In the Age of the Digital Nomad, What Are the Pros and Cons of Being a Freelancer?

Kicking back in the sun, beach to your left, pina colada to your right and laptop straight ahead. Globetrotting the world with your best friend Mr Internet and life’s your oyster.

Is it really possible? Yes, for sure. Is it like this all the time? Hell, no! Anyone that tries to sell you the idea that freelancing as a digital nomad is always easy is telling porkies. But, despite it not being quite like the dream you imagine it could be, there are a lot of lifestyle benefits. If like me, you value your freedom and want to do things your own way – freelancing could be the way forward.

If it’s your ambition to freelance or you’re thinking about taking the jump, this article is for you.

What the hell do I know about being a freelancer?

For three years I’ve been a freelance writer and content consultant after leaving a full-time role in London. Before freelancing I enjoyed my career developing and executing content strategies for established businesses and startups.

It’s something I was good at, celebrating some significant successes during that time (including building an online guide to London that often outranked Time Out magazine). Such is the world, significant life events don’t always fit smoothly alongside career trajectories. Soon realised I would have to go it alone earlier than I’d hoped.

Although I’ve always wanted to be able to work independently and remotely – when I had to take this jump I didn’t quite feel ready. How would I find clients? What should I charge for my services? What services should I provide? WILL ANYONE EVEN WANT TO HIRE ME?!? Luckily I figured all of that out, and here I am now!

Cons of being a freelancer

I’m going to end with the positives so stick with me, but first, get ready for some straight-up facts.

You still have to answer to other people

If you want to freelance because you don’t have to answer to anyone, good luck with that… As a freelancer, you usually survive by taking on clients. You need to answer to each and every one of these clients instead of just one boss.

Although your clients are looking for your expertise, they may have a very specific idea of what they want. Regular updates, taking feedback and accurately recording your hours is important to ensure your work meets or exceeds what you promised.

If you let people down, word will get around. Possibly resulting in losing out on long term clients AND referrals.

Say hello to the working holiday

All of that globe-trotting might sound great – and mostly it is. But, if you’re not getting holiday pay, it can be tempting (or you may need) to work whilst your away.

That may not sound too bad but, don’t underestimate how difficult it can be to motivate yourself to answer emails and sit in long meetings when everyone else is hanging out at the beach.

Also, your Internet or phone signal doesn’t always work. There are plenty of places where I’ve stayed where the connection is terrible to non-existant and had to kiss goodbye to my working plans.

Either you work like crazy before you leave to ensure you’re on top of everything. Making sure clients know well in advance you won’t be avaialble at short notice and planning ahead with them. Or, you could find a way to schedule anything you can’t do beforehand for times that are convenient for you. Ensuring that wherever your staying has enough connectivity for your needs.

You don’t get sick pay

We all get sick sometimes, so it’s inevitable that there will be days when you’re too ill to work.

It is possible to pay for income insurance that will cover you if you’re unable to work due to illness or accident. I can’t recommend any as I’ve not taken out any policies myself, but you can read more about income insurance policies here. It’s something that many freelancers choose to do to protect themselves.

Separating your working life and home life can be challenging

If you get distracted by dirty dishes in the sink or experimenting with a new living room layout – productivity can drop dramatically. Your home isn’t your office, and your office shouldn’t be your home, so try and separate the two in a way that works for you.

Making sure I can relax at home but concentrate at work has been really important. This is definitely possible to do successfully, but it requires some self-discipline and being honest with yourself!

You could also think about renting an office space… see below!

It can be lonely

Don’t underestimate the companionship and inspiration you get from working alongside likeminded people. If you’re creative or an extrovert, it can be lonely working on your own. You naturally sometimes want to ask for an opinion of what you’re working on or share what’s going on in your day.

To combat lonely freelancer syndrome, I rent desk space at Stranger Collective in Falmouth. It’s a great way of meeting people, as well as injecting sometimes much-needed laughter and vibrancy into a long day of writing! There’s also mostly always a fully stocked biscuit tin, my favourite cheese crackers and tea.

Irregular income makes budgeting hard

Sometimes you might be so busy you have to turn down work, or even take on an intern. Other times, you’ll have so much time on your hands you won’t know what to do with yourself. This is the same for almost any business that relies on an unpredictable client base.

No matter how good you are at prospecting, lulls in business are inevitable. Regular clients you rely on can go out of business, or several potential leads can all dry up at once. This makes budgeting challenging, especially if you have regular bills to pay. I know freelancers that can go from earning over £80,000 a year to under £15,000 the next.

Putting aside money when you’re busy can help with this, so can ensuring you keep in contact with potential clients & practising your prospecting – but there isn’t anything that can completely protect you from a dry spot.

Tax Returns

If you’re self-employed, you need to keep track of your accounts to ensure you can correctly fill in your tax return. This means being more organised, and semi-mastering the spreadsheet.

Remembering to save and organise receipts, as well as keeping track of what you’ve been paid each month really helps.

If you don’t want to or can’t afford to hire an accountant right away or want to do this yourself, there are apps and platforms to help you.

Pros of being a freelancer

If you’re still here, GREAT! It’s a good sign you’ve not been put off yet. Now for the good bits…

Flexible hours

You may not be able to do whatever you want, whenever you want – but you’re a lot closer to freedom not being tied into the same routine every day.

For some people – being obliged to sit down on a chair right in front of your computer for a specific, scheduled amount of hours is almost unbearably frustrating. Freelancing is when when you get to say “stick it to the man”, and work whatever the hell hours you damn well want (well, most of the time).

Shaping your working hours in a way that suits the lifestyle you want to lead can be hugely rewarding. It allows you to fit around your family’s needs, to pursue interests outside of work and often, means you can be spontaneous. Taking your pet to the vets, looking after a sick family member or getting your hair cut doesn’t require you to ask anyone’s permission.

And, if it’s a beautiful day and you’ve got no looming deadlines, you can fold up your laptop and go for a two-hour hike if you want.

Creative freedom

When you’re a lone wolf, you don’t have to shape your creative process to fit a particular business or agency. This is when you get to do things YOUR way. All the experience, talent and knowledge that you’ve accumulated over the years will inform the best working process for you to produce your best work.

Choosing your clients

In a perfect world, we’d all get to choose which business we worked with. Unfortunately, sometimes, cash flow dictates this. If you’re working with an awkward client, but they’re a major source of your monthly income, dropping them might not be an option.

The upside is that there will be times when you’re busier and can be pickier about who you work with.

Unlimited earnings

Once you’ve figured out how to set your rates (a post on this coming soon), your earnings can be unlimited. You’re only limited by how much work you can take on. This means that although you may sometimes earn less than you would in one full-time job, you have the potential to earn a lot more.

If you’re over capacity, you can always employ people other freelancers help. The sky is the limit, you can take your business wherever you want to take it.

Variety of work

Unless you work in a dynamic agency, you may find yourself stuck working with the same types of businesses over and over again if you’re in a full-time job.

As a freelancer, however, you’ll most likely be working on a range of different projects with a variety of businesses. You also have the freedom to collaborate with anyone you want.

No one looking over your shoulder

If you want to shop for bikinis at 3:30pm on ASOS, you can. And you don’t have to feel guilty.

Time to work on your own projects

Taking away the time it takes to commute, coupled with the freedom resulting from organising your own hours – you may find they have more time to work on passion projects. When you’re not at your desk for hours on end, you can feel more energised. It then doesn’t seem like such a chore to sit down with your computer and get creative.

You can raise a family

“I’d have been back in the office by now if I’d been at my old job. Now I can look after my child and work when he naps, and in the evenings for a few hours when he’s in bed”. – My fellow freelancer Krystal told me recently.

As a designer, Krystal was able to freelance from home. Now she’s taking some time off to raise her little boy, without having to rush getting back to daytime office hours.

You can choose where you work

No commute

Does anyone love their morning commute unless they walk cycle to work?


When living in London I had a 1-hour commute there and back to the office. It was cramped, busy and stressful – my least favourite way to start a morning and evening.

After leaving the office, for months I’d wake up at 7 am, and instead of getting ready to run to the station, I’d go for a walk in the fields next to the house with actual tears in my eyes, because I was so overwhelmed with gratitude that I didn’t have to do that any more.

You can wear what you want

As I mostly worked with startups, I could really wear almost whatever I want. I’m taking cut off jean shorts and frilly socks here. NOW though, even if I want to be naked wear my PJ’s I can… and no one will know! (I actually don’t recommend this, but each to their own!)


If I didn’t think there were better pros to being a freelancer then I wouldn’t be one, but it’s not the same for everyone. Although there are some fairly significant cons that would understandably put some people off, if the benefits outweigh these for you personally – that’s the path you should take.

If you’re a freelancer and I’ve missed anything out that’s essential, let me know in the comments!

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