The 4 Biggest Freelance Challenges

Have you ever considered a career as a freelancer? 

If you’re anything like me, writing for clients from around the world while wearing your favorite yoga pants for 10 hours a week sounds like a dream.  Freelancing has been an interesting and exciting ride, but it’s not without its freelance challenges.

When I started my freelancing journey, I thought I’d be in a position to quit my 9 to 5 and retire as a self-made millionaire within six months to a year. 

It’s been six years and I’m not quite a millionaire yet, but deciding to become a freelance writer is one of the best decisions of my life. I’ve learned to navigate the pros and cons of freelancing in order to build a successful freelance business.

Read this guide to learn about potential freelancer problems you might face in this industry and how you can avoid common freelancer struggles. 

What are the Biggest Freelance Challenges Freelancers Face?

Some of the biggest freelancing problems you’ll face are not having enough clients and experiencing freelance money challenges. Or, you might have too many clients and not enough time to manage them. That’s why the phrase “feast or famine” is often thrown around freelance communities.

As a freelancer, you’ll constantly juggle life between a rock and hard place, that is until you learn the number one golden rule to keep your pipeline and bank account flowing constantly.

How do I find freelance clients?

This is one of the most common challenges as you explore how to become a freelance writer. Finding freelance clients will be one of your biggest freelancer struggles. For many freelancers, talking to potential clients about your services can send them into total panic. (Freelance imposter syndrome, anyone?)

You don’t want to come off as a salesperson or aggressively annoying to clients. Approaching clients in this way only turns them off and gives them a reason to ignore your services. 

The best way to find freelance clients is by approaching clients with a common interest or goal. Having a common interest or goal is a good icebreaker to let your guard down and make a genuine connection. By bonding over a common outcome, you will feel more confident in sharing more about what you do and how you help your clients. This can help you minimize on of the biggest freelance challenges of finding clients.

Another good way to find clients is by volunteering your services within your network. If you have a network of college friends or colleagues, get the word out about your services. Offer to write a sample website, run a email marketing campaign, or rewrite a resume for a friend on a sliding scale. 

Your friends/family can be your first clients and testimonials. The more people know what you do and how amazing you are the more likely they are to refer your services and offer to pay you for your skills.

Here’s pro tips on how to start freelancing for free.

How do freelancers come up with freelance rates?

When it comes to charging by the hour or per project—or getting to the bottom of ‘what’s a freelance writer salary?’— plenty of freelancers struggle with determining how much to charge clients. It’s a common freelance challenge among many of us! Charging too much may make you feel as though clients can’t afford your rates. If you throw out a low quote for a freelance project, clients will think you are cheap and going to turn in low-quality work.

What’s the best solution to this freelance challenge of how to set freelance writer rates?

The best way to understand your freelance rates is by evaluating the time, skills, deadline, topic, and research required to complete the project. As a freelancer, your time and skills are valuable assets.

In my experience, if you charge too low for a project that takes up most of your time, you will be anxious to get it done. However, if you select a project that amplifies your skills and compensates you for your time, you will pleased with your work and commitment.

Charging by the hour or per project is at your own discretion as you grow as a freelancer. To help you determine the best options for you, here are five key questions to ask yourself before accepting a project:

1. Does this project cover my monthly expenses?
2. What is my bandwidth to take on this project?
3. Will this project require more time and energy than I have available?
4. Is this a project that fits with my skillset?
5. Does this project provide me with creative freedom and control?

How should freelancers handle bad freelance clients?

Not every client will be your best freelance client. (You might even find yourself in the middle of a freelancer scam!)

In fact, a common “con of freelancing” is dealing with “red flag clients” or those who exhibit “freelance client red flags.” There will be some clients who are a dream to work with from the initial phone consultation, project conception, invoicing, and finalizing the project details. 

Other clients will simply drive you up a wall over every detail of the project, have bad communication skills, last-minute changes, and late payments. (Been there!)

While working with “red-flag freelance clients” is a common freelancer struggle, the good news is that you don’t have to work with them again. As a freelancer, you have the authority to choose who you will or will not work with at your discretion. Be selective and work with people you like who respect you.

The best thing about being a freelancer is being in control of your income and knowing that  one rejection leads to the next client’s yes. Work with clients and projects that not only fit your skills and creative genius, but also respect your time and commitment to getting the job done right. That way, you can eliminate stressful freelancer problems or nip them in the bud before they steamroll your life.

Overcoming imposter syndrome 

As you begin to grow in your career, you will face many freelance obstacles—imposter syndrome is one of them. Feeling like an imposter is not that uncommon in the freelance community.

We often feel like imposters because we have high expectations for ourselves. We compare ourselves to our peers and begin to feel like we aren’t doing enough. While your feelings may present as valid in the moment. It’s important to understand that every freelancer’s journey is uniquely different, even yours. The important thing to remember is that you are your own person and your freelance journey is yours to create. 

Be mindful of negative thoughts and emotions. Learn to reward your small accomplishments frequently. Before you know it your imposter syndrome will be in your rearview mirror.

Don’t Let Freelance Challenges Sway You

Becoming a freelancer is a great career path for people of all ages and backgrounds. You can become a freelancer if you’re a retired teacher, college student, stay-at-home mom, or an entrepreneur looking to explore new opportunities. 

Freelancing is a great opportunity to supplement your income or start a new career. While there may be some freelance challenges along the way, plenty of freelancers have found great success by connecting with peers and learning from their mistakes.

Whether you become a freelancer to get your feet wet or explore a new career option, freelancing can be a great opportunity to learn something new and earn money as a side hustle.

Remember, your path is unique, and celebrating small victories can help silence the doubts. By tackling these challenges head-on, you can thrive in the world of freelancing and pave the way for a fulfilling career on your terms.

Frequently Asked Questions about Freelancer Problems

What are some pros and cons of freelancing?

Here are some of the pros and cons of freelance:

Pros:

• Unlimited income opportunities
• Variety of clients
• Networking opportunities
• Business ownership
• Freelancer Community
• Flexible scheduling
• Remote work

Cons:

• Competitive Market
• Quarterly taxes
• Steady clients
• Late payments

How to Find Your First Freelance Client?

The best way to land your first freelance client or secure your first freelance writing job is by working for a reduced price. You could also create samples for your website that show the type of work you can produce. When you’re first starting out without a strong reputation, landing your first client can a freelance challenge. 

By offering your freelance writing service at a more “ affordable” rate it could lead to a long-term client. One long-term client and a few referrals from them could turn into more revenue for you. Consider the bigger and long-term goals when you’re landing your first freelance client. If you’re thinking about ghostwriting in 2025 this guide can help.

Is Freelance Writing a Good Career For You?

Freelancing is a great way to learn a lot about yourself and work independently. Freelancing provides the opportunity for you to learn about different industries, cultures, and markets from around the world. The best part is that you get to offer your services and freelance skills from the comfort of your own home—or on the road.

There is a learning curve with freelancing. That’s why it’s wise to make sure you have a steady income to support your livelihood until you have a consistent stream of clients. Don’t let the threat of freelancer problems sway you. Freelancing is worth trying to see if it’s a good fit for you.