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The Cons of Freelancing

I am a mother, writer, and freelancer who understands the ups and downs of freelance work.

What are the downsides of freelancing?

What are the downsides of freelancing?

The Downsides of Full-Time Freelancing

Freelancing and the gig economy are more popular than ever before. It is dubbed the new economy. While I have worked in the gig economy for over 10 years now as a freelancer, I am slightly saddened by the idea of that. I am a freelancer because there are a lot of pros. I work my own hours, which is important because I have a chronic illness.

Without freelancing, I probably wouldn't be able to work at all. It feeds my family and pays my bills; what more could I ask for? But there are some serious cons to being a freelancer, and knowing what they are can help you plan for your future and make freelancing your full-time reality if the pros outweigh the cons for you. For me, they do, but let's not pretend freelancing is without its flaws. Nothing is.

Health Insurance

This is by far the hardest part of freelancing for me. With chronic illness, it's a whole lot harder to take care of when insurance for myself is over $1000 monthly for a high-deductible plan on the open marketplace. While this might not be such a big deal for some people, those of us with pre-existing conditions or who are older may have trouble satisfying our health care needs in a cost-saving way. Basically, when you don't have a company matching how much you pay in insurance, it gets ridiculous.

If you make under $60,000 or so, you can apply for subsidized health care, and for many, that might be the best option. I have chosen a different approach of having a high-deductible health insurance that I don't really use. It's more there for emergencies, and I pay cash for most of my medical needs. You can actually save 40% or more just by paying cash, so that's what I do. If you are thinking of going into freelancing full-time, you have to figure out your health insurance.

Unsteady Income

While I am lucky in the fact that I have multiple clients that I have had for many years with steady work, sometimes clients take vacations and won't put in an order for a month. Sometimes they want to take a break. The idea that any part of my work is steady, even in my position, is a fairy tale.

I can usually get enough orders to keep myself busy with several weeks booked ahead, there was a month and a half at the beginning of this year that I didn't get one order, and I was scrambling to find new clients for new work. This meant paying a higher freelancing fee, as well as having a definite dip in my income. It also meant I branched out and picked up a new client that I've had ever since, and I really like the projects offered.

The way to combat an unsteady income is to have a healthy savings. This can be hard in the beginning when you start freelancing, and you're not making as much as you will six months down the road with experience and references on your profile. Before you make freelancing your full-time gig, I would suggest having three to six months put back for the lean times. They will come, so you're better off preparing for them.

Freelancing Fees

If you go through one of only a few freelancing sites to pick up work, you will become very intimately familiar with fees. Basically, every dollar I make through a freelancing site is paid a fee as a percentage of my work. This percentage can go from 5% to 20%. Every dollar I make, Upwork gets a piece of it. Since I have not found a way to get around these fees without breaking the terms of service, I have tried to make sure that most of the work I do falls under the 5% category instead of the 20%.

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The platform I use most to find clients is Upwork, formerly Odesk. Their fee system works differently, and it's changed through the years, but now all of my new clients, up to the first $500, I have to pay a 20% fee for. For older clients that I have done $500 to $10,000 in business with, I have to pay 10% freelance platform fee. I try to keep long-term clients that will do over $10,000 in business with me. After that $10,000 mark, all money made after that is a 5% fee. Three-quarters of my clientele are in that category.

I am very choosy about taking on a new client because I know that a fifth of the money I make in the beginning is going to go to the platform. Find clients that need work for years, not weeks and months, because you will save yourself a tremendous amount of money in fees, to the tune of 15% of your monthly income.


Once you become a full-time self-employed freelancer, your tax situation is going to change. You will no longer be able to use the easy tax forms; you will have to either get them done yourself, use a more expensive tax program for self-employed, or you are going to have to learn a lot about the tax code.

It's not so simple with self-employed, there are fewer taxes taken out, you can expense the fees that we just talked about, as well as your home office, equipment, Internet. There is a lot more to tax time when you're self-employed. You might want to brush up on some of the rules or do like I do and pay an extra $80 every year for the more expensive self-employed TurboTax forms. However you do it, taxes will be more complicated.

You Can't Be Unproductive . . . Ever

One of the biggest differences between freelancing and having a regular job is that you only get paid if you're productive. You don't really get to have a bad day where you don't get a lot done because if you don't get it done, you don't get paid.

I'm a writer. I write novels for publishers, and I don't get paid until the book is delivered. This means there is no paid time; there is no option for me just to pretend I'm working to get through the day and not get yelled at by my bosses. I've had plenty of jobs, and there were always those days when not a whole lot got done. If I have one of those days now, I just don't get paid.

To make this con a pro, you really need to work on time management and efficiency. As deadlines loomed and work wasn't finished, I learned quickly what my actual capacity is. I work better under pressure. I break down my day using block scheduling and usually work three to four hours a day for full-time pay. I would never have gotten this efficient if it wasn't a requirement of freelancing. You will be amazed at how productive you can be when you have to be because you need to pay rent.

Last Thoughts

I probably will never have a regular job again. I've been my own boss for so long that I doubt I would want to. I know that, of course, I would if I had to if the orders dried up and I couldn't find something else, but I never want to again.

Even with all of the cons above, I will always prefer freelancing to the alternative. The freedom and the ability to take the jobs I want to take surpass the stability that can sometimes come with a steady job. Maybe a regular job is not stability, but the sense of stability in having that check come every Friday. I know that I have to make that check happen; I have to find the clients, manage my time, get the job done, and do a good job so that they will keep ordering from me.

It's a lot, it's not as easy, but I really wouldn't have it any other way. I wish I would have been more prepared for freelancing and the lifestyle that it can create, but I would never go back. I don't think that I could at this point. Every con can be managed; you just have to find your way.

This content is accurate and true to the best of the author’s knowledge and is not meant to substitute for formal and individualized advice from a qualified professional.

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