The Tiresome Side of Freelance Writing

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There are many aspects to freelance writing, and to be honest it can have its tiresome side. This is not a rant (okay, maybe a little), and I hope you will find some useful nuggets of information in today’s post.

When you first started freelancing, what was it that excited you the most?

For me, it was living my dream. Working from home or wherever. Writing for a living. Being able to travel while working.

But it’s not always all sugar and spice. In fact, there were — are — some things that are necessary but annoying.

Here’s a question: What did you find most unpleasantly surprising?

These are the things I consider necessary (but can be annoyingly annoying).

Image by Ag Ku from Pixabay

There’s having to deal with your own paperwork.

That means:

  1. Taxes

When I had an office job, I didn’t have to worry about computing my taxes and filing them. HR did all that for me. Ever since I went freelance full-time…whew! Good thing I have an accountant friend who helps me with this.

  1. Health Insurance 

Another thing that my previous day jobs included was health insurance. I didn’t realize how much I would miss this benefit until I got seriously ill and spent two weeks in the hospital without insurance. Lesson learned. I got a private health insurance policy but boy, my bank account is NOT happy at all.

  1. Life Insurance

Yep – insurance is tiresome. You think you’re okay without it then something happens. That’s why I want to revise that “death and taxes” idiom to “death, taxes, and insurance”. Especially if you want to make sure your family is taken care of if something happens to you. It’s not easy to find a policy with good coverage and reasonable requirements, but if you can find life insurance without a medical exam, you might want to grab it. It’s even more pressing these days.

Then there’s setting up a workspace at home that is 200% conducive to working and free from distraction. This is relatively easy for people who live alone, but for those with families, it is a whole different story. I’ve said it before, and I will say it again — freelance writers who have children, I salute you! I do not know how you make it work.

If you have a dedicated office, then you’re lucky. Whether you have one or not, you will likely need to get a desk and/or an office chair, which do not come cheap. Working at the dining table, on the sofa, or in bed will get the job done, but only to a certain extent. Plus, it’s not good for your health — physical and otherwise.

This brings us to another not-so-good aspect of freelance writing. Self-discipline.

This topic has been beaten to death, but based on my experience, it still cannot be emphasized enough. Many office workers have had a taste of the work-from-home setup because of the pandemic, but they have the “luxury” of a supervisor to whom they are accountable. Consciously or not, this has a positive effect in terms of getting work done.

For freelance writers who are their own boss, this could be a little tricky. It is true that we can set our own work schedule and work whenever we want. The thing is, as any freelancer with a little experience would know, that work whenever thing doesn’t always work out the way we want.

If you are not self-disciplined or organized enough, it is very likely that you would hear that sound Douglas Adams described in his famous quote.

[bctt tweet=”I love deadlines. I love the whooshing noise they make as they go by. -Douglas Adams” username=”freelancewj”]

So, yes, freelancing has its perks, but you do need a minimum level of self-discipline and organization to keep clients. This is a whole new discussion altogether, but here is a quick tip: Create your daily schedule (I use Google Calendar) and stick to it. What is written in the calendar is executed. Of course, there will be times when you need to make adjustments. That’s where the beauty of being the boss of your time comes in.

How about you? Are you new to freelance writing? What difficulties have you faced so far?

I’d also love to hear from the more experienced of you. Maybe you can help our fellow freelancers who are new to this.

Sound off in the comments!

Also read: Worker’s Compensation for the Freelance Writing Business: The Rights and the Risks

If you need more help with freelancing, browse our Resources for Writers section.



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2 responses
  1. LB Perkins Avatar

    Mini-rant in response: I think Slack is idiotic, but that’s just my own tender little tech hatred. I don’t have as much of a problem with some of your annoyances (hear, hear on the taxes, though!) but I do have some items to add to the most annoying aspects of freelancing (which I have done, on and off, for 25 years)
    1. Invoicing: Even with the automation of Excel, double checking every digit and cross-referencing the project number and the invoice number is exhausting to me. Smells of math.
    2. Chasing payment: I have mostly wonderful clients, but I have found that the higher the pay rate, the slower the check. Net 60 is NOT ok. Ever.

  2. Faith Avatar

    Yes, I agree! And as someone who moves location all the time, it can be hard to find enough free time. I am also a caretaker for a handicapped person, so their needs aren’t on a schedule. The self-discipline to make time in a constantly changing schedule and environment has not been easy for me. xD

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