5 freelancer nightmares: the top hurdles you face and how to deal with them

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Freelancers face a lot of challenges in their day-to-day lives. To help understand these challenges at an in-depth level, we went directly to the source: our freelancing community! 

In this article, we are going to present answers from over 1,800 participants in our most recent survey. We asked, “What are the biggest challenges for freelancers?” and you responded. 

The results show a comprehensive picture of what a freelancer faces – finding clients and projects, making sure you get paint on time but also enjoying the work you do. 

Here are the top obstacles in a freelancer’s life and some tips on how you can avoid them.

These are the results of our 2018 freelancer survey. Every surveyed freelancer had the chance to pick their 3 biggest challenges and back then, the 3 major challenges and freelancing problems were:

  • Landing clients – 31%
  • Separate private life and work / work-life balance – 18%
  • Getting a better payment – 17% 

Freelancing problems and major challenges freelancers faced in 2018
Freelancing problems & challenges – Freelancer survey 2018

In 2020, we ran our yearly survey again, asking the same question. And here are the top obstacles that a freelancer faces in 2020:

Freelancer obstacles for freelancers - 2020 Results
Freelancing problems – Freelancer survey 2020 Results

1. Landing clients

Project acquisition was, by far, the most commonly-faced challenge in our community. About a third of you chose that option as the biggest issue in their career (68% in 2020!). 

This does not a huge surprise; at its core, freelancing dictates client acquisition to be a top priority, regardless of industry or previous success.

So how do you land clients more easily? 

  • Activate former clients: To avoid always looking for new clients, make sure you build lasting relationships with the ones you are currently working with. Most successful freelancers get recurring jobs from the same client.
  • Have a system: Coming up with a new way to approach clients each time you need a new project can really grind you down. Make sure your efforts are not wasted. Track the ways in which you approach clients and measure how successful they are. Once you figure out what works best for you, settle on a method, and continuously refine it. By doing that, you’ll create a system that’s tailored for you and will keep getting you clients with minimal effort.
  • Don’t give up and avoid slowing down: Persistence is key when acquiring clients. You don’t want to live project-to-project with periods of no contracts in between. Always be on the lookout and always follow your system. Having more projects means you can pick the best ones, too. Even when your plate is actually full – this is one of the rare circumstances where more is almost always better.
  • Be active on social media: Engaging on social media is one of the best ways to source projects and land clients in 2020. It is great for both networking and for showcasing your skills.

    – Someone tweet something related to your field of work? Share your ideas or give feedback.
    – Is someone looking for a freelancer with your skills? Share your portfolio!


    Build real connections with other freelancers and do not hesitate to recommend them to others when appropriate! They might return the favor someday. 
Portfolio Dragos Muntean

 2. Work-life balance

More than one-sixth of our participants said they struggled with work-life balance in 2018 and 2020 saw this number jump to nearly one-third of all surveyed freelancers.  

Let’s be honest, nobody likes to admit that their personal life is suffering because of how much they’re working. At the beginning of your career, it can be very tempting to put your foot on the gas pedal and never ease up. But even if you love your job with all your heart – you need a break.

Take it when the opportunity arises.

As a freelancer, you need to learn to say no and also turn down freelance work when you simply cannot take on. It’s important that you manage a healthy work-life balance.

So: Don’t sacrifice your sleep. Be there for your friends and family. Burning yourself out after a couple of years of freelancing is the easiest way to make sure your career doesn’t go far.

3. Getting a better pay rate

This is another classic freelancer struggle that everyone goes through at some point. 

About one in six of our participants said that increasing their pay rate is the biggest challenge they’re facing. As a freelancer, if you are consistent in learning new tools and techniques and bettering your skills every year, you expect to see this growth in skill coincide with a growth in pay. 

In reality, however, many freelancer jobs are part of the punishingly-competitive markets. This means there will be a lot of people trying to undercut your prices. The best way to combat that is to go against the flow. 

Avoid lowering your rates just because there are ten other freelancers in your niche who would do the job for less. Emphasize quality instead

As freelancing keeps growing, many businesses realize that it’s not just about cheap and convenient external labor – it’s about getting experts. Strive to be one of those experts and make your payment reflect that.

Recommended read 📖 : Negotiating a freelancer raise – Tips & Letter Sample

4. Staying productive

More than 15% of our survey participants say they struggle most with maintaining productivity. There are a lot of ways to fight your laziness and you will have to look for one that works best for you.

Some people find that working in an environment with other people gets them motivated. This could be your local library, a co-working space, or the coffee shop around the corner.

The best way to figure out how you can maintain self-discipline is by trying different things out. If you see that things aren’t working out, break the mold.

  • Not a morning person? Stop trying to push yourself to work at those times altogether and focus on the evenings. 
  • You can’t get any work done because emails keep distracting you? Turn off your phone and the email client on your laptop. 

Identify what distracts you and cut it out as much as you possibly can. Eventually, you will arrive at a place where you understand how and when you work best; utilize that knowledge to become more productive than ever before.

Some ideas that can help freelancers with their productivity:

  • Create and follow a to-do list: Prioritize your tasks and plan your day upfront to understand all things you should complete in your working day.
  • Use project management tools: There are many online tools that can help you organize your life and business so that you can keep track of client acquisition, the tasks you need to complete for each client, etc. Trello can be a great option for freelancers.
  • Time-tracking tools: If you work with clients on an hourly base, the client might ask you to use a particular time-tracking tool such as Toggl or TimeDoctor. Familiarize yourself with these platforms!


Join our IT freelancer community today! Create your freelance profile in just 2 minutes.  


5. Accounting

Running a business involves a lot of paperwork and requires time to manage invoices, chase payments, submit taxes, etc.

Accounting, in particular, was also cited as a big challenge for 21% of freelancers. This is usually one of the tasks freelancers prefer outsourcing. If you can afford it, this is a great option.

However, you could also explore one of the many accounting apps available to freelancers. Many allow freelancers to track time and handle invoices or expenses very easily, which can save tons of time. Some accounting software option to consider:

What are your biggest freelancing problems? What do you struggle with in working freelance? Share your thoughts with us in the comments below!

Natalia Campana

Natalia is part of the international team at freelancermap. She loves the digital world, social media and meeting different cultures. Before she moved to Germany and joined the freelancermap team she worked in the US, UK and her home country Spain. Now she focuses on helping freelancers and IT professionals to find jobs and clients worldwide at www.freelancermap.com

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By Natalia Campana

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