Is Freelancing Easy?

freelancing-easyFreelancing 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 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. 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 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?”

Share your thoughts in the comments.


  1. says

    No freelancing is definitely not easier than having a regular job.
    But it’s worth every effort. I feel much less as a “slave” than before.

    With freelancing you do have “more bosses”, but you can simply end working for one, if he doesn’t treat you right.

    I love it :)

  2. says

    Easy? I wish. I enjoy freelancing but it is never every easy. I’ve had demanding full-time staff jobs that were much much easier than drumming up work every single day. Oh, and paid twice as much.

    I regularly warn would-be freelancers to set aside a LOT of money before they even start.

  3. says

    Hi Gregor,

    You are so right. There are definitely advantages to freelancing and choosing your own “bosses” is one of them. The perks are part of what make the hard work worth it.

    Hi Caitlin,

    So true. Freelancing is definitely demanding. I also believe it’s important to start out with a lot of savings–especially if freelancing will be your only income.

  4. Angela Walters says

    Working from home for me is like working in an office. It’s just that you don’t need wake up early to dress up, catch the train or spend hours commuting. Working from home requires discipline. There are jobs that you can work on flexible hours but there are work that requires you to be online for a specific hours. I have been working from home for for quite some time and I can say that it requires a lot of discipline to remain focus of your tasks. You also need to have a dedicated time for work to be able to meet your deadlines and a consistent communication with your boss or other team members.

  5. says

    It’s so true. Multiple bosses since we work on multiple projects and lots of different personalities! As were heading into the Holidays I’m asking myself can I really afford to take a couple days off? No pay and I’ll get behind. Good article, thanks for sharing.

  6. says

    It’s feels really nice that many other people are feeling the same thing like I do. I’ve had enough with people looking down on me and told me that I’m wasting my potential by being a freelancer, that I should get a “real job”.
    Definitely going to share this great post.

  7. Rob Hayes says

    Not much to add. This sums it up pretty good.

    Freelancing ain’t easy; no benefits or time off is tough. But you get rewarded in other ways.

    Nice post, and good to see a site for us lone guns :)

    • Ryan Domm-Thomas says

      Thanks for the read, Rob! Like you said, the rewards aren’t those like paid time off but we are rewarded in so many other ways!

      Keep checking back and keep letting us know what you think!

  8. says

    Taxes – hate em. Crap work, no pay. And, “Always something to do.” is funny … so true.

    A sense of being “on top of your work” is great and I’ve developed ways to do this, simply, but not fully. Perhaps a blog on”how to stay on top of your work” would be good.

    Happy New Year Laura.

  9. says

    Anyone that says it is easy has not done it!

    When I went into it I thought it will be great, and it is but much much harder than I thought. You have to use skills you never wanted to develop or think about. I hate sales but love what I do. As a freelancer I have to fight through those sales tasks to keep going.

  10. says

    I hate having to handle taxes – with a passion!

    Regarding sales. I don’t like selling at all. One way to make it easier to sell is to go after clients similar to ones you’ve had in the past. They tend to be easier sells.

    Nice points up above Laura. And why is it that there’s an endless supply of things to do? Crazy how that works.

  11. says

    Hi, interesting post.

    What also could make freelancing hard is having a mindset that works against you. Especially starting freelancers whom having start building a track record can think and feel inadequate. Like you mention in #5 you will have to know how to sell your service.

    I worked sales most of my work life and it’s not easy. Reading news to stay current in your industry, taking new training to continue to sharpen your skills, on top of doing all the activities involved in marketing/selling/delivering your service.

    What really makes it hard is the shifting of the thinking and behaviors to being your own business owner. Most cases employee thinking creeps up and makes it hard.

    Thanks for sharing your insights.


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