7 Common Reasons Freelancers Fail (And How to Avoid Them)

by Tom Ewer 5 Minutes

The word "Great" nailed to a wall, with the letter "A" askew.Freelancing is by definition an insecure profession, and many people hesitate before they enter such a competitive environment for fear they won’t match up. Others try, and find they struggle to make it.

Intriguingly, it’s not just the obvious reasons that end budding freelance careers, such as poor quality of work or a tendency to miss deadlines. Below, we’ll look at seven of the main reasons why freelance careers fail to take off, and how you can avoid these traps. Let’s go!

1. Failing to Organize

When working for an employer, you already have a structure in place – often a very rigid one, which you fit into almost without thinking. The entire framework for your work is there.

When you go freelance this support is suddenly gone, and it’s easy to fall into a disorganized mess which makes it impossible to work well or efficiently.

To organize, look to apps. Invoicing software such as FreshBooks streamlines one major freelance headache, and there are some great time management tools such as TeuxDeux. RescueTime very usefully lets you analyze how you spend your time on the computer, and can block distracting websites.

If you are really bad at time management, focus booster is an online timer using the Pomodoro Technique to set 25-minute work periods, followed by a five-minute rest period as a way of helping you to divide up the day. If you need to keep track of how long you’ve spent on a task, Toggl can be very helpful.

2. Giving in to Stress

There are apps out there that can provide a basic service along any line you care to think of, including yours, and there will always be cheaper products or services. Furthermore, competition can be intense – particularly if you haven’t thought carefully about your niche. However, you cannot allow yourself to be ruled by fear.

To succeed as a freelancer, you’ll need to persevere – look beyond the fear, and tap into your passion for your work. You’ll need to research your market, accurately identify your target clients, and search out your own motivation.

Be honest with yourself about your strengths and weaknesses. If you really feel you can’t judge yourself, try asking a previous employer or client that you’re on good terms with for a truthful recommendation you can use, and learn lessons from it yourself.

3. Failing to Stand Out

Freelancing is very different to working for a company; you have to be able to sell yourself, and create your own brand. If you don’t stand out from the crowd, your voice (and business) can easily get drowned out.

Start by making a ‘life list’ of achievements you can highlight in a pitch. On top of academic qualifications, you need to think more widely about what you’ve done with your life. You can prove your organizational skills, for instance, by highlighting positions of responsibility in clubs or other groups.

Having a niche really helps – while this means some general posts may pass you by, the numbers pitching for those projects probably mean they will be tough to win anyway. Specializing gives you an edge for projects that do fit your profile.

You could also use Bidsketch (naturally!), who provide a very effective means of impressing clients with your persuasive proposals, including custom client landing pages, great templates, and electronic signatures to facilitate fast turnaround.

4. Failing to Set the Right Rate or Time Scale

Every successful freelancer has a minimum rate they can work for, and the ability to estimate project timescales with reasonable accuracy. Both are critical – if you get the rate or the timescale wrong, you can end up losing serious amounts of money.

There’s a basic equation to work out your hourly rate, involving adding all of your work-related expenses (including essentials like supplies, electricity, mortgage, etc.) and the days and hours you intend to work on average (minus vacation days, plus a small allowance for sickness), plus retirement funds, and the profit you’d like to make.

Then, you have to estimate the amount of time a project will take if you’re working to a lump sum rather than a per-hour rate (there is a big argument about which is better, if you look at this previous post).

Apps from the likes of Motiv automate this process – you fill in all the boxes and it calculates your hourly rate and annual salary. Job done!

Remember that different clients may require different prices – commercial clients can be charged more than not-for-profits, for example. As your experience increases, your rate should also go up.

5. Failing to Think Through Expenses

Expenses are a classic issue. Many freelancers forget some of their expenses when they start out, and this can make the difference between success and failure.

Apps such as Expensify can be very helpful – it lets you take photos of receipts on your phone and convert them into a neat report, and it’s free for individuals to use. On a larger scale, the online platform inDinero allows you to keep track of expenses, and pull information in from bank and credit card accounts, to provide a snapshot of your finances or predict future spending.

Free online invoicing and billing service Hiveage can automatically accept payments and issue bills, and payment giant PayPal is now offering a billing service itself. Finally, when you’re sealing that deal, Shake has a library of business contract templates geared towards freelancers that you can use to create legal documents.

6. Disliking Change

As a freelancer, you really have to be flexible. You have to chase the work, because it won’t always come to your door, and that means keeping up with trends and making sure you’re ahead of them. The word “rusted” is sneakily hiding in the phrase “tried and trusted”…

If you want to keep up with events, sites like LinkedIn, the Freelancers Union, this very blog, and trade associations will give you useful insight into developments across a wide range of relevant issues.

7. Needing Company

Freelancing is a lonely business. If you’re busy, it’s easy to go for weeks without meeting anyone apart from your cat. People who really can’t do without company often find this aspect of freelancing unendurable.

There are ways around this though. It’s increasingly possible to rent a desk – you can find local opportunities through websites like Deskcamping or Desks Near Me, which let people with office space make contact with freelancers who really like the office environment (or vice versa).


Freelancing is a great way to work, but you have to avoid various issues that can trip you up and cause you to fail. Equally, there are lots of hacks to keep you on track. These include:

  1. Failing to organize: There are loads of apps to help.
  2. Giving in to stress: Get past clients to assess your strengths.
  3. Failing to stand out: Find a niche that suits you.
  4. Failing to set the right rate or time scale: Work this out carefully.
  5. Failing to think through expenses: Use online resources to check.
  6. Disliking change: Keep up with trends through relevant websites.
  7. Needing company: Try desk camping!

What other potential failures do you see, and how do you avoid them? Let us know in the comments section below!

Image Credit: Dr John2005.

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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.