Join us for a 30-min Timely Tour

The unglamorous side of freelancing

Last updated on 
January 3, 2020

Check out:

When it comes to misunderstood jobs, freelancing is up there at the top. People have grand ideas about a life of leisure and flexibility: wake up when you want, choose projects that excite you, work from your local coffee shop (or from your sofa, or your bed), and never have to deal with office politics or annoying bosses again.

But alas – in spite of its multiple perks, there are also many pitfalls to freelancing… yet most people don’t know about these until they’ve taken the leap. To save future souls from crippling freelance shock, we’ve made a big list detailing the unglamorous side of freelancing everyone should know about.


One of the worst things about freelancing is the lingering fear that you will never work again. A day late delivering that big job? The client will ditch you, and you’ll never work again. Struggled a bit with that last project? The client will ditch you, and you’ll never work again. Even if you spend far more time than you ever did before working (and to be honest, you probably will), it will usually be imbued with the stubborn, infuriating fear that you will never work again. Accept it and embrace it – that’s just how it is.

Inability to switch off

One of the best things about permanent jobs (apart from the stability of that monthly paycheck) is the separation between work and life. Your weekends are your own; so are your evenings. You leave the office and that’s it: work-time has finished, and play-time can begin. Not so for freelancers. Just packed up for the evening? Guaranteed, that’s when that ‘URGENT!!!’ email will arrive from a client across the globe – meaning you have to get off the sofa, reopen your laptop and get back to work. Trying to ignore it doesn’t work, either, because no matter how hard you try, that email will be all you can think about.


To succeed at freelancing you need to be self-motivated and be able to self-manage. Some days you might be good at this, but others are a different story. It’s scarily easy to lose hours going down a Wikipedia rabbit hole, or watching other people’s Instagram stories, convinced everyone is not only far more successful than you, but also happier and less stressed, too. Then there are the days where it’s cold and dark, but your bed is warm and cosy and inviting. Are you strong enough to get out of it?

Getting paid

Doing your work on time and sending an invoice on time doesn’t guarantee being paid on time. Most freelancers have experienced clients who are late at paying – or worse, clients who won’t pay at all. How you navigate this is another source of freelancing worry: you don’t want to be too pushy in case it’s an honest oversight – but how long do you wait before becoming more forceful? If your last three requests for payment went unanswered, do you unleash the threat of legal action? Is this an empty threat? Do you have the money to even take legal action? Should you just cut your losses and let it go? Can you afford to do that? It’s a never-ending cycle of worry.

Difficult client relationships

Clients – can’t live with them, can’t live without them. To be fair, some clients are a dream to work with. Others, not so much. Whether it’s clients who seem to think you should do limitless revisions for no extra pay, to those clients who give you maddeningly vague briefs (e.g. “I don’t really know what I want… But I’ll know when I see it, so can just you have a play around and send me some examples?”), dealing with bad clients is par for the course for freelancing.

Taking holidays

As we’ve established, switching off is hard for freelancers, but taking a holiday is even harder. It’s not that you don’t have the finances to go – it’s more that you’re too afraid of spending them, lest you never work again. Even if you do decide to take that break, putting your work life on hold can be impossible. You might get a last-minute, super-urgent request from a prospective new client; can you afford to turn down the work – or more importantly, the chance to impress a potentially long-term, lucrative client?

Staying on top of your taxes

Just the thought of tax is enough to make people baulk, but for freelancers, thinking about taxes is a necessary evil. Whereas those in permanent employment enjoy the luxury of having their tax deducted, as a freelancer you need to do this yourself – or else pay for an accountant to do it for you. Thinking about which things you can potentially expense, or wondering whether you should be saving all your receipts is a common way of procrastinating for many freelancers.


There are times where it’s normal to spend days not really speaking to another human being. When your workload is piling up and deadlines are approaching, sometimes you just have to hold your nose and plough through it – and that often means not having any work-life balance until you’re done. In spite of how glad you might be to have left the office behind you, these are the times you’ll find yourself reminiscing about how you used to chat to other people while making coffee, or enjoying post-work Friday beers with the co-workers you actually liked.


The nature of freelance seems to be one of two things: A) You have so much work that it’s all you can think about, and you have to decline every single invitation going because “deadlines”, or; B) You have little to no work, so you worry about making rent, worry about accepting invitations (can you even afford to go out?), and of course, worry that you’ll never work again. The feast vs famine nature of freelancing will never go away, no matter how good you are. It’s just the nature of the job.

Uninspiring projects

The freelancing dream was to work on projects that truly excited you – but the reality is sometimes very different. Depending on whether you’re in the feast or famine cycle, you probably will end up doing jobs you don’t like. You can’t always afford to be picky, and if a job request comes up that’s mind-numbingly tedious but well-paid, are you really going to turn it down? No matter how much you try to stick to your principles, that nagging fear will start up again – you’ll never work again! – and before you know it, you’ve not only agreed to the job, you’ve asked for more work, too.

Considering going freelance?

Take a peek at our our resources on how to know if freelancing is for you and how to become successful as a freelancer.

Keep your team ticking

Timely automatically tracks team hours,
activity and capacity to keep remote work visible.
Lead happier, healthier teams.

Book a demo

Keep your team ticking

Timely automatically tracks team hours, activity
and capacity to keep everyone connected.
Lead happier, healthier teams.

Book a demo

Related articles

Read also

No items found.

Related articles

No items found.
Designed by vikings in Oslo, Norway