It’s just as important when you’re thinking about making a career transition or starting a side hustle to consider the negatives of what you’re going to do as well as the positives. It’s so easy to find marketing materials about all the upsides of being a freelance writer. And don’t get me wrong- I love what I do. But if you’re not careful, it’s easy to get excited about a career that also has its challenges. What I find to be great about freelance writing is that you can navigate these downsides when you understand your underlying mission and your drive to freelance.


Why Focus on the Downsides of Being a Freelance Writer?

Now some people might react to that comment and say, “Negatives! What’s the point of talking about the negatives? The positives will far outweigh it.” Well, as any entrepreneur knows – and really any person knows who’s dedicated their life to doing something that’s a little bit off the beaten path or rising to the cream of the crop – there’s always going to be negatives with anything and what makes you different when you make a transition into freelancing is whether the negatives work for you. What do I mean by that?

In some situations, you’ll be able to cope with the negatives. You’ll be able to overcome these negatives or at a bare minimum, you accept that they are just part of the bigger journey. Now sometimes you’ll be in a situation where the negatives are really really overwhelming. They really bother you. So for me, that would be working in an office situation where I’m being micro-managed and have zero say over what I’m doing every single day, and I’m just sitting at a desk between the hours of 9 and 5 because that’s what my boss tells me to do. That would drive me absolutely crazy. So I know that it’s not the right fit for me.

The negative of that particular job is not just a downside, it’s an extremely big downside and a really problematic one. Now there are downsides to freelancing too. So you got to figure out, are these things that I could cope with? Would these be a major annoyance? Would these be something I could come up with a plan to handle or will I be able to go in with an open mind and realize they are just part of the proposition of being a freelancer?  

Here are my most common “downsides” of being a freelance writer.


You’re Going to Be Alone a Lot

It’s true- sometimes being a freelance writer can be lonely. You work often on your own. For those people that don’t really want to be around a lot of other people or hear a bunch of background noise, it’s perfect. I’m one of those people- I’m really fine being alone and prefer being able to have control over my working environment.

There are ways to combat being alone so much as a freelance writer, including:

  • Get out once a week to work in a coffee shop
  • Join a coworking space
  • Join a weekly meeting in-person with others
  • Find an online accountability buddy you can Skype with once a week
  • Plan in podcast appearances or calls with clients


Other People Might Not Understand What You Do

Some people will act like you’re not working at all. Even though working from home and solopreneurship are picking up traction all over the world, there are still plenty of people out there who are confused and assume you’re sitting at home watching Netflix all day.

It’s sometimes hard to help family members or friends realize that you’re not available all hours of the day. There’s a fine balance between being able to meet a friend for lunch and having someone get angry that you didn’t answer their text message while you were working on a client project.

There’s no perfect solution to this- you may, in fact, have to get more serious with laying down boundaries for everyone in your world to understand when and how you’ll be able to respond to them. Sometimes all it takes are a few gentle reminders, but in other situations, you might have to put your foot down.


You Will Deal with Bad Clients

While it should always be a goal to work only with ideal clients in your business, that’s not always possible. You usually have to go through a couple of bad experience before you settle on the right people to work with.

When you have a bad client, there are a few things I recommend you do to make this situation easier:

  • Recognize what role, if any, you played in this process
  • End the relationship as soon as and as professionally as possible
  • Move on and look to find a better client to fill that space
  • Apply any lessons learned to your hunt for new clients

In many cases, there are red flags that we see early on with some bad clients that can help us refine the process of finding better clients in the future.


Your Income Will Fluctuate

I encourage you to think of this one like a game. It’s not always possible to predict your income perfectly as a freelance writer, but there are steps you can take to guard against the famine part of the feast and famine cycle.

Here are my tips for handling a fluctuating income:

  • Focus on netting a particular dollar amount of projects or retainers every single month
  • Have an action plan to get freelance writing cash fast when you need it
  • Make sure you always have money saved in case of an emergency


You Will Type a Lot

It goes without saying that you’ll be at the keyboard quite a bit as a freelance writer, right? This can lead to some painful issues, including eye strain and carpal tunnel. Do your best to take breaks often. Consider getting a standing desk to minimize the pain of sitting all the time.

Take breaks for ten minutes every hour to get a break from typing. I use peppermint oil on my wrists to eradicate the pain from typing too much and I find it’s really helpful.

Regular breaks and knowing your own limits will help you tremendously as you prepare for a career as a freelance writer.


What are the downsides you’ve had to learn how to navigate as a freelancer?