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Overcoming 6 Common Freelance Challenges

Daena Skinner
June 25, 2024
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Overcoming 6 Common Freelance Challenges

The way we work is changing. Amid rapid economic changes and the growing availability of remote, more and more people are choosing to forego traditional full-time jobs and go freelance. Consequently, it’s estimated that there will be 1,57 billion freelancers working worldwide in 2023

However, just because something is popular doesn’t mean it’s easy. As a freelancer, you’re the owner, manager, and employee of your own one-man business. And as you can imagine, that comes with its fair share of challenges. 

But that’s why we’re here. In this article, we’ll break down the 6 most common freelance challenges and how to solve them. So, whether you’re an established freelancer, just looking to start out, or part of a company trying to figure out what makes your freelance workforce tick, this piece is for you. 

Solving the 6 Most Common Freelance Problems

Challenge 1: Finding the Right Clients for You

Unless you have a long-term arrangement with your client(s), ensuring a steady revenue stream for your freelance business can be very difficult. And clearly, that’s a problem, because you need to put food on the table somehow. 

The good news is that there are plenty of freelancing job posting sites nowadays, UpWork being one of the most popular options. Here you can find available projects and send your pitch, or create a portfolio, advertise your services, and wait for clients to come to you.

The bad news is that doing this doesn’t necessarily guarantee you getting any work. Furthermore, projects from UpWork and similar sites don’t tend to boast the biggest pay-check, though it can still be a good place to get started. But if you want to take your freelancing business to the next level, try the following steps:

  • Define Your Target Audience:
    If you know your strengths, you should be able to estimate what kind of client they’d benefit most. Consider the industry, company size, likely needs, and expected budget.

    Based on these metrics, we recommend you create an ICP (Ideal Client Profile) and expand it into a desirability spectrum. This’ll allow you to evaluate projects faster, as well as market yourself to your target demographic more effectively.
  • Cultivate a Relevant Portfolio:
    Now that you know who you want to work for, creating a portfolio that’ll resonate with them is time. Highlight work experience that showcases your relevant technical know-how, understanding of processes, and just pure skill in your niche. 

    If you have none (for now), it’s a great opportunity to get your hands dirty with a freelance job posting portal, as mentioned above.
  • Create a Social Media Presence:
    Your clients are only human, too, meaning many spend a lot of time on social media. This is your ideal opportunity to catch their eye and get into “the talks”. Use social media tools to help you post and engage consistently with your desired audience.

    Facebook freelancing groups are a good place to find low-hanging fruit. But for the juicy job offers, we recommend interacting with your target clientele on LinkedIn. Comment on their posts, send messages, or offer a free trial run of your services. This approach can effectively enhance sales lead generation.

    In addition to establishing a social media presence, creating visually appealing content is crucial to catching your audience’s eye. Alternatives of canva are an excellent tool for this purpose, offering a wide range of templates and design elements.
  • Network with Fellow Freelancers:
    You can never have too many friends. And that’s especially true in freelancing. By keeping your finger on the pulse of your niche’s freelancing community, you can access valuable info or even projects you wouldn’t know about otherwise.  


Pro tip:
Easily schedule your client meetings as a freelancer with Simplymeet.

Challenge 2: Setting Appropriate Rates

So, you’ve found someone willing to take you on for a project. The question is, how much should you charge? Ask for too little, and you might devalue your work too much and struggle to make ends meet. But ask for too much, and the client might choose to drop you. Unfortunately, there’s no right answer for everyone, but these steps can help you find your price. 

  • Understand Your Niche:
    Software developers make more than copywriters, and enterprises have bigger budgets than SMBs – that’s just how things go. To accurately gauge the price range you should target, you’ll need to consider the industry, company size, your profession, as well as the complexity and length of the project itself
  • Know Your Worth:
    Fresh-faced freelancers often undervalue their work to get whatever client they can. While this can be an effective short-term strategy, there are several things you should consider. Namely, your seniority level in your field, the quality of your output, and how quickly you can deliver.

    Furthermore, raising rates is never easy, and your customers will definitely object if it’s a big jump in price. Therefore, it’s better to set your costs in the ballpark of what you’d be happy with right from the start, prove your worth, and then go up in smaller increments.
  • Consider Your Expenses:
    It should go without saying, but every business’ goal is to make money. Digital-only freelancers may not have many expenses to speak of, but that’s not the case for manual laborers.

    If you work in a hands-on environment, have to travel for your work, use your own equipment, or provide materials vital for the project, you need to add these factors into your calculations to not cut into your bottom line.
  • Be Willing to Negotiate (But Know When to Quit):
    Unavoidably, you’ll bump heads with clients regarding your rates. But usually, you can find a middle ground that’ll satisfy both parties. Be sure to explicitly explain to your potential customers why you charge whatever amount, but be receptive to their position. 

    And remember, if you can’t find common ground, sometimes it’s better to quit while you’re ahead and look for a client that’ll understand the value you bring. 

Challenge 3: Managing Finances Efficiently

Even small businesses need to manage their finances to stay efficient. In truth, there’s a lot to worry about. From tracking time, income, and expenses for tax purposes, issuing invoices, quotes, and estimates; to keeping tabs on late payers.

Thankfully, nowadays, you don’t have to do any of this by hand and automate a great deal of your book-keeping with invoicing software for freelancers. Although finding one that’ll work for you might take a bit more effort, it’ll be all well worth it in the end. Here are just a few of the benefits:

  • Quick and Easy Invoice (and Other Document) Creation (freelance invoice templates)
  • Faster Billing and Payments
  • Comprehensive Financial Reporting
  • Secure Cloud Encryption
  • Remote Access via Desktop and Mobile Apps
  • Reduced Paperwork
  • Lower Investment in Time and Money
  • and more.

Diving into the entire process would take too much time, and since we value your time, we won’t dilute this article too much. In short, here are the 8 steps you should take when looking for a freelance invoicing or book-keeping solution for your freelance business.

1. Specify Your Needs
2. Set a Budget
3. Read Reviews
4. Value Ease of Use
5. Consider Security
6. Check for Compatibility with Other Tools
7. Look for Great Customer Support
8. Combine It All & Choose the Best Package

If you’re searching for the top productivity tools for freelancers, read this article.

Challenge 4: Balancing Work & Personal Life

One of the biggest freelance challenges is finding the right balance between your work and personal life. On the one hand, you can work anytime and anywhere you like. On the other hand, that means you never really clock out and end up working all the time. 

If you’ve freelanced for any time, this’ll sound familiar. You’re out with friends or your family when suddenly your phone beeps. It’s a message from a client, and just like that, you’ve been forcefully pulled out of the moment and into “work mode”. Or possibly, your freelance problem is the opposite; try as you might, you can’t focus on work at all.

Whatever the case, here are some freelancer life hacks to help you overcome these issues:

  • Change the Scenery:
    If you struggle balancing your work and personal life, one of the most effective things you can do is create a physical barrier between them. You can convert one of your rooms into an office if you have the chance, or alternatively, you can opt to work from a café or coworking space.

    By only working in specific conditions, you can create associations that’ll convince your brain to automatically kick into work mode without spending ages focusing and returning to normal as soon as you leave.
  • Own Separate Devices:
    Similarly, you can divide your work from your personal life even further by having a work PC and phone, which you use for nothing else. But if that’s not quite within your budget, you can always settle for just having separate profiles on your devices.
  • Set Strict Business Hours:
    Another thing that’ll stop you from half-assing everything all at once and focusing on one thing at a time is just that – time. Define when you work, and outside of that, ensure all your work-related notifications are turned off. It’ll do wonders.

Challenge 5: Keeping Mentally Healthy

Continuing from the previous topic, mental health is one of freelancers’ biggest problems. Unsurprisingly, you don’t tend to have too many opportunities to socialize as a one-man show working from home. Unless, of course, your pets or the voices in your headcount.

Thankfully, there are several things you can do to help you maintain mental health while keeping you professionally efficient. This includes joining online communities of other professionals from your field, working from a co-working space at least once a week, or getting involved with your local conferencing scene. 

Challenge 6: Dealing with Difficult Clients (and Coworkers)

The last common freelancer challenge we’ll tackle in this article is one that can potentially throw the biggest wrench into your operations – other people. Unlike software and processes, humans don’t tend to be logical or reasonable. But as always, there are a few ways you can deal even with the most difficult clients and coworkers. 

  • Stay Calm and Professional: No matter how difficult the person you’re dealing with may be, staying calm and professional is important. Avoid getting defensive or engaging in arguments, and try to find common ground or a mutually beneficial solution.
  • Set Boundaries: If a client or coworker is consistently overstepping boundaries or making unreasonable demands, it’s important to set clear and firm boundaries. Be clear about what you are and aren’t willing to do, and don’t be afraid to say no if necessary.
  • Communicate Clearly: Effective communication is key when dealing with difficult clients or coworkers. Be clear and concise in your messages, and try to anticipate any potential misunderstandings or conflicts before they arise. And don’t forget to listen actively to their concerns and feedback as well.
  • Document Everything: When dealing with difficult clients or coworkers, it’s important to document everything that happens. Keep a record of all conversations, emails, and other communications, as well as any deadlines or agreements that are made. This can help protect you in case of any disputes or misunderstandings down the line.
  • Know When to Walk Away: Finally, if a client or coworker is consistently causing stress or making your work life unbearable, it may be time to walk away. Remember that you have the power to choose who you work with, and it’s okay to say no to clients or projects that aren’t a good fit for you.
  • Follow up with clients with due payments: If a client has not cleared their past dues, it’s important to send them timely payment reminders via email. This helps maintain clear communication and encourages prompt payment. Be sure to include the amount due, the original invoice date, and any late fees that may apply. You can also offer convenient payment options and provide a direct link to the payment portal to make the process as smooth as possible for your clients.

Learn how to generate more leads for your freelance business.

Summing Up:

Clearly, despite its popularity, the freelancing lifestyle isn’t the walk in the park it might first seem. Then again, nothing ever is, and the sense of freedom and personal accomplishment might well be worth dealing with these common freelance challenges. 

And with the solutions to freelancer problems outlined in this article, you should be ready to make this lifestyle work for you and thrive, not just survive. Remember to take your job seriously, respect your clients, and value your time and expertise. Use every tool available to your advantage, and don’t forget to take care of yourself.

Author Bio:

Rudolf Marejka
Freelance Copywriter

Rudolf Marejka works as a freelance content specialist for global startups.

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