Fear of Freelancing – What’s Stopping You?

"Fear" by WIlderdom from Flickr

Another week, and another person I work with is deciding to ditch the nine-to-five and make their fortune as a freelancer. Which has me thinking. As much as I enjoy the security of a salaried position and the atmosphere of working in an office with other people, there’s a part of me that wouldn’t mind working from home. It’d save on ironing for starters.

And I’m not the only one.

On Twitter, down the pub, on the bus – it seems like everyone I speak to quite fancies jacking in the daily commute and setting their own hours. But very few of them seem to do it. But why? Why aren’t you a freelancer?

If you’re anything like me, it’s fear.

Fear for your Finances

I don’t know if you’ve noticed, but according to every single newspaper, TV station and placard-waving loon is claiming that we’re in the middle of the second Great Depression. Roaming bands of bailiffs are turfing families out of their homes for coming up a few pence short on their mortgages, and nobody seems to have two pence to rub together.

So it’s no wonder that you’re not keen on leaving behind a guaranteed wage for the murky waters of generating your own income. The last thing you want is spending the rest of your career going slowly mad, eating tins of cold beans while writing out drafts on the back of litter.

But it’s not just that loss of a salary that’s a cause for concern.

Fear of Uncertainty

When you’re working for someone else, chances are that they’re providing you with the work. They’re going to all the trouble of sourcing all of the leads (or paying someone to do so), and you’re just providing the service or product. Simple. The stream of business keeps coming, you keep working, the wages keep getting paid.

But when you leave that workplace behind to strike out on your own, suddenly there’s no guarantee that the work is coming in. You’re competing with other, better established companies and freelance copywriters to secure clients, and people like to keep their lead generation secrets close to their chests.

And these fears of not getting enough custom, or enough cash just feed into the third, most terrifying fear of all.

Fear of Failure

Nobody likes to fail.

And when failure carries a financial penalty, the thought of having to break back in to a faltering jobs market, and the stigma of knowing you’re not as good as you thought you are, you can be damn sure that you really aren’t going to enjoy this failure in the slightest.

So you stay where you are, taking your wages, and falling asleep on the bus. Dreaming about working at home in your pants.

How Do You Defeat Your Fears?

I don’t have the solutions to these problems. If I did, I’d spend my days sprawling on my couch, in my underwear, typing away on my laptop. But I’m hoping for a discussion in the comments section below.

So what’s stopping you going freelance? And if you’ve taken that leap, how did you deal with your fears?

Share your stories in the comments section below, or on the PCN forum.

Image from Flickr


22nd June 2012

Andy Nattan

I’m hoping that someone will do an follow-up post to this, answering the questions I’ve laid out. Are you up to the challenge?

22nd June 2012

Richard Hollins


I suspect that a lot of people who go freelance do so because they got made redundant. That’s what happened to me. The beauty of it is that if you’re lucky, the payoff gives you a financial cushion to tide you over until the work starts coming in. You’re already in a world of uncertainty because your job’s just disappeared, so having a go at freelancing doesn’t seem like such a big deal. As for failure, you can do what I did and claim you’re just testing the waters for a few months and if it doesn’t work, you’ll be back in the jobs market. Luckily for me that didn’t happen.

As for how anyone gives up a solid salary to go freelance, I don’t know. You’ve got to be braver than I was. If you’re going to do it, it’s probably better to do it before you have kids and all the extra cost and responsibility that goes along with that.

22nd June 2012

Yvonne Anderson

Hi Andy

I gave up my salaried, fairly safe job to start my own company in 2008. It was triggered by going for a high profile job that I really wanted and coming second. The act of pouring all my creativity and imagination into that process made me realise I couldn’t go back and needed to stretch my wings. I was 52 at the time and that gave it a feeling of now or never. Since then I have had ups and downs, lots of pressure, plenty of weekend working and recently a prevailing anxiety about the recession and reduction in business opportunities. But I don’t regret it one bit. The pay-off is in having control over your own working life. Just knowing you can walk away from something or someone is liberating enough, but more than that is the knowledge you can make things happen – initiate, innovate and imagine something into being.

It gets me out of bed every day anyway!

22nd June 2012

Siobhan Dignan

I went freelance ten years ago. It was scary but I was unhappy in my job and I could see myself still doing the same thing – the commute, watching the clock and complaining to my husband – in ten years time. Once I passed 40, I knew that getting another agency job in a young industry was probably not going to happen. Also I had kids and needed the flexibility. Still I hesitated. Partly the fear of failure, partly because I liked my colleagues. I also did not want to put my childminder out of a job. I found myself wishing for something bad to happen at the office so I would be forced to jump before heads rolled.

It did and I made the leap. By then several colleagues had left for other agencies, so I had a network of potential clients. The first few years were busy and ideal with a family. With the recession it has gotten harder – agencies and clients are more reluctant to hire third parties if they feel they can write it themselves. Unfortunately, there is a general feeling about that anyone can write.

However I do think there is work out there, but it just takes a bit more self promotion and research to find it. Social media, the internet and the global market has to provide more scope. Depending on the market, writers may need to be able to turn their hand to more things.

On balance, the positives are: freedom, flexibility, variety, no office politics or boring meetings. The negatives: missing human contact, chasing for jobs and payment, can’t always see a job through so the finished piece may vary greatly from your original, and anxiety due to financial insecurity and irregular pay. Freelancers may not get the credit, so the creative ego has to be able to handle that.

I’d say go for it if you: are still young enough to get back to regular employment if it doesn’t work out, have a partner who has a decent paying, secure pensionable job and/or no a big mortgage burden, are good at networking and self promotion, and have good discipline outside a structured workplace. As for me, I have been so de-institutionalised, I could never go back to the 9-5.

Yes, it gets me out of bed, but does it get me out of the dressing gown?

22nd June 2012

Nick Green

It’s something I’ve been mulling over for while. And still am to be honest.

I have a nagging feeling that failure hides in the gap between being good at your job, and being good at your job AND being good at business. Closing that gap is the key.

Writing stuff in the relatively secure and stress-free environment of full-time employment is one thing; doing it with the added pressure of finding new clients, managing existing ones, filing accounts, doing marketing etc is, I’m guessing, something else entirely.

Creative people aren’t (and I’m aware I’m generalising a bit here) always that organised and pragmatic. Not many successful businesses are built on seat-of-the-pants whimsy. There’s got to be nous there too, right?

I’ve seen plenty of talented people promoted to management, only to fall flat on their face. They just weren’t equipped to make the move. Good at their jobs? Undoubtedly. Good at management? Sorry, we forgot to ask.

That’s the difference I’m talking about.

So can you do both? Can you learn to be good at business? Or isn’t it even an issue?

22nd June 2012

Sarah Turner

That’s so true Nick. When I went freelance in 2005 I spent the first few months thinking I was a copywriter before it dawned on me I was a marketer, networker, IT consultant, accountant and a new business manager. I think it was Nick Usborne (or it might have been Andy Maslen -sorry Andy) who said ‘you’re not a copywriter, you run a copywriting business. There’s a difference.’

Before anyone goes freelance I’d advise you to have enough money in the bank to cover all your expenses for six months. Unless you have a nice partner who’s willing to stump up your half of the mortgage for a while.

22nd June 2012

Nick Green


Pretty much what I thought. That mindset change seems to be the key .

But despite the obvious challenges and dry-throat inducing moments of chronic self-doubt, I do still feel that I’m moving inexorably towards going solo. It just seems sort of inevitable.

Maybe it’s an unavoidable by-product of a creative mind. That desire to do stuff on your own terms; to be innovative, curious and keen to set your brain free. Maybe creativity just doesn’t lend itself well to the 9-5, toe the line, do what you’re told corporate-ness of being employed.

Who knew?

25th June 2012

Chris Kenworthy

What it comes down to is being brave enough to shrug off that comfort blanket of a predictable salary, workload and future. For me, that so-called ‘comfort blanket’ slowly became more suffocating and my reward for going freelance as a copywriter was a chance to seize control of my own fortune.

Are desk jobs even that secure any more? I’m hearing more stories about people going to work to find there’s no job for them anymore. I’d rather be in charge of my own destiny – if you fail sometimes at least you have the chance to learn from your mistakes and know when to change course in the future.

You’ve inspired me to write my own take on the questions you’ve asked. If only I can overcome the fear of exposing myself.

26th June 2012

Fear of freelancing | Chris Kenworthy

[…] Nattan’s ‘Fear of Freelancing’ post on The Professional Copywriters’ Network opened up a few old wounds (as you might have […]

3rd July 2012

Mike Beeson

I launched myself as a copywriter many years ago. In those days, I was a young man so I knew no fear. As I’d always wanted to be ‘a writer’ in some shape or form, the insights I’d gained working in a big ad agency persuaded me I could do it. So I did.

The difference between then and now is that there weren’t many freelance copywriters around back then. That was because it was pretty well essential to have ad agency experience, which I had. Being on the inside track meant I spoke the language of the people in ad agencies so I got the work. Plenty of it.

Now, it seems, almost anyone can become a copywriter. Much of the work is fairly straightforward. It doesn’t always require business insight or the ability to think conceptually. With so much ‘content writing’ around, it doesn’t call for much thinking of any description.

Would I go freelance now if I had a steady job? The answer is a combination of: “No thanks. The economy is in a bad way so where will I find clients prepared to gamble on a newbie?” My other answer might be: “Yes please. I believe in my ability and I have to follow my star. What’s money got to do with it!”

20th July 2012


Wordtracker has just published an article on how freelance writers can win more business.

The focus is on writing copy that can help increase your sit’s position in Google’s search rankings, as well improving conversions from visitors once they reach your site.

The article shows how your copywriting skills combined with a minimal understanding of search engine optimization can help you win more business:

It’s ideal for anyone starting out on a freelance career. I hope that’s helpful.

7th January 2013

4 simple steps to overcome the fear of freelancing

[…] may face before even starting out, I recommend reading this article from Freelance Folder, and this one from The Professional Copywriters Network. For advice down the road, for what to do in freelance […]

9th January 2013

John Mc


Nice piece, and I’m up for writing that follow-up post you mentioned.

When I was mulling over whether to go it alone, a freelance colleague said me something that’s stuck in my mind ever since:

People often worry about not having the security of a full-time job. But actually, in this day and age, job security is often just an illusion. It’s relatively easy for your employer to make you redundant – and if you move jobs regularly (like many people do), you’re unlikely to be entitled to a big redundancy payoff.

I’m not sure I totally subscribe to that view, but I do think there’s some truth to it. If you stop and think about it, how secure is your job, really?



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