulk out your web presence, to add to your reputation, and the posts can be used as style and skill samples, but none of that writing is considered a professional credit. A professional credit is counted as writing you were paid for and that was published by someone other than yourself. Keep that in mind if you’ve been spending all kinds of time on your blog and not submitting anywhere. In rare cases, someone may have an incredibly popular blog with millions of followers and in that case, you could use it as a credit notation, because it demonstrates you already have a large following which brings a guarantee of some readership and return on investment. Most people don’t fall into this category, though, so you’re going to have to submit.
If you’re trying to get your first novel published and in the query letter can’t quote anything professional published under your name, most big publishing houses aren’t going to take a chance on an emerging writer who no one has ever paid money to. You may well be an excellent writer and it’s not a judgement of your abilities. This is an economic reality where they’re not going to invest large amounts of money in someone who they can’t judge by experience is going to give them a return on their investment.
Give yourself a leg-up before you quit that day job. Spend time submitting and earn some pro credits you can cite in your query letters toward more lucrative professional work.
You have money put aside to float you
Like any business endeavour, you’re going to need money to begin. Becoming a full time freelancer is your business, so invest in yourself. You’ll need to have the capital up front, enough to float you through the growing pains. Most small business fail in the first or second year and freelancing is no different. How will you live until the money starts flowing?
Be practical and sit down and work out your budget. Factor in the cash you’ll need to cover all your necessities like rent, groceries, Internet, cell, dues to your local writers guild and whatever else you need until your jobs are overlapping and the money flow evens out. A good guideline is to put back what you need to live for three to six months, but honestly? It’s always safer to have more, because you just never know.
Even in the best of circumstances things can go wrong. Help yourself out and make sure you have some cash in reserve for things like an emergency wisdom tooth extraction or a 3-day power failure that wipes out everything in your deep freezer that you bought ahead (true story – happened last winter during a hellacious ice storm here to the tune of about $2000).
Shit happens, but with good forethought you can save yourself from disaster by working up a little nest egg before you quit your day job.
You already have your jobs lined up
Be smart and spend time picking up jobs with different deadlines and start working through them while you’re still working your full-time job. Anyone who’s ever been out of work knows how tough it is to find a job and working freelance full-time is no different. When your existence is hinging on those jobs, don’t leave finding them until after you already cut-off your only source of income.
If you’re already working through and getting paid for some of those piecework jobs when you leave work, the transition will be much smoother and you’ll already have some money coming in, so you don’t blow through all your savings in the first couple of months. Without jobs lined up, the stress of not knowing where your next dollar is coming from will crush you and you won’t be able to be creative or stay the course.
You already changed the way you live
Be prepared for the reality of the change to your life. People often labour under the mistaken impression that they’ll have all sorts of free time, but this may not be the case, not unless a miracle happens and you sell several large things in a row right at the beginning. You’ll be working to multiple deadlines and will need to ensure you’re budgeting your time well to get through them all. More than likely you’ll be working longer hours than you’re used to – challenging when balancing your career and your personal life.
As a full time freelancer, you also have all the considerations of a small business which means you’re wearing a lot of hats – doing bookkeeping, correspondence, filing, banking, looking for more jobs, marketing and whatever else you need done in a day, in addition to working at your writing. If you’re lucky and have a supportive significant other, they may be able to help you with some of this to free up more of your time for composition, but not everyone has this luxury. Be prepared for multi-tasking and with being disciplined about your days so you can fit everything in.
With luck, you worked up a realistic budget and have already adjusted your spending habits to accommodate a reduced income in the early days. If you haven’t given any thought to this, remember, you’ll be working with a lower income at the beginning and you may have to make some sacrifices. Things like that weekly trip to the bar or movie with friends might need to become having them over for movie night instead or changing your daily take-out food habit into cooking dinner at home to help you make ends meet. While you’re working up your budget, you should look at the ways you can scale back your lifestyle.
You fucking love it
Seems like a no-brainer, but I’ve had people complain to me about how much they hate writing and then still think it’s a good idea for self-employment. What???
Seriously, dude, you could have a thousand freelance jobs lined up, but if you hate what you’re doing, it’s going to show in your writing. People can tell and it turns them off. If you don’t love it, over time, you’re going to find it difficult to force yourself to keep going at it every day. And you’re not going to last long.
Working freelance can take many shapes, so if you fall into this category, you should think about applying your energy toward something you actually like. That way you can still live the dream without torturing yourself.
People who are successful as full-time freelancer writers are among those lucky few who love what they do for a living. If you want to be among those who make it, practice your craft, accumulate a few professional writing credits, and be practical and plan for the lean early days before telling your boss to suck it. You stick to that? You’ll be well on your way to achieving your dream of…
What’s that phrase again boys and girls?
Supporting yourself on your art!