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Are You Ready for a Freelancing Career?

On your mark. . .

Photo: Andrew Neel

Is freelance writing worth it?


Is freelance writing a good career?


Is freelance writing for me?


Have you asked yourself those questions before? If you have, you’re not alone.


Obviously, at Contena, we think the answer to the first two questions is a big YES, but we can’t answer the last question for you.


But since we know it’s something you might be thinking, we wanted to share some thoughts with you.


If you’re reading this post, maybe you have some doubts if freelance writing is right for you. Maybe you’re wondering if you have what it takes. Here are a few reasons that freelance writing may not be for you, and what you can do about it to push through those potential pain points.

Freelance Writing May Not Be For You If…

1. You struggle with independence

Seriously, it sounds amazing but freelance writing and the independence it brings isn’t easy for everyone. Some people need regular check-ins and accountability. And often, you’re not going to get this.


As a freelance writer, typically I send a pitch (or have a post pitched to me by an editor I work with) and we agree to the terms: pay, length, due date, etc.


Then I get to work.


When the post is due (or earlier when I can), I send it in. I also make sure to correctly submit for payment.


Editors probably won’t chase you down (and they shouldn’t have to) for your post, your edits, or whatever they need to process your payment.


I love that I can get things done in my own time and that I control my schedule (to a point), but for some people, this independent work environment may be challenging.


What’s the fix?


So here’s the thing-- even if you’re used to working in a more traditional environment and that the ongoing check-ins are necessary for you to get your work done, you can still make the transition to freelance writing.

Try these ideas:

  • Set times in your schedule to work, much like you would a meeting. Don’t break the appointment with yourself.
  • Create internal deadlines for each project. For example, decide when you want to have the outline done, and when the first draft is due. These short-term goals for each assignment may help keep you on track.
  • Find an accountability partner. Team up with another freelancer (or someone else you can count on) to check in with regularly. Maybe you each commit to a daily afternoon check-in to see how work is going. Knowing that you have to report to someone else will hopefully help create more structure and help you follow through with the tasks you need to complete.

The independence that comes with remote work is fantastic (for most of us), but it can take time and energy to make sure that you use this independence to your advantage and complete your assignments and tasks on time (and without stress or procrastination).

2. You don’t like working from home in your “cozy cozies”

Related to the idea of independence, when you’re a freelance writer (or any type of freelancer, really), you can work from wherever.


This means you can work from home, a coffee shop, your car, while on vacation… The options are endless.


And so is the attire that you can wear while you complete your work.


In our house, we spend a lot of time in our “cozy cozies.” Since I work from home a lot, that’s pretty much my work uniform.


What are “cozy cozies”? They’re articles of clothing that just feel good: they’re cozy. Think sweats, pajama pants, cotton shirts, baggy sweatshirts, and fuzzy socks. Generally, the pants that don’t include a zipper or button.


You get the idea.


I do get “dressed” most weekdays because I take my kid to school, but knowing I’ll be back home to work, I put on my “outdoor-appropriate cozy cozies,” like cotton jogger pants (I love Old Navy for these!!), and a cotton shirt or sweatshirt.


But basically, I’m in cozy cozies 90% of the time.


Though I love working this way and I know a lot of my fellow freelancers can relate, some people can’t work like this. You might be the kind of person who wears jammies and then just hangs out. Bye, bye productivity.


Or maybe for you, working from home would turn into doing chores.


If you’re shifting to work as a freelancer, you might struggle with some of the casualness that freelancing brings to your “office” and your work attire.


The location and the attire we work in can affect our mentality, so be aware that you might not be able to work from home in your jammies like much of the freelancing workforce does.


That might not be your jam(mies).


Can’t work in your cozy cozies?


That’s okay. Take the time to figure out what would be a good “freelance uniform” for you.


Maybe you need pants with a zipper. And shoes.


Whatever outfit is helpful to you getting into work mode? Wear that! You might want to “suit up” for work, even if you’re at home. Whatever gets you into the freelance frame of mind? Wear that!!


What about if you struggle with being productive at home?


Again, don’t stress and don’t shy away from freelancing because you know you can’t work from home.

You have options for where to work!

  • Try a coworking space. This might give you the feel of the more traditional work environment that you’re used to, which will feel more conducive to getting work done.
  • Find a local place (think a coffee shop or restaurant) that you can set up shop. For some people, these locations will be too noisy or distracting, but for others, getting out of the house is all they need.
  • Visit the library. Your local library will have at least a few options for spaces available to you- some will even be private where you can close the door and get to work. Check out your options and if you have a few libraries in your area, visit each one out and see what works best for you.
  • Hang out at work longer. If you’re still working a traditional job (and your boss would okay this!), get to work a little early or stay a little late to get your freelance writing work done from that location. Again, make sure your boss is cool with this, but for some, this can be a great solution.

Being a freelancer allows for more flexibility and casualness in what you wear and where you work. But, if those realities create challenges for getting the work done, change it up and find the attire and the location that lets you get your best work done.

3. You don’t like writing

I’m going to be honest. This one’s a little harder to get around.


You might want to be a writer because you feel like you have ideas, stories, or knowledge that would be great to share with others. And, much of what we share these days is through our writing (though you could always start a podcast!!).

So, you might really like the idea of being a writer.


But, maybe you also don’t really like writing all that much.


Does that mean you can’t be a freelance writer?

Well…If you want to be a writer, you should probably like writing. At least a little. Because otherwise, you might find that you want to give up even though you have a lot of things to say.


But, is your writing career doomed? Maybe not.

What’s the fix?

  • If you have ideas but don’t want to write, consider voice recognition software and apps, or check out this hack to use with Google Drive. This way, you can get your first draft down a little more easily, and can edit from there.
  • Take a course or read a few books for freelancers. You might be rolling your eyes at this. It’s probably high school or college English courses that lead to the dislike of writing. But now is the time to learn about writing on your terms, with the purpose of helping further your career. With this type of freelancer motivation, you may find this learning enjoyable and it can kick start (or reignite) an interest in writing.
  • Hire some help. Now, this may not be the best option, especially long-term, since you want to make money, not just spend it. But, in some cases, it might make sense to work with a writing coach (Don’t forget to take advantage of your Contena Coach!!), or possibly hire an editor to help before you submit your work.
  • Remember that writing is a skill and the more time you do it, chances are, the better you’ll get at it. The better you are (and the more efficient you are), your enjoyment might go up too.

So yeah--disliking writing might be hard to overcome, but it’s not impossible.

In conclusion…Is Freelance Writing Right For You?

Here’s the thing- we still can’t answer that.


But hopefully we’ve shown you some of the potential reasons why freelance writing might not be for you, and what you can do about them.


Even if you’re mildly interested, go for it! There’s not a whole lot you need to get started and you never know where freelancing will take you.





Originally published by Sara Robinson.

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