February 20, 2022

Stuck in corporate purgatory day in and day out, you wind up concocting all sorts of crazy ideas for making a living on your own terms, as your own boss. But unfortunately, selling flotsam and jetsam on ebay or hiring out your services as a mediocre magician probably won’t add up to the green you need to maintain the lifestyle to which you’ve become accustomed.

But if there’s one skill that’s always in high demand and has the potential to put some serious money in the bank without the need for an outside employer, it’s writing. Blog posts, articles, e-books, white papers, and web copy don’t write themselves, and few people have the talent, the patience, the time, or the desire to spend hours on end stringing words together when they could be doing fun stuff like poking out their eyeballs with a sharp stick. Because that’s how most people, it seems, feel about writing: It’s a murderous chore, an excruciating exercise in finding the right words, mastering grammar and usage rules, and wrangling proper punctuation.

But we love writing, and it’s a highly marketable skill. It’s been paying my bills and funding my passions for five years now, but while the idea of freelancing is delicious – ditch micromanaging bosses, set your own hours, work in your pajamas, and get paid good money for doing what you love – the reality is a little more complex. Freelance writing for beginners can be pretty challenging and even scary, once you realize you no longer have the luxury of a day job where you can phone it in when you’re feeling uninspired.

Here are five things I wish I’d known when I first said sayonara to my day job and struck out on my own as a freelance writer. If I had, I may not have spent that first year so stressed out, and things might have fallen into place a little more quickly than they did.

1. Pajamas are a mindset you’ll want to change out of.

You don’t need to put on a suit or anything, but getting dressed in real clothes each morning is a potent psychological tool that can help keep you in work mode as the day progresses. Sitting around in comfy, cozy pajamas all day can hamper your productivity by making you feel lazier than you can afford to be. Before heading to work each morning, put on some clean clothes, brush your teeth, comb your hair, shave your face, put on a spot of lipstick. “Getting ready for work” puts you in the right frame of mind to go get ’em, tiger!, and you’ll feel more like the professional you are.

2. Not having a boss isn’t all it’s cracked up to be.

The good thing about not having a boss is that there’s no one to crack the whip and tell you to get off Facebook and get some work done. The bad thing about not having a boss is that there’s no one to crack the whip and tell you to get off Facebook and get some work done. The thing is, when you freelance, you still have to work, even though there’s no boss to intimidate you into doing it. That can be a challenge, especially when it’s 75 degrees and sunny outside and your tan needs some fine tuning. While you can often get away with slacking off at a day job when the boss isn’t looking, slacking off as a freelancer means that you don’t get paid.

3. The middle man can kickstart your career, but you shouldn’t get too comfy.

Content mills are a great starting place for freelance writers who don’t yet have a solid roster of clients. These companies act as the intermediary between the writer and the client, and they get a cut of the proceeds, which generally means that you’re probably writing for a bit less than you’re worth. Direct communication with clients and editors is rare, and the absence of interaction with other humans can make you feel isolated. Soon, you may realize you’re still just a mere cog, but in a different kind of wheel. And after a while, you’ll probably find yourself longing for professional relationships that make you feel less like a lonely hack and more like a professional yourself. So first thing out of the gate, get yourself a business name, slap up a killer website, print up some DIY business cards, and start putting out feelers for clients of your own. A middle man can provide a welcome sense of financial security in the beginning, but remember that intermediaries go out of business all the time, and that could leave you high and dry.

4. Set a realistic daily income goal and strive to meet it.

Decide how much money you absolutely have to make in a month in order to put food on the table and avoid defaulting on your student loans. Then, decide how much you’d like to make so that there’s also some extra money for the finer things. Divide those amounts by the number of days you want to work each month. The result is the range of income you need to strive to make each day you work. If that won’t get you pounding the pavement looking for clients or staying focused on that ebook instead of catching up on the Twittersphere, nothing will. You may decide that you can quit early today and make up for it tomorrow, but if you don’t actually make up those hours, you’ll be hurting come pay day. If you do make them up, you’ll quickly learn that making up hours makes for a miserably long day.

5. Pay attention to your processes, and refine them constantly.

Freelance writing, for beginners, at least, can start out pretty low-fi. Case in point: In the beginning, I wrote out all of my research by hand. I have over fifty spiral notebooks and a stack of binders full of handwritten notes on everything from American art academies to zoological zoetropes. It took me far longer than it should have to realize how many hours I was wasting not only writing things down on paper, but also having to decode my own shorthand or decipher my sloppy writing. I also spent way too much time manually keeping track of the hours I spent researching, writing, editing, and revising each article I wrote and creating a weekly report to figure out how much I was getting paid per hour. Thanks to the dismal nature of those numbers, I finally got with my game and started actively looking for ways to streamline my processes to free up more time for writing. Nowadays, I copy and paste my research right into the document I’m working on, and I discovered a desktop timekeeping app that perfectly serves my time tracking and reporting needs. From the very first day of freelancing, always be looking for new ways to do things, and you’ll keep unproductive time to a minimum during your work day.

BONUS: Let everyone know you have a “real” job from the get go.

Somehow, when you’re self-employed and work from home, some people think that this means you’re totally free to help out with the bake sale fundraiser for school, have a leisurely telephone conversation about weekend plans, or take the car in for an oil change and tire rotation. Here’s a newsflash: You don’t have time for any of that during the day if you want to make a living as a freelance writer, because making a living requires having a job, and in most cases, the ideal time to do that job is during daytime hours. If you don’t do your job during the day, you’ll be doing it in the evening, while the rest of the family is eating dinner and watching a movie, or you’ll be slaving away late at night when everyone else is in bed. So here’s my last tip: Don’t tell people that you “have to write.” Tell them you “have to work.” It seems like splitting hairs, but when you say, “I have to write,” they’re probably imagining you sitting in a recliner with your laptop propped on your legs, dreaming up clever little stories and having a lovely, leisurely day of it. When you say, “I have to work,” they’re more likely to imagine the reality, which is you furiously hunched over your keyboard trying to meet a deadline while four more loom nearby.

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