The Biggest Sources of Stress for the Self Employed According to Real Freelancers

The size of self employed workforce is increasing fast. Statistics from January 2017 show that the UK has 4.8 million self employed workers, accounting for 15% of the entire UK labour force. This is set to continue growing as attitudes to work and employment continue to shift. 

Being self employed has its perks. You don’t directly answer to bosses. You can work from anywhere you like. You can choose which work to take on. You have full control of your working day and how you carry out tasks.

For many, this is a great setup. However, being a freelancer isn’t smooth sailing all the time. Your income isn’t necessarily guaranteed. You have less job security when compared to traditional employment.

Ultimately, whether the business succeeds or fails rests solely on one person. That’s a lot of weight for a single pair of shoulders to carry. This is one of the main problems of self employment: It can be extremely stressful.

In fact, research in 2017 has shown that 1 in 5 self employed households suffer from stress, mainly around money worries.

People have cited that financial worries are one of the biggest barriers that stops them from making the leap into the world of self employment in the first place.

It seems like self employment and money related stress go hand in hand.

Whilst money worries are undoubtedly one of the biggest sources of stress for the self employed, there are other factors, too. 

Self employed stress: Income and finances

The truth is that when you are self employed, there will be times when you worry about money. It’s unavoidable. As a business of one, you will be painfully aware of how much money you are owed, as well as any money you may owe.

From the freelancers that I spoke to, money concerns seemed to stem from finding enough clients, being paid on time, and avoiding illness or situations that render you unable to work.

Self employed people don’t get statutory holiday pay and sick pay, which can often lead to freelancers pressing on with work when, in reality, it would be much healthier to take a step back to recuperate or relax (this can lead to a whole host of other stress issues, too).

Late payment is a big issue for freelancers. It can cause havoc with your cash flow. This is particularly unfair when freelancers have kept to their side of the bargain by providing work that is on time and up to standard, yet have to wait months to be financially reimbursed for it.

Check out some of the responses I received on Twitter in regards to freelancers and late payment:

Self employed stress: Taxes

Being self employed means you are 100% responsible for your own tax affairs. You have to register with HMRC. You then have to make sure all of your taxes are filed and paid on time.

Paying taxes and keeping up with bookkeeping are two of the many tasks that freelancers have to take responsibility for. They’re really important jobs. If errors are made, it could result in financial penalties, which could spell disaster for any self employed businesses. In the same vein, it could also mean that too much tax is paid, which can also result in unnecessary financial hardship.

Whilst there are helpful resources out there, some freelancers have mentioned that they find this information difficult to access and digest. On top of this, the accounts side of the business may not be something a freelancer is immediately savvy with.

Whilst it is possible to file your own tax returns, many self employed people choose to hire accountants. This is a wise move if you’re not confident processing your own numbers, especially if your business is complex.

Self employed stress: Finding leads and clients

When some people enter self employment, they have a plan. They already have a network of contacts and can easily pick up work. For others, this isn’t the case.

If your client base is thin on the ground, it can be really worrying. It can mean your profits drop. This can lead to money worries. It can also be extremely demotivating.

For many people, leads are earned as a result of hard graft - building up their reputation - and getting their name out there.

However, the initial task of finding and winning clients in the first place causes a great amount of stress for freelancers. Marketing is just another job on a seemingly endless list of tasks that freelancers must keep up with in order to stay afloat.

Also, if marketing isn’t a freelancer’s forte, it can be tricky to learn the ropes of an unrelated discipline. This can make finding clients even more difficult, intensifying the stress caused.

It should also be noted that the hunt for new work isn’t just a one off thing; it’s a core part of freelance life and is a continuous grind for many self employed people.

Self employed stress: The uncertainty

The feeling of the unknown is another point that freelancers raised as a pressure point. Due to the nature of freelance work, very few people have a solid safety net to fall back on should things take a turn for the worse.

A key client may be lost, or perhaps an injury or illness could put someone out of work for a period of time. It could just be that demand for the freelancer’s services slows down, leaving them with lots of unbooked time.

This is what people have described as ‘the feast or famine’ nature of freelancing. Sometimes, it’s simply not possible to predict how much work will come in month to month.

Not knowing how much work, and therefore how much money, will be coming in month to month can be unnerving. It can also make planning and living your life outside of work more difficult, as highlighted by Helen’s tweet below:

Self employed stress: Confidence and motivation

This point of stress can be seen as an amalgamation of other previously mentioned factors.

If you are failing to land clients or are struggling to consistently pull in your target earnings, this can really knock your confidence. It can force you to ask whether you really should be doing what you’re doing, throwing you into a self-doubt fuelled stupor.

It can be really tricky to pull yourself out of. Freelancing isn’t the normal career path for most of society and it’s not really something you’re taught to do. Whilst freelancers may have the help and support of friends and family, this isn’t really the same as the formalised structure and support network that comes with full time employment.

On top of this, contact hours with other experienced professionals can dip, which makes it more difficult to get feedback and validation on any ideas, both of which are important for keeping up morale and confidence.

What the freelancers said

Fabio Virgi, Maia Marketing

As a newly-launched marketing & web design business, one of the key stress points is finding new clients. When you're working in a saturated space like this, it can quickly become intimidating and easy to start self-doubting, knocking your own confidence and questioning whether you're on the right track.


What has helped me is actually quite simple, and not enough people do it in my opinion: get yourself out there and actually connect with other local businesses. I've begun doing that over the last few weeks and I'm pleasantly surprised at just how many business owners are open to collaborating with others.


I also run a couple of blogs, LetsTalk-Tech.com and FabMeetsWorld.com, and I've been trying to turn them into a business for a while now. Again, the key to my successes so far has been picking up the phone and connecting with people! Sitting back and hoping for companies to hand you money isn't going to happen, so I've forced myself to think creatively about how I can help them generate a buzz around their products -- and monetise my hard work in the process.

Tom Bourlet, Take It Offline

What I have found the most frustrating is the intense expectations and time-demanding of small companies. The expectations of a small company paying for 8 hours work per month is virtually the same as a big company paying for 50 hours per month.

The reality is if a small company doesn’t have enough budget, then you can’t implement everything you would like in the limited amount of time you have with their account. They will however expect the world and also require instant results and instantaneous ROI.



Matt Goolding, KYO Digital Marketing Collective

Personally, one of the biggest stresses is the lack of clarity about whether a new client will pay their invoice on time, or at all. Wherever possible it's critical to get a contract in place, and it's even better to get a percentage of payment made before embarking on a new project.

Ideally, set the precedent of full payment prior to conducting your work. It's stressful to know that you could stumble across an invoice-shy client at any time, and it's true that freelancers are vulnerable to the worst offenders.



Beth Kennedy, Freelance Copywriter

Payment in general: I bet you will get this one from every freelancer. I'm admittedly very very insistent and maybe even a little pushy with payment - because a lot of my previous clients would take months to pay or even wouldn't pay at all.

It's kind of like when you're a teacher in the classroom and one of the naughty kids plays up so you say "Right, thanks to the naughty kid, EVERYONE has to stay behind after class." The non-payers ruined it for the clients who do pay.



Rachel Carrell, Koru Kids

I'm the CEO of a tech company, Koru Kids, which arranges childcare for working parents. My team and I hear every day from parents who are working as freelancers or in the 'gig' economy - often in media or the creative industries - and really struggling to figure out how childcare fits into their lives. Often a mum (it's almost always the mum, very rarely the dad) has taken leave of a year or so to look after a baby, and then finds themselves stuck when it's time to get back into work.

The problem is that most childcare needs to be planned many months in advance, such as nurseries which can have waiting lists of 6-12 months or even more. Parents working freelance therefore find themselves in a Catch-22: they can't commit to new projects because they haven't got childcare sorted, but they can't get childcare sorted because they don't know if they're going to have a solid income.

I've spoken to many parents who have committed to the costs but then find they don't actually have work yet when the time comes, so they end up looking after their children while paying the childcare costs for no reason.

Nursery and other forms of childcare are too expensive to gamble with, with many nurseries costing up to £2000 per month for full time care. A nanny is even more expensive at over £3000 or more, and even a nanny share - which can be much more cost effective - can clock in at £1800 per month. Unless you have a huge buffer of savings (and remember, these are parents who have just taken time off work and also faced the additional many expenses of a baby, so they're unlikely to have much in the way of savings!), it's very very difficult to get back into work in these circumstances.



Luke Hughes, Origym Personal Trainer Courses

A big stress is continuously having to justify and sell my capabilities to a business owner or company. Due to a lack of quality in fitness tutoring, many owners are very skeptical on the quality they receive, hence I always have to go through a very laborious process of justifying my abilities to gain trust and confidence of the employer for just a small contracted amount of work. This becomes particularly stressful and tedious due to the continuous nature.



Tracey Dickerson, PR by NorthStar

You never stop feeling guilty as you could always be doing more. Whilst it's great to have the freedom to manage your own time, servicing clients is just one very small piece of the pie. You have to find time for networking, SEO, new business pitches, website maintenance, accounts, outsourcing, business strategy, training, PR, marketing, IT, blogging, social media, public speaking - the list goes on.



Isabelle, Freelance Copywriter

Being massively screwed over by both the accountant and HMRC. Tax is definitely a big worry - there's a lot of mixed messages, a lot of bad accountants who talk nonsense and rinse small businesses...

Before I had a limited company I didn't need an accountant and all was a lot easier, but I can't do business without now.



Helen Anglin, Freelance Content Marketing at Exposure Ninja

The biggest stress as a freelancer is not knowing how much work you’ll receive each month. The concern of not being able to pay rent and bills is a worry that all freelancers have been through at some point. While most of us are lucky to have consistency, there are always times when clients suddenly can’t pay or need to stop work. Not being able to afford the basics such as food and bills can cause a lot of panic.



Chris Groves, Freelance Editor at Exposure Ninja + Freelance Sports Journalist

The freedom of working as a freelancer can often be the main cause of stress, as well as a reliever of it. Whilst the concept of jumping from job to job, task to task, without a corporate structure or overhanging management, may seem inviting, it puts extra pressure on you to self-motivate and remain consistent.

Freelancing is not the system of work we are wired to prepare for during education, so you are somewhat on your own when you get started. Having a limited number of people to turn to for advice or assistance can leave you stressed, especially early on. If you can handle that stress and learn from it, though, the personal rewards go far beyond your income.



Saima Omar, S.O Content Marketing

Clients who have unrealistic expectations are stressful. They want the world and they want it right now. You pull in all your effort and resources to deliver the work and then they are not happy with the press release/newsletter/blog because they weren't sure of what they wanted in the first place or had not provided a brief! In other words, clients who are struggling due to lack of resource from their own side bring stress in my freelance world.



Col Skinner, Digital Marketing Consultant at Profoundry

I started this business with a firm belief that I can create a relatively stress-free working life. This meant I don’t take on too much work at any one time. I don’t take on clients that are clearly going to stress me out. I don’t stretch myself by trying to be a jack of all trades. With this in mind, I must admit I don’t actually get very stressed these days.

If I had to choose one thing, the biggest source of stress has to be the constant hunt for new work. This won’t be the case for many freelancers who find one or two retained clients and then are sorted for years to come. But for me, as a growing business and with clients that use me on a flexible basis, the hunt is real.

Some people cannot hack this feast and famine nature of freelancing but I thrive on the thrill of the chase and having lots of new potential clients / opportunities each month that could turn into my next collaborative partnership. I think you either embrace the challenge and approach it strategically or else it eats you alive.



Lena Kay, Transformation Coach, Speaker, and Trainer

As an entrepreneur and a coach who works with many other entrepreneurs and start ups - one of the biggest sources of stress is the time to fit everything in. You focus on one area of your business - another area gets neglected. And some smart alec will say "just outsource". Well many times people don't have the finance or budget for outsourcing.

Most entrepreneurs are everything in their business: the accountant, the sales consultant, the marketer, the content writer, video editor, photographer, the deliverer of the service, the cleaner - everything!

As you can imagine it's easy to go into overwhelm and sometimes the immense amount of work in front of you will paralyse you from any action. The emotional ups and downs have their toll on you. You need to develop emotional resilience or you will lose big time.

This leads many people to lack of confidence and procrastination. Amazing experts I have come across - great at what they do but poor at the business stuff. I have found that the best way I deal with this is by creating systems. I focus on each area of my business and I plan a month, a week and then a day in advance when I will do what. I also have a 6 month and 12 month plan.

Managing time and emotions is a huge deal as a business owner. I have made peace with the fact that I never will get it all done. I do what I can. I work 16 hour days a lot, but I fit in time for eating well, meditating, exercise and reading. Ultimately it is about enjoying the journey on the way to the destination.



Sarah Key, Freelance Marketing Communications

One of my biggest stresses is the uncertainty. There's usually a nagging concern in the back of my mind that I don't know what will happen and how much work I will have in a month's time.

The next most prominent concern for me is where to turn for support with business questions, processes or policy. A few months in, I realised I might need terms and conditions but didn't know how to draft them or who to get expertise from. Similarly, friends have struggled with financial matters, website questions and IT issues.



Dane Cobain, Freelance Author

I think the biggest source of stress for me is the fact that there's always something else to do. I try my best to manage my time but it takes a lot of adjustment. I'm only just going into my second month of full-time freelancing, and it's taken me this long to settle down to just working 9-6.

Because I was moonlighting for months before, I got into this habit of just working as much as I possibly could. This continued into my first month of full-time freelancing, and I kept accepting every job I got offered and working evenings and weekends.

I realised I was working way harder - and earning much more - than I needed to, and so I'm trying to scale back. But it isn't easy, especially with clients in different time zones sending messages at different times. It's difficult to say no and to set expectations, and I'm generally stressed at all times whether I'm working or not because I can never be sure that I'll hit my deadlines.



Closing thoughts: is the stress worth it?

This is a long blog post, with people opening up and giving their honest opinion on the most stressful elements of their self employed careers.

Many of the freelancers I spoke to indicated in their emails that they were only giving the negatives because that’s all I had asked for. For many, the positives far outweigh the negatives.

In reality, stress impacts people in different ways. The triggers of stress will differ from person to person. However, it’s interesting that across most of the freelancers that I spoke to, the overarching theme, whether directly or indirectly, involved money and income.

Essentially, we are at the mercy of our clients. Our cash flow depends on them paying invoices on time, or even finding the work in the first place.

There are times when freelancing feels like a grind - but you take the good and the bad, the highs and the lows together. They’re antagonistic. They reinforce each other. Together, they create a complete picture of what it’s actually like to be a freelancer.

A big thank you to all of the freelancers I spoke to who offered their insights.

About Zack Neary-Hayes


A headshot of Zack Neary-Hayes, a freelance SEO and digital marketer

Zack is a freelance SEO and digital marketer currently based in Leeds. He's a fan of remote working and also reckons he's a dab hand in the kitchen. He's not a fan of writing about himself in the third person. 

Follow Zack on Twitter and connect on LinkedIn.

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