5 Things I Wish I Knew Before Becoming a Freelance Writer

When I first started freelancing, I was a wide-eyed 25-year old with the world at my feet. Women wanted me, men wanted to be like me and every night ended with fish and chips down by the pier (no naan).

“Damn this is easy”, I thought as I cashed the cheque from my 8th assignment in as many weeks. “I can do this all day.”

Nearly a decade later, it turns out my dream career might have more than its fair share of pitfalls. In fact, I might even dare to say that I’m not even sure if it’s a dream job anymore (gasp!).

Freelancing can sometimes be a tough gig. You have to be your own boss, keep up with deadlines, and find good, consistent work. As a freelance writer, I get asked this question all the time: “What do you wish you knew before becoming a freelance writer?” The truth is that it’s hard to answer because we’re all at different stages in our careers. However, if I had known what to expect when I first became self-employed, I would have made a lot fewer mistakes. Here are some of the most important things I wish I knew when I started out.

1) It Can Be Lonely

Freelancing can be a really lonely career. You’re working from home by yourself, and it’s easy to spend a lot of time alone in your pajamas scrolling through Youtube or Reddit communities. Before going into full-time freelancing, you’ll want to make sure you have some friends or family members to lean on when the going gets tough.

2) You’ll Often Find Yourself Working on Projects with People Who Don’t Share Your Skill Set or Work Ethic

This is especially true in my case because I sometimes do political writing. When doing client work for corporations, you’ll often deal with people who have the opposite political views as you. This isn’t necessarily bad; it’s just something that takes some getting used to if you’ve never done it before. A project or two will usually get your head around this transition.

Freelance writing is more lucrative than it’s ever been, but that means you have to compete with more people for work. That’s why I strongly recommend that you diversify your skillset and work on side projects outside of the writing profession. Even if you don’t like math or music, there’s a community out there that needs what you have to offer. Not only can you make some extra bucks, but you’ll also get to meet some pretty awesome people at the same time while expanding your horizons.

3) You Need to Learn How to Say No Without Feeling Guilty or Fearful of Offending Someone

This one can be tough if you’re always eager to please people and become friends with potential customers. A lot of freelancers fall into this trap because they want to turn down any potential jobs. However, when you’re a freelancer it’s easy to get taken advantage of because there will always be someone waiting in the wings to take your place if you decide not to do a piece for any reason.

Freelance writers are always afraid that they’re going to say no to an editor and potentially lose their jobs. But the truth is that if you always say yes, you’re limiting yourself to less money and fewer opportunities. Clients don’t want employees otherwise you wouldn’t have a job; they want contractors who are willing to complete the job at hand to their exact specifications. You can still be polite while firmly asserting your boundaries – it really isn’t as hard as it sounds once you get used to it.

4) Make Sure You Get Paid On Time – No One Likes Waiting for Their Paycheck and It Can Take Some Time for Clients to Pay Up

As someone who has gotten my fair share of bounced checks, I can tell you that getting paid on time is extremely important. Some clients are amazing and pay on time every time, while others have been known to wait months before paying up for what they owe. This isn’t necessarily a bad thing either – some businesses just operate this way out of necessity. However, if you’re the type of person who needs money ASAP, then this might be something that gets under your skin after a few months. Make sure you’ve saved enough money ahead of time so that you don’t go into financial bankruptcy if you miss a payment or two.

There are some editors who don’t even pay their freelancers until they get paid by the client, which means you could be waiting weeks or months to get your money. And while you wait, it’s hard to eat or pay rent. Clients want to pay you cheaply; make sure they understand that if they can’t buy your time, someone else will.

5) Your Social Life Will Stagnate Unless You Make a Serious Effort

Going freelance will definitely change your social life. For example, if you meet new people on the weekends, they may expect you to work regular hours during the weekdays; this can leave you with very little free time. Frequently, I find myself canceling plans because of my hectic writing schedule – but that doesn’t mean I don’t feel guilty. My advice is to make a serious effort to go out with friends and family, even if it’s for an hour or two. After all, freelancing can be a slog sometimes – you need some time off to stay healthy and sane!


Freelancing is a great gig. You get to set your own hours and be your own boss, but it can also be pretty tough at times. I wouldn’t trade my couple of years of freelancing for anything in the world, but if I could go back and tell myself just one thing before becoming self-employed, it would be this: don’t be afraid of saying no.

Oh and make sure you get paid on time!

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