As a freelancer, what’s your biggest challenge?

Posted on: March 10th, 2014

In the 23 years since I started freelancing (I know, I know, that’s a really long time…), I’ve faced many challenges along the way. In no particular order, they have included:

  • Clients are REALLY slow to pay, seriously impacting my cashflow.
  • Clients reschedule projects that clash with others already in my diary.
  • The cycle of feast and famine (linked to above). One month I may have very little work on and the next I don’t know how to cope with all the projects that are being thrown at me.
  • Clients don’t keep to their side of the schedule but the end deadline can’t move.
  • Clients decide to bring the project in-house in order to ‘save money’.
  • Clients go bust, owing me money.
  • I turn work down because I am fully booked, only to find that a project from another client is then put on the back burner or cancelled completely. (Seriously annoying, that one!)
  • A senior person on the client side decides to get involved when the project is well underway and completely moves the goalposts.
  • Technology fails on the day when there is an urgent deadline (never happens on a Saturday morning).

Yes, these are just a few of the challenges I face in my life as a freelance copywriter. And I am sure you will be all too familiar with many of them.

Note how many of the above bullet points start with the word ‘clients’. Don’t get me wrong, I really enjoy working with my regular clients and have worked with several of them for well over ten years. Without them, I wouldn’t have a business.

No, it’s the ‘one-offs’ that cause me grief. Over the years, I have tried to learn my lesson over who to work with and who not to work with. If a little warning bell goes off in my head that I think may result in something from the list above, then I make sure I listen very carefully to that bell and say ‘no’.

What are the biggest freelance challenges you face at the moment?


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7 Responses to “As a freelancer, what’s your biggest challenge?”

  1. Annie Brooks
    March 11th, 2014

    Interesting list Carole and I have to say not necessarily limited to a freelancer. As a small business owner we have experienced many of the above. Especially when running our branding consultancy. However sometimes it’s very empowering to say no. Difficult. But empowering. I wouldn’t be surprised to find that your regular clients will wait for you if you are busy because they value what you do. It’s the one-offs who often cause the biggest headaches. That’s why it’s imperative to build relationships in business. Then you become the supplier of choice for your clients because they know you, value you and love what you do.

  2. Carole
    March 11th, 2014

    Over the years, I’ve found it much easier to say ‘no’, Annie. Because when I used to ignore the warning bell clanging in my head, I always regretted it. Now when I say ‘no’, I know I’ve made the correct decision. And I can fill that empty space with a project I’m going to enjoy.

  3. Nicola Fisher
    March 13th, 2014

    I absolutely agree with this article and with Annie, not just a freelance issue! In the 15 years that I have been running a business one of the hardest things to learn is saying no. It doesn’t have to be a big warning bell – that little niggling doubt about a client nearly always has a reason to be there. And it usually ends with issues over payment or a design that you really aren’t happy to put your name to because they are so difficult to work with.

    Saying no can bring respect and understanding of how you work, and we have had prospective clients come back to us when they realise that a clear no nonsense business relationship really is something to value!

  4. Carole Seawert
    March 13th, 2014

    Hi Nicola, I know someone who runs a small agency who, after meeting with a prospective client for the first time, works out what the hassle factor might be in working with them and prices the project accordingly! The more tricksy they appear, the higher the price. I’m not sure that extra dosh is worth the grief, tho.

  5. Gustavo
    July 24th, 2014

    One of my biggest challenge as a freelancer is getting paid on time. I recently started using this new tool and the results are great! I now have one less thing to stress about.

  6. Lindsay Jacobson
    June 9th, 2016

    I have been a Freelance Graphic Designer for almost two years after working for a small printing company, and as a Marketing Coordinator for a Law Firm.

    As a freelancer, my biggest struggles are:

    Managing time effectively to make sure I am balancing all important aspects of running my business. I spend the least amount of time actually designing, most of my time is spent working on passive income, reading and education, finding clients, working on promotional and strategic marketing, accounting, and communicating with existing clients
    Negotiating rates and chasing payments. I hate dealing with the money side of things; quoting rates for a project is never easy no matter how much I do it. Also, I invoice my clients using Freshbooks, and sometimes invoices get lost or go to spam filters (thanks programmers of Freshbooks!), so I always get anxious whenever I send off invoices.
    Managing personalities and expectations. Learning what the client wants and expects from me, sometimes having to read minds, dealing with people who can’t make decisions, or don’t know what they want.
    Isolation. I love the freedom freelancing affords, but working alone all day, everyday sometimes makes me nostalgic for the long lost days of office banter, distracting co-workers, and the camaraderie of working in an office. Sometimes I will go days without having an actual real life conversation with another human—so watch out first person I have contact with! I saved up all my thoughts and experiences to verbally dump on you—hope you like it!
    Convincing clients of the value your skills offer, being an “expert”, getting good, high paying clients. With the internet being a global marketplace, one can get design services and products at any price range, often for very low cost. Competing with freelancers in India who work for $4/hour can be tough, or the fact that everyone with a computer and access to google images thinks they are a designer. I have to constantly sell my skills and the value they offer in order to get paid a fair rate. Never ends.
    Besides the challenges I face as a graphic designer, I still love design and have a grateful heart that I can use my skills to work for independently. My love for creative expression and design, makes all the headaches, pressure, nightmare clients, and self-doubt worth it!


  7. Araix
    August 2nd, 2016

    I am trying my best to get myself into a routine, although making it flexible enough that I don’t feel like I’m working 9-5 for an employer. That said, I find myself often working late, and then when I get in bed my brain is still active and I cannot sleep, so I end up going to bed at 1 or 2 in the morning; which has an impact on the next day.

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