6 Tough Realities about Being a Freelancer (And How to Deal With Them)

by Tom Ewer 5 Minutes

Long roadIf you’re new to freelancing or considering it as a career option, you may see the road ahead as strewn with roses. You’ll have the best boss in the world (you)! Your time will be your own!

Unfortunately, like most roses, freelance life has its thorny side and there are issues you will soon find you have to cope with. Freelancing is hard work! Six of the hidden pitfalls are outlined below, along with strategies to help you cope and make a success of your new or proposed business.

1. The Dream Is Not What It Seems

There you are, in the very early days of having left full-time employment, striking out on your own full of hope. And why not? You have a whole new career ahead of you! It’s exciting stuff, and your head may well be full of dreams. Now, you can finally do things your way! No one can tell you what to do, or how to do it!

The problem is, the person who now has to do that is you, and this means coming down to earth with a bump. You need the discipline to work long hours to succeed. Building a young freelance business can be hard, work characterized by irregular hours, a struggle to get and keep clients, and money issues.

But remember: you’re in this for a reason. Yes, you are working hard, clients are not easy to come by, and they need to be treated well – but you have a vision of where you want to be and the commitment to make it happen. All you need to do is adjust your dream to accommodate reality.

2. Underselling Yourself Is All Too Easy

One of the greatest temptations for a new freelancer is to undersell their talent. People do this because they’re unsure they can get what they believe they’re worth, or because they have no idea what they’re actually worth.

This is a bad idea because it can be a vicious circle – if you don’t believe you will get paid what you’re worth, clients will be very happy to take advantage.

Counter this temptation fast by doing some basic calculations. Work out what you need to earn to survive each month (including items like utility bills, child care, and sundries like printer ink and pens), how many hours you are hoping to work, and divide the money by the hours. The result is how much you need to earn per hour to get by – anything you can get on top is ‘profit’.

Research what others in your field are being paid; sometimes trade body websites or business forums will provide that sort of data, and trade unions can also be helpful. You can also ask in a relevant forum on a site like LinkedIn – it does no harm to try!

If you find others are being paid much more or much less than your estimated hourly rate, you’ve probably got your sums wrong. If they’re getting a lot more, do they have a lot more experience? You may have a cost advantage, if you’re sure of your figures. If they’re getting a lot less, either you will need to find a way to control your expenses, or you’ll need to work a lot more hours to survive.

3. Defining Your Skillset Is a Struggle

Sometimes it seems like your competitors have all sorts of wonderful accomplishments they boast of in their CVs and on their websites, but you can’t think of anything to say that will rival their accomplishments. Particularly when you’re starting out, it can be daunting to see the claims others make and hard to draw up your own list.

A skillset is simply that existing knowledge and expertise that you bring with you, from every source. To define it, you need to leverage everything you have done to maximize your value – if you have existing relevant experience, make sure you let potential clients know.

Think laterally. Perhaps you’ve organized a charity event or planned a regular meeting? Even managing kids involves skills such as organization and calmness under pressure. Maybe you’re particularly honest, passionate about your subject, or organized? Are you a natural leader, or a particularly good team member?

You need to search deeply through all your past experiences and put together a set of positive messages about your skills, framed to generalize about your strengths based on particular examples.

4. Burnout Is a Real Danger

The day may come when you wake up and find you are fresh out of ideas. Your mind is a blank slate, your energy has gone and your problems seem insurmountable. It’s a state of mental, emotional and physical exhaustion caused by stress – and freelance life can be stressful.

If you think you’re in danger of burning out, recognize these danger signs and find ways to manage the stress that’s causing your problems.

To back away from burnout, you need to take control. If you’re working too much, you have to carve out some downtime. Learn relaxation techniques such as meditation or yoga, or even fly-tying or writing poetry. Do things that take your mind completely away from your problems.

5. Work Can Dry Up Unexpectedly

Everyone has bad patches; they happen to the best and most talented of people, for various reasons. Sometimes it’s something as ‘macro’ as the national economy – people aren’t spending money, which filters down to you. Sometimes it’s more personal things, like ill health in the family or major clients being bought out or going under.

Ideally you need to be preparing for when work tapers off before it does. Always have irons in the fire – make sure you keep a high profile in forums and social media where your clients are likely to see you, and keep a regular check on employment websites for your sector. Network in your specialist area – attend exhibitions and conferences if funds permit.

6. Things Are Darkest Before the Dawn

Though the list of issues above sounds grim, none of them need to be overwhelming. With determination, you can make the realities work for you rather than against you.

Yes, you will hit points where you simply feel like throwing in the towel; when everything seems to be piling up against you and you can’t see a way forward. But these often happen just before the dawn.

There are many benefits to freelance life that help outweigh the possible negatives. You do have far more freedom and flexibility with your work, and with courage, commitment, organization and a little bit of ingenuity, you can find yourself in the happy situation of having the lifestyle, career and income you were dreaming of.


Let’s recap. To succeed as a freelancer you need to

  1. Avoid disenchantment by holding on to your vision.
  2. Avoid underselling yourself by working out what you need to earn to survive, and researching what your competitors make.
  3. Avoid skillset blanks by leveraging all your strengths.
  4. Avoid burnout by taking breaks and reconnecting with your favourite pastimes.
  5. Cope with dry spells of work through preparation – network, raise your profile, and keep in touch with job opportunities.
  6. Remember, you will get through the grimmer realities and achieve the many great benefits of freelancing!

Use the advice above to make the foundation for a long, enjoyable freelancing career. Do you have any thoughts on other pitfalls, or helpful advice? Let us know in the comments below!

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by Tom Ewer
Tom Ewer and the WordCandy team have clocked some serious mileage as freelancers, agency employees and even agency owners over the years, and they love sharing their combined expertise here on the Bidsketch blog.