10 Honest Reasons Why Freelancing Sucks (And My Thoughts on How to Deal With Them)

Photo by Isaac Benhesed on Unsplash

“But surely it’s better than a 9–5?”

Yes, absolutely! But just know that there are times when freelancing sucks, too.

Before you get swept away with visions of working on the beach, do your research.

Know what you’re getting into.

If you’re thinking about diving into the world of freelancing then I think it’s important that you know about some of the downsides of this style of lifestyle too — it’s important to manage expectations.

I wrote this article so that you can successfully navigate your freelance career from the start and learn some honest reasons why freelancing isn’t always as it makes out to be.

“Don’t expect things to happen. It’s better to be surprised than to be disappointed.”

Reasons Why Freelancing (Sometimes) Sucks

Here are 10 reasons why freelancing sometimes sucks, written from my own personal experience:

1. It can be lonely

Freelancing for most of us means working from home. Without the face-to-face interactions of the daily office, it can sometimes feel a little lonely doing this all the time.

Who wants to talk about last night’s episode?!

Personally I think it’s even more important for freelancers to engage in their community in which they live to be able to interaction socially with other human beings.

This means more interactions outside of work.

Whether this is via volunteering, clubs or social events, you’ll need to make an extra effort when you work for yourself.

Make sure to also jump on the phone where possible, to get the same interaction with clients that you would otherwise do through meetings. It’ll really help build up a rapport, too.

Also, I think it’s important to go for coffee every now and again if you work from home, to allow a proper break from your work environment.

2. It’s much harder to separate work from personal life

Most freelancers, especially relatively new ones, will be using the same laptop to answer work emails as they do to check their facebook.

This is bad in 2 ways:

  • It allows for so many distractions
  • It’s hard to switch off from work

My phone is my work and personal phone, and my computer is the same. In fact, the same room where I do most of my work is the same room where I eat my breakfast.

I’m contactable by clients pretty much all the time.

Even when your work day is done, it can be hard to not feel guilty for not working too, because you don’t have that break in environment and you probably still have the same devices in your hands. [If this sounds like you, take a read of this.]

Photo by rawpixel.com on Unsplash

3. You start to see everything as a money making opportunity

I’ve started to do this recently with some of my hobbies.

For example, one of my hobbies is photography.

I’ve often wondered if I should try turning this into a little side-gig but have yet to actually pursue anything.

I think there’s a danger to want to turn every hobby into a money-making opportunity. We need to remember to have activities that fully allow us to create and experience joy, without the pressure of work.

Otherwise our whole lives will be centred around money.

4. Finding clients is a pain in the bum

And clients can drop you at any time.

It takes some skill to be able to detect good and bad clients. I’ve written a few notes on what to look out for here on Medium.

Make yourself a great asset and the clients will keep coming back to you.

And if you’re lucky enough to find a new client, read this -> 5 ways to impress a new client.

5. You’re still working for someone else

Remember, freelancing is still just working for someone else, so keep this in mind before you quit your 9–5!

I’m working on starting my own business as well as working part-time for a variety of clients in a bid to escape this.

I love the mix of both freelancing and entrepreneurship and feel like the two compliment each other well.

For now!

6. The hours can sometimes be long and inconvenient

In my bid to impress clients (particularly when they’re new), I sometimes spend time working when really I shouldn’t be. Whether this is working an extra long day to deliver a project quickly, or working after-hours to try and hook a new lead, know that your hours won’t always allow for a glorious ‘flexible’ working lifestyle.

I also work across several different European and American time zones which can lead to a few headaches.

Strong communication is key to ensure you keep control of your hours.

Be sure to articulate to clients when you are reachable and when you are not. Let them know if you’re taking time off.

“Surfer on a sandy beach beneath a flock of birds during sunset in San Diego” by frank mckenna on Unsplash

7. No work equals no pay

I always used to get such a weird sense of satisfaction during my old job when I would be sitting on a beach on vacation while getting a paycheque delivered into my account!

It’s one of the perks of a salary that you just won’t get as a freelancer.

When working for yourself, an hour worked is an hour earned, so bear that in mind when taking time off.

8. Freelancing isn’t scalable

At some point, you’ll realize that freelancing isn’t really scalable. Sure, you can charge more for your time but there’s always going to be a limited number of billable hours in any given week.

If you’re happy with this, that’s great!

If not, it may be a good idea to think about passive sources of income, or starting your own business.

9. Your only support is yourself

Sadly there’s no IT or HR hotline when it comes to freelancing.

If something goes wrong with your invoice billing system or your internet dies, it’s your problem.

If a relationship with a client sours, it’s on you to address it.

And if something like your laptop breaks, know that it will have to come out of your own pocket to fix it.

10. There are more frequent difficult conversations to be had

Negotiating pay, discussing scope creep and conducting interviews are all unpleasant conversations.

And the bad news is that they are more frequent when freelancing because you have to do it with every single client, rather than just one employer!

The good news is that it definitely gets easier with time, and you’ll begin to learn methods to deal with these tricky conversations or to avoid them happening altogether.


Have I scared you off?!

I hope not! It’s not my intention to scare you away from freelancing.

In fact, I love freelancing and I highly recommend trying it!

Hopefully you’ll be able to learn a thing or two from the above 10 points.

Most of all, I hope I can help manage expectations.

While freelancing is certainly great, there are not many articles that talk about the ugly side of freelancing so I wanted to give you just a little bit of guidance from what I’ve learned since I’ve started.

In the future I also hope to write a similar article about why I love freelancing, but in the meantime… let me know if you have any questions!