Why Freelance Is Bad: The Perils Of Working For Yourself

We’re big fans of freelance work here at NomadTalk, we’d have to be really – I’ve been freelancing for nearly 20 years now but, at the same time, we have to acknowledge that freelance work has its downsides.

In fact, we’ve identified at least 20 reasons why freelance is bad and you might to want to consider doing something else instead. Of course, we hope that you won’t, but we do hope that it will make you think a little harder about how you decide to go freelance.

The Top 20 Reasons Why Freelance Is Bad (And What To Do About It)


Don’t get too distressed… you can overcome all of these issues with a bit of thought but it’s worth thinking about them before you get started.

Reason One – The Pay Sucks


It doesn’t have to suck but many freelancers find that it does. This is because they’ve not spent enough time working out how much to charge and because they think that they’re going to get all their business on sites like Upwork.

You have to know what you’re worth and know where to find clients to avoid getting paid badly.

Reason Two – There Are Very Few Benefits


I won’t say “no benefits” because my freelance career has provided me with several free vacations (back when I wrote about travel, mainly) and the occasional free course or book.

But that’s about it and you can’t pay your rent in free courses or vacations. You are responsible for your own insurance, overhead, and equipment and you need to build that into what you charge.

Reason Three – It’s A Sales Job


Unless you seriously intend to depend on “winning work” from job sites for the rest of your life (and that’s a really bad plan) then you’re going to need to learn to sell and, in our experience, many would-be freelancers would rather die.

If you can’t find clients and close their business; you’d be better off staying as an employee. You’re never going to live the life of your dreams.

Reason Four – It Needs Experience


Sure, you can find freelance work if you have no experience, heck we’re even putting a guide together on how to do this but it won’t be very well-paid and worse, it’s not likely to help you develop the kind of experience you need to get paid more.

A stint in real-world employment is always the best idea if you want to make a career out of freelance work. Not only do you get relevant experience, but you get to learn what clients really care about (hint: it’s making or saving money).

Reason Five – It’s Harder Than A “Real Job”


Oh, the sad looks of disappointment when freelancers finally realize that they traded in a desk job they thought was hard for a really hard job.

Sure, you can set your own hours and wear what you like but you also need to do sales, marketing, accounting, administration, etc. and that means you’re going to work much harder as a freelancer than as a corporate lackey. That is until you can afford to pay somebody else to do them for you – then you can be a boss and work harder too.

Reason Six – You Need Business Savvy


A freelancer is a businessperson as much as they are a graphic designer, writer or coder (or whatever). That means you can’t get away with winging it for very long, sooner or later you have to learn to run a business.

That’s going to add a lot of pressure in the first few years when you were hoping to be doing 20 hour weeks from Thailand.

Reason Seven – It Takes Self-Discipline


Yup, when you freelance the buck stops with you. You can’t blame the idiot in your team for failing to deliver on time or for sending out substandard product. It’s all on you, all of the time.

That means you need to show up every day and work your behind off to deliver the best you can, all of the time. Work is work and a freelancer without self-discipline is doomed from the get-go. You can’t fake this, you either have it or you starve.

Reason Eight – You Need To Love Your Work


Taking a job you hate for pay is never much fun but at least when you’re working for someone else – they’re taking care of the hassle around that job you hate. They cover benefits, they find the work, they handle taxes, etc.

Nobody ought to be working themselves harder than they have ever worked to do a job they loathe. It’s a recipe for mental burnout and for severe depression. Freelancers need to love their work (or at the very least, they need to like it).

Reason 9 – The Hours Are Terrible


Yeah, you can set your own hours as long as those hours are “all of the time”. Most freelancers aren’t working 9 – 5 or Tim Ferris’ magical 4-hour workweek. They’re slogging for 12-16 hours a day because that’s what it takes to build a successful business and they’re doing that for 6 or even 7 days a week too.

Sadly, this is how the world works and I’ve found that it’s rare for anyone freelancing as a digital nomad to end up with a long-term secure client list. It’s a genuine disadvantage not being able to network with clients and meet with them face-to-face. You’re always going to be selling and marketing.

Reason 10 – It’s Hard To Find Your Own Space


Work from home and sooner or later your personal and private life bleed into one. Work from cafes and co-working spaces, though, and you rarely end up with a space to call your own. It’s a massive drag having to build your own little office every day in those places.

I try to combat this by renting apartments with at least one bedroom and working out of a separate room from where I sleep. I don’t always get this right, mind  you, but we move on after a month if there’s nowhere to work.

Reason 11 – Clients Don’t Grow On Trees


If you’ve never freelanced before then your biggest problem is “where do I find clients?”  This may remain the problem for years to come too.

This is why we strongly encourage you to build a freelance practice while you have a job. It gives you time to plan how to approach clients and to see if you can succeed at it.

Reason 12 – You Have To Deal With People


Introverts, beware. This is not a job for people who hate dealing with other people. Not only do you have to sell to them, but you also have to support them. You have to deal with suppliers, the taxman, the accounting people, etc. too.

Freelancers may not spend as much time in long boring meetings as corporate employees do but let’s be fair about this; the job’s not absent from human interaction either.

Reason 13 – You Have To Be Tough


Wait until the first time that you complete a massive project which has taken weeks of work to find out that the client’s absconded with your work and your planned “massive payday” is now under severe threat, then you’ll understand how tough you need to be.

You’re going to have to read the client the riot act and get your money at the same time. Ideally, you don’t want to destroy the relationship and have them bad-mouthing you all over town but at the same time, you have to get paid. This stuff is hardcore.

Reason 14 – You Have To Be Able To Project Manage


You are responsible for each project that you take on from beginning to end. You can’t dump it on a project management team and wait for them to parcel it up – you’ve got to work out each step in the process and define who has to do what and when.

You also need to communicate this stuff well to the client or they’re going to start losing patience with you rapidly.

If you’ve never managed a project before, then buy a book on project management and learn fast.

Reason 15 – You’re Going To Be Alone, A Lot


I don’t mind this, but I know other freelancers that can’t bear their own company. They’re usually the ones hanging around co-working spaces like a bad smell desperately trying to start conversations with people who just want to work.

They’re why I always have headphones in if I am forced to use a co-working space.

You need to get used to your own company. It can be challenging at first but after a while, you can come to love it. This is the true joy of being your own boss – no sounds of stupid while you work.

Reason 16 – It’s Easy To Become A Workaholic


It’s your business and every success is your own. This may be the most addictive feeling on Earth. The trouble is that if you keep chasing the high, you’re going to end up working all the hours that there are.

This, in turn, is going to lead to burnout. You have to make time for yourself in freelance life. Set aside one day a week or a few hours a day for things that aren’t work and stick to that. I almost never work Sundays because I know how unpleasant burnout can be from personal experience.

Reason 17 – You Still Have To Be Visibly Professional


I find it strange how many freelancers I know add all their clients to their Facebook and then start boasting about their drunken exploits. This is a really good way to ensure that work starts drying up.

You need to keep space between your personal and professional life and in your professional life, you ought to keep things professional. That’s why LinkedIn exists. Add people to your network there not on Facebook.

Wear smart business dress to meetings. That kind of thing. Be visibly professional.

Reason 18 – No Paid Vacations


Yeah, when you work for yourself – there are no paid vacations ever again. If you’re not working, you’re not earning, it’s that simple.

Worse, it’s hard to find time for vacations when you have a nice bank of clients who all have weekly orders…

The good news is that if you get your pricing right, you can afford unpaid vacations, eventually.

Reason 19 – You’ve Got To Master Time Management


You can’t be sloppy with your timekeeping when you work for yourself. People judge you for being late in real life. Clients aren’t going to put up with it for a minute.

You have to manage your time effectively on every project and every job. Your biggest reputational boost will come from meeting deadlines. It’s the most important aspect of the job.

Reason 20 – Everyone Else Thinks You’ve Not Got A Real Job


This gets to be really frustrating. Because you don’t have an office, everyone assumes you’re playing at work rather than really working.

There’s not much you can do about this except clear boundaries with the people around you and if they don’t adhere to them – find somewhere else to work from.



So, there you have it 20 drawbacks to freelance work. Of course, we think the benefits outweigh the negatives and love working as freelance writers but it’s also not for everyone.

Nicholas Barang

Nicholas Barang is a veteran digital nomad. In fact, he was probably "digital nomading" before it was called that. He believes that anyone can make a free and independent life if they want to. He wants to help those who commit to finding their own path. And to cut through the nonsense told about this "lifestyle" by those in search of a quick buck. If you want to reach him you can send him an e-mail to nick at nomadtalk.net. You can learn more about him here - About Us

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