5 Things Every True Freelancer Hates About Freelancing

Freedom, but at what cost!?

Jenny Medeiros
5 min readMar 25, 2018
Photo by Tim Gouw on Unsplash

Yes, freelancing is great. You get to set your own hours, decide where your office is going to be, give yourself a raise, and fire annoying clients.

Sounds swell. However, there are a few choice things about freelancing and digital nomadism that can make the office cubicle seem not so bad after all.

If you’re a freelancer, the upcoming rant will have you nodding in agreement. If you’re not a freelancer but you’re seriously thinking about becoming one, allow me to present what freelancing is really like before you make the leap.

Your schedule can be pure and utter chaos

When you work in an office, you start at 9 am and you finish at 5 pm. Done. You get to drop whatever you’re doing and prance off home. That doesn’t happen when you’re a freelancer.

Sometimes you don’t start working until 2 pm. Other days you wake up early but discover you really should clean your kitchen today. Then after you’re done literally vacuuming the ceiling, you sit down at your desk only to tumble down a social media rabbit hole for the next four hours.

Case in point:

An actual post I wrote in a freelance Facebook group about a day that happens all too often.

It happens.

Unless you’re a master at self-discipline, being the boss of your own schedule tempts you to get a little too liberal with it. Some days are wildly productive, others are just impossible. It almost makes you miss the neat and tidy structure of a 9 - 5 job. (Almost.)

Clients. Just…clients

Anyone who has to hunt for their own clients knows the pains of dealing with them on the daily. You even begin to recognize the different breeds:

  • The lost soul who doesn’t quite know what they want.
  • The good-natured startup founder who needs everything done for cheap.
  • The mysterious employer who takes forever to respond, and when they do, it’s to ask for 152 edits.
  • And, of course, the charming gremlin who goes up in smoke and doesn’t pay you at all.

You also get used to seeing elaborate job postings asking for complex, time-consuming work with requirements like these:

So generous.

Oh, and you get rejected. A lot.

In all honesty, sometimes the hassle of dealing with clients makes you miss just getting work handed down to you by someone else. Although after you sift through the cheapskates and scammers, you do find some pretty decent people who make it all worthwhile.

No designated work space

There are days when you love the fact that you get to choose where your office is going to be for the day, but some days it’s just plain inconvenient.

For digital nomads, your desk is wherever you can sit down. This means lugging around all your work supplies until you can awkwardly balance your laptop on your lap or nab a clean table at a café.

No desk plant or quirky mug for you.

People think you don’t have a “real” job

Apparently, when you say you’re a freelancer who works from home you can get hit by some interesting responses like, “Since you’re home, could you look after my dog this Wednesday?” or, “Wow! So it’s like a permanent holiday then? So lucky!”

No. Just no. It’s still a job that we need to do to pay our bills. We have client calls, we have deadlines, we need to get sh*t done. Plus, most of us can’t even focus when another person is breathing in the same room, let alone when someone else’s kids or pets are flapping around.

Work. Is. Work.

Rolling your eyes at bad freelancing ads

Since you’re probably Googling a lot of “freelancer-y” things, your browser does that creepy thing where it shows you related ads. Enter the hoard of free online courses, webinars, and once-in-a-lifetime master classes.

But once in a while, you’ll see ads like these which just make you snort at how hilariously unrealistic they are:

An ad that popped up on my Tumblr

Okay. Okay. Let’s get one thing straight: no self-respecting freelancer works like that. No-one is working on a beach. There’s sand, there’s water, sun glaring down on the screen — stuff that can literally ruin your laptop.

Carol in the photo there (let’s call her Carol) is an idiot who should be on the sand sipping piña coladas with her friends. Not on the most uncomfortable-looking rock with a laptop dangerously balanced on her sweaty lap so she can get some good ol’ work done.

“Hey, Tom. Yes, we’re having our conference call about my upcoming deadline next to a very loud ocean. What’s that? I can’t hear you over the billion screaming children on the beach. No, that wasn’t me shrieking it was a seagull. Hello? I think my connection is failing. Tom?”

Yeah, no. Not happening.

So, why be a freelancer?

While there are countless things we freelancers can moan and gripe about, the fact remains that none of us would truly return to the office. There is one major reason why: Freedom.

Even if we have to work in a cramped café with slow Wi-Fi, we get to make that choice (and we can also choose to switch cafés). If we have a bad client, we get to tell them where they can shove their low-paying project (but maybe don’t do that). If we have a horrible work-life balance, we can take three “self-care” days in a row and try again on Monday. It’s all about choice.

Freelancing can definitely suck, but it can also be pretty rewarding too.

Are you a freelancer? What’s your major pet peeve?



Jenny Medeiros

Tech writer/editor who dreams of living in a sustainable house with a delightfully stupid cat.