8 Signs That a Career in Freelance Writing is Not For You

Wendy Jacobson
4 min readMay 8, 2019

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Are you one of those people who has been thinking about dipping your toes in the freelance waters for a while but can’t get yourself to take the leap?

You wonder whether or not it’s for you, what it will be like and if you can handle it. And, those questions are stopping you in your tracks from actually moving from thinking to acting.

It is a big step, but it doesn’t have to be. You can start freelancing while you are still at your job, in school or doing whatever it is you are doing. You don’t have to dive in head first and can baby-step your way into to see if you like it.

Before you do, though, you might want to consider whether or not it’s for you. I mean really for you because honestly, freelancing is not for everyone. Sure, there are some perks, but there are also some tremendous headaches, too.

I’ve been a freelance writer for over 11 years, and I am happy to say it is for me. But, I’ve talked with a lot of people who think they want to try it, and once they do they immediately realize it’s not for them.

And, that’s OK. But, sometimes it’s better to find out before you leap. So, to help you determine whether or not a career in freelance writing (or graphic design or PR or social media management or whatever) is for you, consider this:

8 signs that you’ll hate a career in freelance writing

1. You need your day structured for you — If you like to go to your office, turn on your computer, and know precisely what you need to do that day because your boss laid it out for you, then freelancing might not be for you.

As a freelancer, you need to design your day, every day. Your days may differ from one to the next, and you might find yourself with idle time. It’s up to you to fill it because there won’t be anyone telling you what to do and when to do it…except you.

2. You enjoy water cooler talk — If you like to leave your desk and go to the kitchen to stop and chat with coworkers along the way, then you may find freelancing a bit isolating, especially if you work from home. Sure, there will be client interaction, but you will spend much of your time deep in work, or trying to get work.

Freelancing can be lonely at times, and if that sounds daunting, then you may want to reconsider.

3. You hate networking — As a freelancer, you are essentially running your own business. One way to get new business is through networking.

Networking can be a critical part of your business plan because you’ll want everyone you know — and even those who don’t — to know you are a freelancer. That means networking.

4. You do not like administrative tasks — As mentioned above, as a freelancer, you are running your own business. That means keeping track of a lot of details such as your expenses, your mileage, and your business. Luckily, there are plenty of apps available to help you do so, but it’s still administrative work.

5. You are impatient — Sometimes, as a freelancer, you think you have a deal wrapped up. Verbally, the prospect says, “YES” with great enthusiasm, and you are flying high. But then, getting a signature on your written contract, or even a return call or email takes days or weeks, or if you’re unlucky, months. As a freelancer, like most careers, you move on your clients’ terms and timeline, not yours. Patience is a freelancer’s friend.

6. You like, or depend on, a steady income — I’m not saying you can’t make a steady income as a freelancer because you absolutely can. But, it takes time and a whole lot of effort. You might have some months with checks coming in the mail steadily, and other months when you wonder who your next-paying client will be. Not always and certainly not forever, but if you are used to a steady paycheck and don’t want to lose that, then it may be a while before you can leave your day job.

7. You are not deadline driven — Remember, you are working on your clients’ timeframes, not yours. That means when they set deadlines, you need to meet them (and really, beat them, if you can). And, if they don’t set deadlines for you, you need to do so for yourself; otherwise, a project can go on and on and on. So, if deadlines aren’t your jam, then maybe freelancing isn’t either.

8. You don’t like rejection — As a freelancer, you need to look for new business. This means prospecting, meeting with potential clients and submitting proposals. And while it would be fantastic if everyone you came in contact with wanted to hire you right then and there, sadly, it doesn’t work that way.

There’s a lot of back and forth, some negotiating, and some straight-out NOs. You can’t take the NOs personally, because they are not directed at you. They mean that your prospect doesn’t want or need your services now. If you can’t understand that and you take every NO personally, then freelancing probably isn’t for you.

Freelance writing, like any career, is a great choice for many and a terrible one for others. Only you know whether or not it’s for you.

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Wendy Jacobson
Wendy Jacobson

Written by Wendy Jacobson

I love to write and I love my family. I also love to jump rope to music from the 80s.

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