Some Experts Share Their Worst Freelance Experiences

The freelance world can be a wonderful place for earning some extra income. But, not everyone has been treated like a princess or prince by every client. That is why I asked fellow freelancers from different industries what their most disastrous freelance experience was.

Here are some experts’ thoughts on their worst freelance experiences.

Takeaways
1. Learn from the Mistakes: Gain valuable insights from experienced freelancers who have faced challenges and learn how to avoid common pitfalls.
2. Client Management: Understand the importance of effective client communication and management to navigate difficult situations professionally.
3. Setting Boundaries: Discover the significance of setting clear boundaries and managing client expectations to maintain a healthy work relationship.
4. Handling Payment Issues: Explore strategies to protect yourself from non-paying clients and ensure a fair compensation for your freelance work.
5. Coping with Difficult Clients: Find out how to handle difficult clients while maintaining professionalism and delivering quality work.
6. Building Resilience: Embrace the challenges of freelancing and learn how to stay resilient and positive throughout your freelance journey.
7. Lessons from Other Freelancers: Benefit from real-life stories of freelancers who have encountered tough situations and emerged stronger and wiser.
8. Leveraging Client Feedback: Understand the importance of client feedback and how it can be used to improve your freelance business and skills.
9. Embracing Freelancing Adventures: Embrace the ups and downs of freelancing as part of an exciting and fulfilling career choice.
10. Continuous Learning: Recognize the value of continuous learning and self-improvement to grow as a freelancer and overcome challenges more effectively.

#1 Expert Freelance Experience 

When I was first starting out, I took on a project I wasn’t qualified for, and I didn’t know how to tell the client that. So I spent a month working on it and trying to figure it out, and at some point, along the way, I had to admit that it wasn’t going to happen. The client was pissed, and they were right to be—I wasted their time and mine. And then they didn’t pay me for the month’s worth of work.

Lesson Learned: Know your limits, and don’t take on projects you can’t complete.

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#2 Expert Freelance Experience 

I worked on a [X] project that took months to complete. They kept coming back and asking for changes without paying more money, which would have been okay if they had given me a heads up, but they didn’t. I was just supposed to magically know that the changes they were making had cost implications.

Lesson Learned: Always get a scope of work in writing before you start the project.

#3 Expert Freelance Experience 

I’ll never forget the time I had to write a blog post on how to remove ants from your home. For the life of me, I couldn’t figure out why they needed me to do it—it was just a listicle, like “put down sugar water,” “use vinegar,” and “cross your fingers.” Being the diligent person I am, I emailed them back with a list of questions (“Do you want me to include any specific products? Do you want me to tell people to call an exterminator?”) and then waited for a reply.

The client didn’t respond for a few days, so I assumed they were just busy. And then I got an email that said, “It’s been two weeks since we hired you and we still don’t have our content. Did you do it?”

They hadn’t responded to my questions! They hadn’t even read my emails! How could they possibly expect me to do their work when they hadn’t told me what they wanted? It was infuriating.

Lesson Learned: Get all of your details in writing upfront. And if you’re hiring someone, make sure that you actually read their emails!

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#4 Expert Freelance Experience 

During my first time freelancing, someone asked me to write some emails for them. I was young, and I didn’t know what I was doing, so I took the job.

I worked hard on the emails and put a lot of thought into them. But when I sent them over to the client, they just said “thanks.” No feedback, no questions, nothing.

I had no idea if I did a good job or not—so I just assumed my work wasn’t good enough. It took a while before I could convince myself that it was OK to try freelancing again.

Lesson Learned: The clients who give me feedback are the ones who help me become a better writer—and they’re often the ones who keep working with me in the long run!

#5 Expert Freelance Experience 

Some clients are just not great people. They may be rude, they may not pay on time (or at all), or they may lie to you and use your work without paying you. This can be extremely frustrating, but it’s important to remember that this happens to everyone! Even if it feels like the end of the world at first when a client does this to you, know that it gets easier—and that these clients are rare!

Lesson Learned: This kind of thing happens to everyone! It’s rarely personal—just business!

#5 Expert Freelance Experience 

I mostly work with one client. She was an editor, so I assumed she would be great to work with. And she was—at first. But then she started asking for changes and revisions that were totally unnecessary—like changing the wording of every sentence in every paragraph or adding in a bunch of extra content that wasn’t needed. I would try to explain why the change wasn’t necessary, but she didn’t listen to me and wanted it done anyway. It made my work time triple and my pay halved!

Lesson learned: Learn from my mistakes! Do not assume that because your client used to be an editor, they’ll take your advice as a writer. And don’t be fooled into thinking that all good writers are good editors. It’s just not true.

Worried about getting banned from Upwork? Learn why it’s not the end of the world in our article on Why You Shouldn’t Be Afraid of Upwork’s Permanent Ban. Gain insights on bouncing back and thriving in the freelance marketplace.

#5 Expert Freelance Experience 

I’ve had some pretty terrible experiences as a freelancer, but I’d say the worst was probably the time I worked with a client who kept changing her mind on what she wanted every two weeks. It took me six months to finish the project because every time I got somewhere close to making progress, she’d send me a new version of the brief that was totally different from the last one.

Lesson Learned: This is one of those things that happens less and less as you get more experienced: you learn how to set your client expectations up front and make sure you get a clear picture of what exactly they’re looking for before you start working.

#8 Expert Freelance Experience 

Oh, and another time, I got assigned to work on an article that was due in three hours without having been told that the deadline was so soon! The client didn’t get their article until 5 PM (an hour after the deadline), and they sent me a message at 5:01 AM letting me know that they were going to be trying someone else next time.

Lesson Learned: Be sure to check your email and notifications regularly for messages from clients.

#9 Expert Freelance Experience 

Freelancing has been a mixed bag for me. Some days, I’ve had incredible experiences with some of the most talented people in my industry. Other times, I’ve been burned by clients who didn’t understand the complexity of my line of work, or who tried to undercut me on price. But overall, I’ve enjoyed it and grown tremendously as a professional.

Lesson learned: When you’re working with clients, make sure that you’re both on the same page about the scope of your project. That way, you can avoid surprises when it comes to payment, and they’ll know exactly what they’re getting from you!

#10 Expert Freelance Experience 

The first time it happened, I was working on my first major project for a company in the United States, and it was supposed to be a long-term position. I worked hard and did everything they asked me to do for about two weeks before they stopped giving me any work. It took them almost 3 months to pay me, and by that time I had already taken other projects to replace the income from that one.

Lesson Learned: Even if you are a new freelancer, keep your standards high. Don’t let anyone make you compromise your principles or work more than is reasonable.

Even if it’s not your fault, don’t be afraid to impose penalties on late payments if that’s part of your contract. You need to be compensated for your time and energy, whether the client is happy with your work or not.

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#11 Expert Freelance Experience 

Some of the worst freelance experiences I’ve had were when a client asked me to research a topic, then refused to pay me for it. There’s a lot of time and effort that goes into researching topics, and many clients do not understand that.

Lesson learned: If a client asks you to research a topic before writing any content, make sure they agree to pay you for your time.

#12 Expert Freelance Experience 

My worst experience was with a client who kept pushing back the deadline on what should have been a simple project. When it was done, they asked for rewrites, but then said they didn’t like it and wanted their money back. They’d given me very little guidance in terms of style or tone, so I wasn’t sure how to handle these requests. The end result was that I spent more than five times longer on the piece than I originally thought it would take me, which ended up costing me thousands of dollars in lost time and opportunities.

Lesson Learned: Don’t be afraid to ask questions when you need more information from your client and don’t be afraid to decline unreasonable requests. Make sure you’re clear about your boundaries as a writer (and as a person).

#13 Expert Freelance Experience 

A client whose projects were constantly changing. This one was also very frustrating because it wasn’t my fault—the client just kept coming up with new ideas, which meant I had to change course all the time. It took me twice as long to finish each piece because I kept having to go back and check-in with them on what they wanted next. This cost me hours of billable time that could have been spent doing something else!

Lesson Learned: The lesson I learned from this experience is that when you’re a writer, time is your most valuable asset. Anything you can do to save time will help you work smarter and make more money in the long run.

#14 Expert Freelance Experience 

Another time, I had this one client who took forever to pay me, even though we had agreed on a deadline for when she’d pay. I sent her an invoice that detailed the amount we’d agreed she’d pay for my work, and she just ignored it for weeks at a time without saying anything. Then she’d send me an email saying something like “oh, right…you need to be paid.” And then another couple of weeks would go by before I heard from her again. It was really frustrating!

Lesson Learned: The lesson I learned from this experience is that it’s really important to make sure you’re clear about payment expectations with any clients you take on—not just in terms of what the price will be, but also when they’ll need to pay you. It’s always best to be as direct as possible about these things.

#15 Expert Freelance Experience 

I once worked with a client who didn’t trust me to do a good job and kept micromanaging me. He would tell me what to write, and then he would have his girlfriend or his mom look it over and tell him if she thought it was good enough or not.

I don’t know about you, but when I’m being commissioned to write something, I like to be able to do my own thing. It’s just not very fulfilling when someone else is looking over your shoulder and telling you what you’re doing wrong the whole time.

Lesson Learned: If you hire someone to give you create content, let them be creative.

#16 Expert Freelance Experience 

For me, it’s when clients don’t pay me on time. Working with people who don’t pay on time is pretty much the worst because you end up doing twice the work for half the pay. First, you have to do all the work and then you have to track them down and get paid, which takes extra time and effort.

Lesson Learned: Keep your eyes out for red flags like this in a potential client, because these things will end up costing you WAY more in the long run than it’s worth.

#17 Expert Freelance Experience 

One client was very demanding – they asked me to do the work I had done that day, but in a different way. This was a lot of work as well; I think this happened three or four times.

Lesson Learned: I learned to be more patient and understanding, even when a client is being very demanding. The client was under a lot of pressure from their boss, so they were acting out and taking their frustration out on me. I had to keep reminding myself that they weren’t just being difficult for the sake of being difficult and that the situation was probably much more complicated than it appeared.

#18 Expert Freelance Experience 

I worked for a client who was super picky and always wanted more content than we agreed upon—but this wasn’t too much of a problem because they paid well and on time. The problem is that it turns out they had a bunch of other writers working at the same time on the same project. So I spent an entire week writing a huge amount of content… only to have them decide it didn’t work for them after all.

Lesson Learned: It’s not enough to have one or two very loyal clients; you need to keep your eye out for new opportunities, too. If this client dried up, I would have been in trouble.

#19 Expert Freelance Experience 

I got screwed out of $10,000 by someone who said they’d hire me for a pretty big project and then ghosted me after I turned over all the work.

Lesson learned: Be wary of clients who ask for too much upfront. Don’t let your fear of missing out on an opportunity blind you to red flags that show up in their communication practices. 

Freelancing isn’t all smooth sailing, but it’s an exciting journey! Discover the truth about freelancing experiences in our article on Freelancing Isn’t Always Great, But It’s Always a Good Time. Embrace the ups and downs, and turn your freelance career into an adventure worth pursuing!

#20 Expert Freelance Experience 

I once signed a contract without reading it thoroughly (first mistake), and when I did go back to review it, I saw that it wasn’t very favorable to me. It was very vague, which meant they could have me working on the project for months—without getting paid more than what we agreed upon upfront. They also wanted to own all of my work after the project was over, meaning I couldn’t use the content I created for them ever again.

Lesson Learned: Protecting your content is important. Set yourself up for success by making sure that whatever you create is legally yours from the get-go.

#21 Expert Freelance Experience  

I once had a client who sent me a project that had no instructions and was due the next day. I did my best to get it done, but there were some gaps. When I gave it back to him, he lost his mind. He sent an email after email telling me how much he hated the work, and how unprofessional it was. And then he stopped paying me for the other work that I’d submitted up to that point (which had been a lot).

Lesson: Don’t do rush projects for clients who don’t communicate well, or at all!

Further Reading

5 Freelancers Share Their Worst Client Horror Stories: Dive into the nightmarish experiences some freelancers faced with their clients, and learn valuable lessons from their stories.

How to Recognize a Bad Freelancer Through Client Experience: Discover the signs that indicate you might be dealing with a subpar freelancer based on real client experiences.

Clients From Hell: Freelancers Share Their Stories: Read hilarious and horrifying anecdotes from freelancers about their encounters with difficult and unreasonable clients.

People Also Ask

What Do You Think Is The Most Important Thing A Freelancer Can Do To Make Sure They’re Doing Their Job Well?

I think it’s really important to get to know your client before agreeing to take on a project. I’ve found that making sure we’re on the same page from the start helps us work through challenges and meet deadlines much more seamlessly.

What’s Your Worst Freelance Experience?

My worst freelance experience was when I had a client who was extremely difficult to contact and would often miss deadlines for approval or go dark for days at a time. This made it really hard to work with them and ultimately led me to stop working with them.

How Many Clients Do You Have At A Time?

I typically take on 3-4 clients at once, so that I can balance my workload effectively and allocate enough time to each of them. I like having 2-5 projects going on at once because it gives me the ability to take breaks between projects and keep my work fresh.

What Mistakes Should Freelancers Avoid?

Freelancers should try not to overcommit or miss deadlines because both of those things can damage their reputation as a freelancer

How Do I Avoid Scope Creep?

It’s a good idea when you’re first starting out to have a contract with your client that lays out what you are and are not responsible for during the project. That way, you don’t get stuck doing extra work for free or having to charge extra money because your client has asked for more than was originally agreed upon.

How Can I Make Sure I Get Paid?

It’s a good idea to always get everything in writing. Make sure you have the payment amount, due date, and method of payment in writing before you start any project. It’s also recommended that you ask for a deposit of at least 30% before starting any work. That way, if your client doesn’t pay you, at least they’ve compensated you somewhat.

Did You Ever Have A Client That Didn’t Pay You?

Unfortunately, yes. It’s just part of the gig. Hopefully, you can collect that money by taking legal action, or at least make sure your fellow freelancers are aware of the situation so they don’t get taken advantage of by this delinquent client.

What Was The Most Challenging Part About Working With Clients?

Maintaining a good relationship with the client and communicating clearly can be difficult. But most importantly, it’s about setting clear expectations for deliverables, deadlines, and total fees from the beginning. If you’re clear about what’s expected of each other from the very first contact, then it becomes easier to manage any issues that arise in the process.

What Are Some Of Your Worst Freelance Experiences?

I’ve had trouble getting paid for my work, but I try to make sure that doesn’t happen very often. I also just really hate it when a client is rude or tries to argue with me about the work I’ve done.

What Do You Do To Stay Motivated When You’re Struggling?

I take a day off. I have a ritual where I get up late, eat a big breakfast (usually an omelet with turkey bacon), spend some time watching comedy specials on Netflix, then go for a workout followed by yoga. The next morning, I’m usually feeling much better!

I Was Ghosted By A Client. What Do I Do?

We’ve been there. It’s not fun, and it’s definitely not fair. Working in the freelancing world is all about building your reputation and connections, so when a client ghosts you, it can feel like a huge hit to your professional image.

Unfortunately, there’s not much you can do—other than make sure that you’re thorough in how you document your work with each client and reach out to them if you don’t hear back after a reasonable amount of time (after which point you should assume that they just aren’t going to answer). Make sure you get as many details about a project before starting as possible and plan on following up frequently until the project is complete.

A Client Wants Me To Sign An NDA. Should I?

NDAs can be tricky (which is why they exist). We recommend reading through one line by line before signing anything, and asking your lawyer for clarification if something isn’t clear.