Leaving Work Behind

Five Freelance Writing Nightmares (and How to Deal With Them)

Written by Lis Stedman on March 24, 2016. 15 Comments

A woman waking from a nightmare.It’s 3am and you wake up in a cold sweat, torn away from a terrible nightmare. What was it about? Some TV monster? Justin Bieber? No – it’s your freelance writing career.

What are the problems that keep you awake at night, and what’s the best way to deal with them? Here are some thoughts – both on the types of things that freelancers worry about most, and useful solutions.

1. Clients

Funnily enough, if you Google “freelance nightmares“, pretty much every example that turns up is related to clients. Considering we all need clients to survive, this is not good news.

Things start out so well – after all, all clients are good, right? Wrong. There are clients who want to send you messages at all hours of the day and night, clients who throw tantrums, clients who try to slide in extra work for no extra pay, and even clients who simply forget to pay – sometimes this month, sometimes at all.

So how do you cope with the hideous range of possible client-related catastrophes that could befall you? The answer is to take back control. Don’t ever think that a situation will somehow improve if you ignore it.

First of all, check your contract – and you do need a contract for regular work, so that if things go wrong you have legal backup. This should clearly set out the detail of what you’re supposed to do, in terms of the extent, remit and process, as well as when and how much you’ll be paid.

Unless you really love a client, you need to set limits. Let your clients know what your working day is, and stick to this when practically possible. If clients try to slide in extra work, explain in return how much extra it will cost.

For non-payers, a reminder is in order when they go beyond the terms agreed in your contract. Follow up a week or two later if you don’t hear. If they still don’t pay, and you suspect they are trying to get out of paying altogether, you can always use the threat of the Small Claims Court – this is a reasonably simple and cheap way of recouping small amounts of money in the UK. (Perhaps there is a similar setup in the US?)

I would definitely recommend joining the National Union of Journalists (NUJ) if you’re in the UK, or an equivalent body elsewhere. The NUJ has a freelance section and a legal team – a great help when things go wrong.

2. Money

Oh yes, money – the root of all evil and sadly, the root of all rent and mortgages, not to mention food payments. If this one hasn’t given you sleepless nights, you’re probably not a freelancer.

So what’s the best way to make sure the bills get paid? A lot of freelancers would advise that if you’re starting out, you should keep at least a part-time job while you’re building up a client list.

That can be hard work, but at least you’ll have regular money coming in. The other advice, if you already have clients, is to diversify – don’t put all your hopes (and financial trust) in one or two big clients, however wonderful they may seem.

A range of smaller clients may well be better in the long run – if one goes, the overall effect isn’t so dramatic. Try to build yourself a financial cushion of a couple of months money to pay your bills, so that you have time to find other opportunities if the worst happens.

3. Deadlines

Deadlines are like buses – sometimes they all come at once, and on top of this you’re bound to have one client who absolutely needs an urgent, two hour phone discussion right on your busiest day. Being a freelancer, you’re going to find this happens sometimes – just as sometimes, there won’t seem to be any work at all to do.

Organization is critical – make sure you have an organizer in which you can easily see what work is due on any given day. And if you have work you can do, do it – no matter if the deadline is weeks away, if you have spare time, it pays to finish whatever is to hand.

The free Wunderlist app is a simple list-based reminder system that sends you emails when you have a deadline – it’s fairly rough and ready and works by day rather than time, so you can’t use it to remind yourself when a phone call is due, but it’s fine for date-based deadlines.

The Google Calendar app is great if you have a team to organize, because you can synchronize calendars and layer everyone’s calendars in a single view. If you have a Google account there is also a simple event reminder app, which is quite detailed enough to input freelance deadlines and appointments.

4. Distractions

Working on your own isn’t easy. Just when you are in the middle of an important phone call, the doorbell will ring. Or emails, pets, partners or young children will intervene. Every day you say you’ll get more done, but it doesn’t happen.

Start by prioritizing your work so that the most urgent tasks get done. If there’s a time of day when you do certain tasks best, schedule them for that time and ring fence it. If you really need to work on something that requires concentration, you may have to disconnect the internet and your emails and leave your phone in another room.

Create mental boundaries for yourself – allocate times when you can answer emails and do all the distracting tasks like checking Twitter, even if that means setting time aside per hour. You could also set physical boundaries – having a room dedicated as an office can help to put you in the right frame of mind.

5. Juggling Too Many Tasks

We all find ourselves juggling work, family commitments and our social life, but having too much on your plate generates stress and ultimately ill health, so the experts say.

If you are under too much pressure, write down a list of what you’re actually doing and the priority each task has in your life. This can help you to see what’s important, and what isn’t.

Learn to say no – try only to take on tasks that help towards your goals, and either avoid the rest or delegate them. Try to completely focus on doing one thing at a time – once you’ve prioritized your work, this should become easier.

Take real breaks, away from your desk and your phone, so your mind gets a chance to be still. Make room in your life for those things that energize you – hobbies, family, and ‘me’ time.


The life of a freelance writer can be stressful, and you can find yourself losing sleep over bad clients, lack of funds, tight deadlines and actually, how to get the work done and how to finding time for yourself.

Try to focus on having coping mechanisms in place so that, where possible, you have organized out the weak points in your day-to-day life and given yourself the best chance possible of achieving your priorities.

Hopefully, when you’ve done that, you’ll get a sound night’s sleep! Just don’t think about Justin Bieber…

Have you had any freelancing nightmares? Do you have any tips to deal with them? Tell us more in the comments section below!

Image credit: thewebprincess.

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15 Responses to “Five Freelance Writing Nightmares (and How to Deal With Them)”

  1. Robert
    March 24, 2016 at 4:44 pm

    This is a wonderful article for both new and older freelancers. It doesn’t matter how long you have done the freelancing thing, you will always have these crazy nightmares. The key is to not let them rule your career!

  2. Khalid Karem
    March 24, 2016 at 8:08 pm

    this 100 percent true. it goes more what you said here in Egypt. specially those who don’t pay

  3. Katherine
    March 28, 2016 at 9:28 am

    I totally agree and I find this very useful. Of course we all do have the same issues with clients and not only. Thank you for tips!

  4. Elvis Michael
    March 28, 2016 at 6:29 pm

    Number 3 and number 5 are my biggest enemies, but I am also learning to cope.

    Finally, although I am gradually straying away from writing, I am also looking to get 1-2 bigger clients as opposed to having several small ones. This opens up more room on my weekly schedule, overall.

    Thanks for yet another wonderful article, Lis!


  5. atika
    March 28, 2016 at 6:46 pm

    I am freelancing since 7 to 8 years. Now currently working as an editor. I love my job but it is low paid i guess. I have planned up on starting my own blog…but trust me, I am getting serious nightmares. It maybe because of the need to get an urgent boost. Well, let’s see

  6. John Mac Hayes
    March 28, 2016 at 7:56 pm

    Wow, I didn’t realize freelancers went through all of this. I sure hope I am not one of those clients you fear.


    • Tom Ewer
      March 30, 2016 at 9:00 am

      I think, John, that by reading the Leaving Work Behind content you’re developing an understanding of the other side of the fence, so to speak. That definitely holds you in good stead 🙂 Thanks for your comment!

  7. Akinde Hafiz
    April 7, 2016 at 2:25 pm

    Thanks Tom for these practical pieces of advice.

    To get lot more done and beat deadlines, identifying the most productive period of your day helps us achieve the most important tasks.

    Also, we should be applying the Pareto principle a lot. This principle explains how 20% of actions can be used to achieved 80% of the job.

  8. Ash
    April 8, 2016 at 8:19 am

    I Can’t help but agree with each of your points on “nightmares” that come with “freelancing”.

    I managed to find my own ways of dealing with each of those, including


    Only choose to work with clients who respect you for what you do. Anything else won’t do. So screen clients out


    People? Politely & firmly, let them know that you can’t be disturbed. Internet? off. Phone? Off. Everything else? off.


    Learn to manage it. Work to get more just when you think you’d get less.

    Or so it goes…

    • Tom Ewer
      April 8, 2016 at 8:44 am

      Ash, you’re right – there’s no cookie-cutter approach, and you have to find a way that works best for you. Thanks for your comment!

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