The top 10 challenges freelancers face and how you can overcome them

Independence.  Working to your own schedule.  A chance to be your own boss.

The positives that come with being a freelancer have been extolled in many blogs and by many professionals who are currently freelancing. No doubt those positive influenced your own decision to quit your full-time job and go freelance.

What we often forget about are the issues that can also present themselves to freelancers that those in a full-time role do not experience.

Caunce O’Hara & Co Ltd have 25 years of experience providing protection to freelancers through business insurance. We’ve collated what we feel are the top 10 challenges that freelancers face along with some solutions to help overcome them and thrive in your freelance career.

1) Jack of all trades. Master of…?

As a freelancer you need to be talented at just about everything. Finance, writing, marketing, technology and sales are part your everyday activities. It can be fun, and you can learn a lot of new skills in a very short time, but it can also be extremely challenging trying to cover all of these tasks by yourself.

With each task fighting with the others for priority, to the point where they all become a priority, you have to become very disciplined and organised very quickly, so you don’t lose the plot.

A good way of dealing with this is to set a day or two aside each week to cover your tasks. This will help prevent your other work being disrupted and will allow you to complete the ‘housework’ that keeps your freelancing efforts in motion.

2) Meeting unrealistic demands

Not every client will be sensible when it comes to what they demand of you. This is especially the case if you are only just entering the world of freelance and are not experienced at managing client expectations.

To manage expectations, it is important you set clear outlines of what you can and cannot do for your client and ensure your client agrees to those terms. If your client then asks you to step outside of what you have agreed, you can simply refer to these outlines and point out that it is out of your realm of expertise or beyond your client’s budget.

There will be times when not meeting a client’s demands could be perceived as not fulfilling your end of an agreement. This could lead to your client taking legal action against you. For this situation, it is always important to have comprehensive insurance in place to support you in the event of this occurring.

3) Ensuring you are paid on time

You deliver your project and are happy that your client’s brief is met in full. You may even feel a little proud of the work you have produced. Then comes the dreaded task of asking for payment.

Asking a client for payment can be very awkward, especially if you are relatively inexperienced. Many freelancers send out invoices and move on to the next project expecting payment to come in on time. But business is unpredictable at the best of times, and your client’s viewpoint might differ to your own regarding the work you have delivered for them, to the point where your client isn’t willing to pay you what you agreed.

Or in more common cases your client has their own payment schedule which they rigidly stick to. This can mean the payment you were expecting to receive within 7 days may not materialise until 60 days, or more, after your invoice is received.

Late payments are a scourge of the freelance community. An estimated £2.5 billion is lost every year from the UK economy as a result. Late payments and non-payments also cause the end of many freelance careers and small businesses every year. 

How do I approach this?

A direct approach is needed to ensure you are paid. A reminder email sent out a few days prior to the due date or even a late payment charge can be great ways to encourage your clients not to miss a payment date.

It is important to have a written agreement of agreed payment terms on hand that you can refer back to if a client denies agreeing to pay for your services or tries to pay you a reduced amount. This can be in the form of a client contract, but even an email can count as a form of written agreement in case this situation arises.

4) It’s a battle to win new business

Every project, task and client you ever win as a freelancer will have been hard-earned as part of a constant bidding war. You will find yourself battling with two or three other freelancers for every project. This can be an exhausting way to live, but necessary if you want to be successful.

The best way to beat the competition is to make yourself stand out. This is easier said than done and is advice you’ll have heard many times and even passed on to your peers.

Get your value proposition right

In the digital age it’s important to build a great online presence for your freelance business. If you market it well, you may find clients are drawn to you with their enquiries. What is key to your marketing is to identify exactly what your value proposition is. No amount of marketing and advertising will bring you the business you desire if you don’t know what it is you offer that makes you different.

Once you’ve generated the opportunity to quote for a project, ensure you create quality proposals to stand out from your competition. These will make you look professional and instil trust in your client that you will do a great job for them.

Wherever possible, try to avoid websites that require you to bid for work, these usually require lots of time commitment and effort for very little reward. The percentage of jobs you win from these platforms is likely to be quite low too.

5) Everyone thinks you’re unemployed

As a freelancer do you ever get that feeling that your friends and family don’t take you seriously? Questions from your family and friends like, when will you get a ‘real’ job? crop up regularly in conversation.

You’re making money and paying the bills. You’re sorting your own taxes and generally making your own decisions. Yet not getting up for a daily commute, and not wearing a shirt and tie, seem to be key indicators that you’re not an employed professional.

Challenges like this that involve changing the perceptions of those around you can be difficult to overcome. Perseverance and working hard will help, and as your freelancing efforts flourish and your enterprise grows people will start to realise that you are very much a valued part of the workforce.

You’ll simply have to put up with the jokes until then!

6) It can a be lonely career

Freelancers spend a lot of time in their own company, it’s the nature of the job, with many working from their kitchen table or spare room. Self-employed people have mentioned in recent surveys they have felt lonely since becoming their own boss.

The effects of loneliness can be far reaching and have an adverse effect on your health, your family and your work.

Reach out and meet new people

The rise of relatively inexpensive co-working spaces in cities and towns across the country has provided many opportunities for freelancers to work in spaces surrounded by like-minded professionals. Co-working spaces also provide opportunities to potentially collaborate with other freelancers on various projects. It all starts by introducing yourself with a smile.

There are also plenty of networking opportunities to choose from. Some are free to attend, some ask for a nominal attendance fee, while others are membership based and charge an annual subscription. These events are a great opportunity to regularly meet people, providing you with the chance to make connections and win new business.

Networking may seem daunting at first, and it will take you out of your comfort zone, but it can open a lot of doors to new opportunities for your business. You will also grow in confidence in how you promote yourself and your value proposition to clients.

7) Procrastination

This can pose a major problem for your freelancing efforts unless you are organised. There are a few things you can do to stay motivated, including keeping a checklist and a timetable of your projects to help you focus on your deadlines. Both will help you allocate your time to different tasks, just in different formats.

Timetables are good for you as they give you start and end points to work to and they help ensure that you get your projects completed on time. Checklists can be reduced into tasks on a granular basis. For example, if you are copywriting for a website you could list each individual webpage to be checked-off when completed.

8) Long hours

Escaping the daily 9 to 5 won’t necessarily mean you will enjoy easier working hours or more comfortable working conditions or more agreeable working relationships.

If you’re not careful, you could find yourself working longer hours as a freelancer than you ever did as an employee. Try and remember that the only person who can tell you to stop working is you.

Longer hours can mean more work done, which can result in more money invoiced each month. However, promising every client that you’ll prioritise their project can be dangerous. It’s easy to burnout if you continually work long hours. You could also find yourself so uptight and rushed that you make mistakes and don’t produce the high quality of work you and your clients are aiming for.

So, how do you solve the problem of knowing when to stop?

Sticking to set working hours is often the only way to ensure you don’t wear yourself down too quickly. This takes self-control, but it is important to maintain a healthy lifestyle.

If you know you will need to work Late or start earlier than you would like, then try to ensure you take breaks throughout the day to take your mind off your work.

You could go for a run, walk to the shops, read a book or simply go out and water your garden. Making a conscious move to take a rest from your work can free you from ‘work mode’ and help make your working hours more manageable.

9) Micromanagement

There will be times when you almost feel more like a personal assistant to your clients rather than a freelancer.

Constant updates and long emails can be time-consuming to deal with and you’ll feel you need to do this to keep your clients happy.

To solve this issue, you will need to learn to politely say ‘No’

  • Politely inform your client the work is not complete yet and you will update them when it is.
  • Keep phone conversations short when possible – try usingdedicated business phone system for the same.
  • Reply to long emails with short, but firm statements that you don’t have the time right now, but you will address the various points when you can devote the time needed to do so.

This links back to Point 2, managing your client’s expectations. It can be difficult and awkward at first, but once you do it for the first time you can do it over again.

10) Varied workload

Feast or famine is a reality of freelancing, but it doesn’t have to be this way. Instead of wasting your spare time during your ‘famine’ cycle, spend that time looking for new clients and marketing your services.

Simple things such as posting on LinkedIn about being available for project work can help and could land you a new client.

Your life as a freelancer will have its ups and downs. Understanding this prepares you to meet these challenges head on and take advantage of them.

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Caunce O'Hara

Caunce O'Hara are experts for freelancer & contractor professional indemnity and liability business insurance, legal expenses cover & IR35 contract reviews.