The Ugly Truth About Freelancing: How To Deal With Difficult Clients


From energy vampires to late payers, nit-pickers, lower-ballers, passive-aggressive commenters, and impossible expectation-ers…

When it comes to dealing with “difficult clients”… How do you set and keep boundaries?

Hey Posse! What’s up? It’s Alex. 

If you’re new to the crew, welcome! 

This blog is here to bring you the latest in marketing, copywriting, and freelancing, so for more tutorials like this one, go ahead and subscribe to my newsletter. 

Now I’m super excited about today’s article because I feel like this is a topic that ALL my fellow freelancers and creative entrepreneurs can relate to…

No matter your niche or industry, when you work in a client-based business, you’re bound to stumble across one or two (or three or four …) clients that push your boundaries AND your buttons. 

And trust me, I have been there! After a decade of running my own freelance copywriting business, I have dealt with my fair share of difficult clients and boundary-pushers. 

And in the beginning of my career, I did what most new freelancers do… I let my clients call the shots AND completely lost sight of my so-called boundaries. I lowered my prices to unreasonable rates, I let clients call me on weekends, I’d work at all hours of the day, and I’d agree to the most ridiculous turnaround time without a second thought.

But over the years, I did a lot of mindset work to shift that dynamic, but there was one mindset change in particular that shifted EVERYTHING for me. And I’ll tell you all about that at the end of this blog post… 

First, what I really want to talk about is HOW you can actually stand your ground as a freelancer and hold your boundaries with difficult clients, WHAT to do when that doesn’t work. And most importantly, I’m going to give you 5 super tactful ways to FIRE a client on GOOD TERMS without burning professional bridges or risking your reputation. 

So let’s get right into it…

The Most Important Skill You’ll Ever Learn

As a freelancer, you’re constantly learning and reviving your skills. I mean, you kind of need to if you want to stay in demand and on top of industry trends… But there’s one skill in particular that most freelancers never learn.

And that’s why they struggle to hold boundaries and find it impossible to say goodbye to bad apple clients…

The skill is this: Learning how to have difficult conversations. 

Here’s the thing… when you’re a freelancer or business owner—you HAVE to learn this skill. Whether it’s talking about money, setting proper expectations, or communicating a boundary that has been crossed…

People hardly ever see eye-to-eye on everything. And people definitely aren’t mind-readers. This means that having difficult conversations is often the only way to truly grow and thrive in your business. 

One of my favorite quotes of all time is by Tim Ferriss..

A person’s success in life can be measured by the number of uncomfortable conversations he or she is willing to have.

After a decade in business, I can tell you no truer words have ever been spoken. And I promise that 9 times outta 10, what starts as an uncomfortable convo, ends as a giant RELIEF and a new perspective. 

So buckle up, because it’s time to get comfy with being uncomfy!

When To Stay & When To Go

Okay, so now that you’re comfortable with getting uncomfortable… Let’s talk about how to actually approach and handle difficult clients.

Just because you’re willing to have difficult conversations, doesn’t mean you need to go around and fire every single client that pushes your boundaries.

Because remember: Your clients aren’t perfect!

Nobody is perfect! And most clients simply don’t realize they’re being difficult unless you TELL THEM.⁠ Trust me on this one… because I’ve been on BOTH sides of this situation—as the fed-up freelancer AND the “imperfect client”. 

Now here’s the thing you need to remember about “difficult clients.” When you’re an entrepreneur hiring a team or putting something out into the world with your face and name on it, it can be really scary (and difficult) to LET GO of all the things you used to do yourself…

Which can sometimes—and completely unknowingly to the client—lead to unwanted micromanaging, nit-picking, or asking for a million revisions.

It’s not always that they don’t appreciate your value and talent… sometimes it’s simply that they’re having a hard time letting go and trusting the process. 

So, before you take the harsh approach and start firing what could turn out to be a great working relationship, instead try the empathetic approach. And remember that your client might just be feeling overwhelmed or scared. And that maybe… just maybe… all you need is one candid conversion to resolve these issues. 

So with all that said… how do you really know when you should fire a client or when to stick around and try to make things work?⁠

Here are a few things to consider before you decide to say goodbye:

⁣⁣⁠1. Reassess how important this client is to you. ⁠

So if you love working with a client, and you see a good future working relationship with them, then the temporary uncomfortableness of a candid conversation will likely be WELL worth it!⁠

Really great clients are few and far between, so if you think you have a good one, then it’s silly to throw in the towel over a misunderstanding or unclear boundary.

2. Set clear expectations from the start with a contract

I cannot stress this enough—always enter into your client relationships with a contract or statement of work that clearly maps out expectations and boundaries. This way there’s never a question and any misunderstandings can be cleared up quickly and painlessly. 

And if you’re kicking yourself because you’ve never once drafted a contract for your clients… remember: it’s never too late to start! 

Even if you’ve been working with a client for years… you could simply approach them and say:

As my business grows, I have realized that I need to start keeping better documentation of my client’s needs and expectations – so I’ve drafted up this contract to make sure we’re always on the same page. Could you look it over and come back to me with any questions or revisions?”

3. Stand your ground 

Don’t be afraid to push back and politely stand your ground. Be ready to clearly explain:

  • What the problem is
  • How it’s impacting your work, their business, or others
  • What needs to change going forward

Try to keep it as factual and unemotional as possible (I know! This is a hard one for us empaths!) Stick to using facts, statistics, and specific examples if you have them. 

And remember, no matter what happens, in the end, your client will respect you more for having the courage to stand up for yourself and hold your ground. 

4. Ask yourself, can this situation be turned around, or is the relationship flat out toxic?

If it’s toxic… then you need to get out… Fast.⁠⁣⁣⁠⁠ You’re not obligated to stay if it’s just not working.

And that leads us to…

5 Tactful Ways To Fire A Client 

Sometimes, despite your best efforts and most candid conversations… the best solution will be to say goodbye.

Firing a client is probably the right thing to do, if…

  • They deplete your energy, your creativity, and worst of all… your self-worth.⁠
  • ⁠They keep you so busy that you can’t work with other, potentially better paying (& easier to manage) clients. 
  • ⁠They’re toxic, impossible to manage, constantly demanding additional work, don’t respect your boundaries or time, are overcritical & negative.⁠
  • You’ve been through the four “Should I stay?” questions and feel confident it’s best to move on

So once you’ve made the decision that it is, in fact, in your best interest to fire your client… here are 5 super tactful and professional ways you can end the relationship without guilt, shame, or resentment (for either party!)⁠

#1 – “I am taking my business in a different direction.” 

This is a great way to redirect the blow and make it feel less personal to the client. Say you’re firing a client that you write content for and you’re no longer offering that service anymore, then it’s not necessarily your client’s fault… it’s the business direction’s fault! 

#2 – “This is outside the scope of what I offer.” 

Sometimes clients will give you work that’s outside of what you specialize in or want to do. This is a perfect example of where a contract or statement of work would come in handy. But even if you don’t have one, remember that it’s your business and you get to decide what you say yes or no to. 

#3 – “I don’t believe I’m the best person to help you with this.

Giving a reason like this lessens the blow because it’s your way of saying “It’s not you, it’s me.” There’s no point in wasting your or their time if you can’t sufficiently meet their expectations. This will allow them to find someone who is a better fit for their needs. And you can find someone that’s a better fit for you too. 

#4 – “This isn’t something I’m able to help you with, but I know someone who can!

Suggesting a different copywriter, freelancer, or agency is something they would likely appreciate! This is one of my favourite ones because it really comes across as non-personal and even helpful. Most business owners hate searching for a freelancer that meets their expectations—because let’s face it—they are hard to find! 

#5 – “I appreciate you thinking of me, but I don’t feel we’re a fit.

This is a good one for the clients that you just don’t see eye-to-eye with. Remember, you don’t owe them an explanation beyond this, but honesty is always the best policy! Telling them exactly what didn’t work for you might help them when hiring their next freelancer!

Alrighty now for the big mindset shift I promised you…

The Mindset Shift That Changed EVERYTHING For Me

Grab a pen and paper, cuz this is a juicy one and you’ll def want to write this down…

I’m a business owner and have full control over which clients I decide to work with.” 

Now, this is a mindset shift that soooooo incredibly difficult to make—ESPECIALLY as a beginner. ⁠⁣⁣⁠⁣⁠⁠Because as a fresh-on-the-scene freelancer you want to make a good impression, do a great job, get referrals, and maybe even a testimonial…⁠⁣⁣⁠⁠

So you tend to naturally fall into the employee/employer way of thinking. 

⁣⁠⁣⁣But allow me to remind you of something…⁠⁣⁣⁠⁠

YOU are your own boss! Your clients are NOT your boss—they are your clients!

You enter into every client relationship to be MUTUALLY beneficial for both parties… and remember that at the end of the day… You are the expert. And they need you! 

Alright guys, leave me a comment up below if you found this helpful.

Until next time, I’m Alex.

Ciao for now! 

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3 Comments. Leave new

  • Jerikho Jordan
    October 25, 2021 7:52 am

    This is a good read! I’m new at this and am currently learning the ropes to freelance writing. One of the things I fear is having to deal with challenging clients. And that is something bound to happen. Thanks for sharing. This helps a lot.


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