Working as a Freelancer Easy or a Myth?

Freelancing may be a more common career choice than it used to be, but there are still people who don’t get it. It’s still not uncommon to hear the following sentiment:

“How hard could it be?”

The uninformed acquaintance who uttered those words was talking about the work of a freelance web designer, but as a freelancer myself, I was a bit offended by his comment. Still, I know that there are others who feel the same way about freelancers.

With all of the recent media coverage on freelancing, it’s hard to believe that there are still those who don’t consider freelancing to be a “real job.”

In this post, I describe seven of the difficult challenges that freelancers face. If you have a client or acquaintance who doesn’t understand that freelancing involves actual work, direct them to this post.

If you liked this post, you may also like Why You Don’t Really Have Eight Billable Hours Each Day.

7 Challenges that Make Freelancing Hard

If it’s done right, freelancing is hard work. Freelancers who claim otherwise probably won’t stay in business long.

That’s not to say that freelancing isn’t rewarding, because it is.

Here are some of the challenges that make freelancing harder than many people realize:

  1. Freelance work is not a play. The uninformed and inexperienced often picture a freelancer who spends their time working on easy, fun projects. This misperception stems from the fact that freelancers have the ability to turn work down (when they can afford it). The truth is that many freelancing projects are not easy and fun. Those who hire freelancers typically do the easy and fun projects themselves. Clients typically assign their most difficult projects to their freelancer–either because they don’t know how to do the project or don’t want to do it.
  2. Multiple bosses. Another common misperception about freelancing is that the freelancer has no boss. While technically this is true, it does not mean that the freelancer doesn’t answer to anyone. Freelancers have to answer to their clients. And, in order to get enough work, most freelancers work on projects for multiple clients at the same time. So, instead of seeming like there is no boss, freelancers often feel like they are working for multiple bosses at the same time. If you think one boss is hard to please, imagine working for five bosses.
  3. Feast or famine cycle. Getting regular pay is another freelancing challenge. Most non-freelancers are used to receiving a steady income. For the freelancer, things are different. One month they may have more work than they can handle (and a higher income as a result). The very next month the freelancer may have hardly anything to do (and bring in very little income). Of course, there are methods for freelancers to manage the feast or famine cycle, but those methods aren’t foolproof.
  4. No work, no pay. Most employers provide their employees with paid vacation and sick days. Freelancers, however, get no paid days off. If a freelancer doesn’t work one day, the freelancer receives no pay for that day off. As a result, freelancers often drag work along on their vacations or work even when they don’t feel well. (I’ve found the lack of paid days off is one of the hardest concepts to explain to non-freelancers.)
  5. Sales. Do you like to sell things? Me either. In fact, for a lot of us, sales is one of our least favorite things to do. However, if you want to stay in business as a freelancer, you’ll learn to sell if you’re going to succeed. You see, each time a potential client contacts you they have to be sold on why your services are what they need and why they need to pay you what you ask. It is true that Freelancers can manage their sales invoices online easily using tools like, but generating sales invoices themselves is a task. The constant selling surprises many new freelancers. It’s also something that even seasoned freelancers struggle with.
  6. Always something to do. When you’re a freelancer, there’s always something you need to be doing. Your work is never really done. Even if you’re going through a slow period, there are things you should do. You probably need to update your portfolio or your freelancing blog. Or you should be strengthening your social media profiles. Of course, you can always do the accounting and administrative tasks that go along with running any small business.
  7. More complicated taxes. Last, but not least, are the accounting issues that go along with freelancing. Not only do you need to keep excellent records of all income received and all business expenses, but a freelancer’s taxes are usually more complicated. If you are a sole proprietor in the United States, you will need to fill out a Schedule C for your tax return. You will probably need to pay taxes quarterly. Plus, you will pay higher taxes due to the self-employment tax.

So, the next time someone tells you that freelancing is easy, or claims that you aren’t really working–show them this post.

Your Turn In your opinion, is freelancing easier or harder than other jobs? What do you tell people who think you don’t have a “real job?”

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