I started freelance writing just under a year ago after spending three years as an editor. A few months into freelancing, I wrote a piece about quitting my job, going hiking and then making more than I’d ever made as staff. Happy ending! I'm now living a four-hour workweek dream scenario and want for nothing.
Not quite. What actually happened was shortly after that piece published, I burned myself out, lost my main contracting gig and had to build much of my income back up from scratch.
I’m going to assume you’ve already done your fair share of googling about how to go freelance and your mind is already filled with the practicalities of it (how much you should have in savings, etc.). If not, journalist Ann Friedman has a great checklist of practical things for the freelance curious to have prepared before taking the leap.
Ultimately, I fell into freelancing, and it took me a while to fully commit. But if I could go back in time and plant some useful questions in my brain, here’s what they would be.
What’s your goal?
The thing about being your own boss is that you are often the only person in charge of your workday. That’s great — and can also be maddening. I spent months floundering because no matter where I was being successful (a new byline, better pay, a cool opportunity), I came up with five more areas in which I didn’t think I was up to snuff (not making enough money, working too many hours, not having as much flexibility as I wanted). I always felt like I wasn't doing enough and often like I was doing worse than I objectively was.
For your first three months, set just a couple of goals — whatever they may be — to be reevaluated at the end of the quarter. They might not be monetary. In fact, I'd recommend that most of them aren't. The goal could be to work from a new location every week or to have every Friday off or to sign a new client or not to wake up to an alarm clock or to say no to projects that go against your moral compass. Whatever it is that made you want to freelance in the first place, make staying true to that one of your goals for the first quarter. You can always change it later.
On a monetary basis, have two numbers: what you need to survive (your minimum monthly income) and your income goal.
One trick I learned from Julie Schwietert Collazo, a full-time freelancer who teaches excellent classes on pitching, involves a little bit of math but is worth it:
- Name the annual income you’d like to make, then divide it by 12, which will give you your target monthly income.
- Divide your target monthly income by four, which gives you your weekly target income.
- Divide your weekly target income by the number of days you want to be working per week, and that gives you how much you need to make per day to reach your big income goal. You can divide that by the number of hours you want to work per day (for example, eight) to see how much you’d need to make per hour.
It sounds simple, but getting down into the nitty-gritty of numbers also helps you decide which projects will be worth your time and which won’t.
Who will pay for your work?
The first four months of my freelancing life were pretty much thanks to a former coworker who was able to pass assignments and even a contracting gig my way. As I wrote for her, I started building up other relationships — sometimes thanks to other former coworkers, other times through cold pitches — which were fundamental when I lost the contracting work.
The reality is, it's tough to get work from clients you've never interacted with before. It's as much about creating quality, relevant work as it is contacting a client at the right time and the stars otherwise aligning. So having someone — or several someones — that you know have work for you before taking the leap will make your transition a lot more tolerable as you start reaching out to unknown prospects.
Where (& when) are you physically going to work?
When someone is offering to pay you, it's hard not to keep saying yes — even if you’ve already been working all day or you had plans this weekend or you were just about to turn off your computer because your head is spinning.
If possible, figure out a place where you can cordon off your work. It might be a desk in a corner, another bedroom, a coworking space or a coffee shop. Then, figure out what hours you’re going to work. I’ve been great about starting work around 9 a.m. each day, but less great about turning the computer off at a reasonable hour. But without these kinds of structures, it’s easy to burn yourself out quickly, which won’t serve you in the long run.
What are you going to do besides work?
You’re going to be in charge of your work-life balance, and it can be really easy to let work become your life. So, what are you going to do besides work? It might dance classes or yoga; it might be a book club or hiking; it could be learning to macramé or reupholster your furniture. But have something to look forward to besides work each week — preferably out of the house. Because what's the point of freelancing if you never get to feel free?