Dealing With Difficult Clients: Red Flags, Approaches, and When To Say No

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Remember those 3 am text messages? The scope that changes faster than the midwestern weather? The inappropriate jokes that only one side finds funny? If the above examples sound familiar, then congratulations, you’re dealing with a bad client.

Here’s a fact:

A difficult client is rarely worth your time because you’re probably putting in unpaid hours to satisfy their ridiculous demands or paying the price of bad communication. Even if everything works properly, a toxic client burdens your mental health and could affect your other projects.

Therefore, as a freelancer, you should only accept clients who respect your expertise and understand your value.

Run While You Can: Red Flags in Your Client

I get it. It’s easier said than done, and good clients don’t fall from the sky. If you seem to be having bad luck with recent clients, next time, pay attention to these four red flags during your early interactions:

  • Unclarified goals and scope
  • Try to pressure you into lowering your price
  • Questioning your professionalism
  • Disrespecting your boundaries

Now, let’s take a look at each of these deeper

Unclarified Goals and Ambiguous Scope

Be cautious if a client can’t define their project scope. Test your water and see if they’re coachable. If you decide to move forward, create a clear scope description and include it in your contract as your protection.

Meanwhile, if all attempts to define the scope fail… Run!

“I’ve Seen People Getting It Done For Cheaper”

And I’ve had clients who pay twice as much and are as happy with the results.

Nothing else needs to be said. Feel free to run this guy through your Grant Cardone sales process. But in the end, if he can’t pay you a fair price, he doesn’t deserve your work.

Questioning Your Professionalism

Some clients think they know more than you do. Others act like you’re out there to scam them. While reassuring a prospect is part of your sales process, you should never put up with someone who doesn’t respect your professionalism. They can do the work themselves.

Disrespecting Your Boundaries

Clients aren’t god. Their payment doesn’t allow them to disturb your sleep, date nights, or me-time. A few good examples of client boundaries are

  • Clarified business hours
  • Minimum appointment notice (I require 48hrs ahead)
  • No group texts or private texting
  • No social media DMs or friend requests

If clients can’t respect these boundaries, they’re better off with someone else.

How to Deal With Difficult Clients: The Bottom Line

When working with any client, a freelancer’s bottom line is that the time and effort invested must be justifiable. If you feel like you’re “not paid enough for this shit,” start planning your exit.

Therefore, put all your clients on a scale. Does the effort you invest in them equal your compensation? Remember, here, compensation can be experience and knowledge you gain along the way. While I never vouch for unpaid work, I’ve also accepted lower rates for good opportunities that opened my eyes up to how higher-level projects work.

Setting Boundaries With Clients

Don’t be afraid. Setting boundaries with clients benefit both parties and often makes a project go much more efficiently.

On the one hand, boundaries with clients separate work and private time, allowing you to give them your undivided attention when you’re working.

On the other hand, boundaries can also look like a robust communication system that everyone sticks to — and we all know how good client communication makes a project go ten times faster and better.

How to Set Boundaries as a Freelancer

Freelancers and small business owners sometimes find it difficult to separate work and life. Therefore, start with your time management skills and incorporate time-tracking apps or calendar blocking to plan your day.

You should also create communication rules with clients (see my examples above), so nobody invades the other person’s space. A few additional boundaries include:

  • Clarify you don’t respond to or send emails on weekends
  • Specify if you celebrate any ethnic holidays
  • Outline your preferred communication methods during client onboarding
  • Block time out of your calendar for production (offline work time)
  • Similarly, create appointment windows instead of allowing people to book with you whenever.

Finishing a Project With a Client From Hell

Part of dealing with difficult clients is about finishing the project at hand even after you’ve realized you cannot work with this client any further. 

Why would you want to complete a project with a client from hell?

It allows you to finish things on a somewhat positive note. 

No matter how unreasonable and ridiculous they are, most clients wouldn’t publicly blast you if you’ve completed the project satisfactorily to a certain extent. They’d much rather just get their stuff and forget about you, and you’d much rather get paid and move on.

For new freelancers, having an extra portfolio item is beneficial.

We talked about how new freelancers sometimes feel like they don’t have many choices with clients. While you can create samples independently, having an additional completed real-life project in your portfolio could be beneficial.

It teaches you how to deal with difficult clients.

There is no better way to learn client relationship management than doing things hands-on. You’ll realize how much better and faster you react in a similar situation next time after completing a project with difficult clients.

Difficult doesn’t always mean unworkable.

Lots of things can cause a relationship to fall apart. But you can often resolve conflicts with a difficult client and maintain a good relationship. Don’t rush to termination unless you’ve thought the whole situation through!

How to Protect Yourself From Difficult Clients

We can’t guarantee we will never encounter a difficult client. Understanding how to protect yourself from them becomes critical to your business when it’s too late to bail.

Keep Your Emotions Aside

Difficult clients are worse than your toxic ex. They’ll use your normal emotional reactions to their abuse and bullying as ammo against you. Therefore, don’t allow them to gaslight you or elevate the situation. Keep your emotions aside and handle their bullshit as calmly as you can.

Document All Communications

Keep every communication documented. This goes back to what I talked about earlier on sticking to professional communications and avoiding private channels like text messages or verbal agreements.

Also: whenever your client changes the scope, get a written agreement and have them sign a separate contract or an amendment!

Stick to a Timeline

Regardless of the project, create a written to-do list and timeline with the client and stick to it. If you do installment payments, match said timeline with payment terms. This is your best protection and your grounds to take further action if a client refuses to pay and accuses you of incomplete work.

Create Clarity

Ask these questions:

  • Are we clear on what we just discussed?
  • Do you have anything to add?
  • Is there anything you’re concerned about?
  • Can we both agree on moving forward like this?

Cover your grounds with these questions so you leave no room for ambiguity and misinterpretation.

Client Not Paying: How to Ask For Late Payments

Chasing late invoices is never fun. And sometimes, you just have to give up because you know you’re not getting paid/getting ghosted, and the amount simply is not worth your effort to keep chasing.

However, I rarely give up chasing late payments — a dollar is a dollar. Below is a template I use to ask for late payments:

Dear [client],

I’d like to remind you that we haven’t received your payment for [Invoice No. XXX] that was due on [date]. If you had any difficulty in making a payment, please get in touch with us ASAP so we can work something out. Otherwise, your invoice will incur a [XX%] late fee each month of it being late per our agreement.

We look forward to receiving your payment.



The rule is simple: be direct but respectful. Check to see if something really did happen that made it impossible for them to pay you right now and offer alternative payment plans whenever possible.

Charging Late Fees on Invoices

You have every right to charge late fees on invoices as long as it is specified in the original contract and follows your state’s regulations. Here’s a great article from World Population Review on late fee laws by state as of 2022.

Getting the Court Involved: Is It Worth It?

Legal subscription services like LegalZoom and LegalShield help freelancers protect their rights without stepping into court. You can also consult your local Legal Aid for more affordable options.

Depending on the amount involved, sometimes it’s worth it to turn to a small claim court. But generally, most freelancers would agree that the time and money spent on hiring an attorney is way too big of a price to pay for a difficult client bailing out on one or two invoices.

In other words, make your judgment call!

How to Fire a Client: Would That Harm Your Business?

Never fire a client on impulse. Instead, always try to negotiate and resolve the conflict first. However, firing a toxic client is more beneficial than harmful to your business — that, I can guarantee.

Sometimes, firing a bad client is your last resort to damage control. Other times, you may both agree termination is the best option moving forward. Regardless, handle the situation calmly and with respect. Terminating a project with a client doesn’t mean you have to burn the bridges too.

There are plenty of ways to remain friends with a difficult client, even if your project doesn’t work out.

Sample Client Firing Letter

Below is a sample client firing letter. Pay attention that you should include additional terms based on services you’ve offered to avoid infringement or further issues.

Dear [Client name],

I am writing to inform you that [your name, or company name] will no longer be able to offer CLIENT [services being terminated]. According to the terms set out in our letter of engagement (dated x), our services will terminate as of [date].

This is a well-thought decision after our recent conversations and interactions, and I believe it’s the most beneficial for everyone involved. Regardless, I would like to take the opportunity to thank you for your business. I wish you success going forward.

[Additional terms on releasing any documents uploaded by the clients, and the ownership of any work that’s already created.]

Yours Sincerely,

[Your signature]

How To Deal With Difficult Clients: Final Words

Dealing with difficult clients is about remaining professional and respectful without sacrificing boundaries. Catch the red flags of bad clients as early as possible and respond accordingly. Set rules, workflows, and communication standards, and document everything. Protect yourself with late payment terms, and don’t be afraid to terminate a client when you need to.

Xiao DaCunha

With a deep passion for content creation and creative writing, Xiao Faria finds a strong sense of accomplishment in creating high-quality content that engages the audience and benefits optimization.

Throughout years of practice, Xiao has learned to communicate with the readers in the most efficient and effective way. Her experience as a visual artist has only aided her in creating refreshing and entertaining content.



Xiao DaCunha

With a deep passion for content creation and creative writing, Xiao Faria finds a strong sense of accomplishment in creating high-quality content that engages the audience and benefits optimization. Throughout years of practice, Xiao has learned to communicate with the readers in the most efficient and effective way. Her experience as a visual artist has only aided her in creating refreshing and entertaining content.

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