This guest post was contributed by Clients From Hell, a collection of the best stories about the worst parts of freelancing.

When you’re a freelancer, statements like this coming from clients are common:

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Like fairy tales, these anecdotes, filled with misery and monsters, have lessons in them. Here are a few of the most popular tales of horror from this week, and some lessons learned from them.

Story #1:

CLIENT: We want custom designs for all of the signage of our campus buildings. Both exterior and interior.

ME: Okay, that’s a couple hundred designs, but we can definitely take care of that. Right now, I can tell you we’re looking at a few weeks to complete. I’ll need a few days to figure out the details, work out a schedule, and then I’ll send you over an estimate and a quote for the down-payment.

CLIENT: Ah, yeah… we’re not really “down-payment” people.

ME: Ah, I see… we’re not really “work for free” people.

Lesson #1:

The submitter of this story did everything right; they outlined the scope of the proposed project, they gave a realistic estimate of the time it would take, and they had the good sense not to promise anything before ironing out the details.

Most importantly, they insisted on a down-payment. A down-payment is good practice for a variety of reasons. Besides ensuring the submitter gets paid something, it commits both them and their client to the project. When money is invested, a client is more inclined to invest the necessary time and resources as well.

Story #2:

I swear to God, prior to this conversation, I assumed that my client (like me!) was a native Italian.

CLIENT: I want this bit of the copy in Italian.

ME: I – okay, but can I ask why?

CLIENT: I like how it looks.

ME: Okay, but this is intended for an English-speaking audience, right? Won’t they –

CLIENT: Listen, it’s simple. Just put these sections in Italian and we’re done.

(A strange request, but I do as he asks.)

CLIENT: What’s this?

ME: It’s – I put those parts in Italian, like you asked.

CLIENT: Nah, I didn’t want any of this Spanish crap. I wanted it in Italian.

ME: What do you mean by “Italian?”

CLIENT: You know, slanted-like.

ME: You wanted it in Italics?

CLIENT: I don’t know what that is, but slant it up a notch or we’ll have a problem.

Lesson #2:

The submitter outlined their concerns about the client’s direction, which is always good practice. Freelancers are hired because their clients don’t have the time or talent to do something; saving their time and/or giving them the insight that comes from your talent are both things you should do.

The only other thing the submitter could have done is translated a small section and sent it for approval before translating the entirety of the copy. It’s a bit of a pedantic solution though, and one that’s tedious in practice. Still, “measure twice, cut once” is a time-and-stress-saving creed.

One thing the submitter can do to prevent something similar from happening again is to charge for the extra time. As stated, they outlined their concerns and they were disregarded. They provided translation services, and though those services turned out to be superfluous, the submitter still put in the time. By charging, the client is less likely to bulldoze the submitter in future instances. A discount on this time may lessen the sting of the hourly rate, in addition to giving the submitter a more defensible position if the client complains about the charge.

Story #3:

ME: The website will be ready no later than Wednesday, but since you’re on a deadline, I’ll make an effort to get it to you sooner.

CLIENT: Huh? So when will it be ready?

ME: Wednesday, but I’ll try for sooner.

CLIENT: Make up your mind. Wednesday or not?

ME: Wednesday.

CLIENT: Why did you say maybe sooner?

ME: I was just trying to be helpful. If I can build it sooner, I will.

CLIENT: I don’t get it.

ME: The site will be ready on Wednesday.

Lesson #3:

It’s always best to overestimate how long projects are going to take. Avoid putting the possibility of early delivery in the client’s head at all. Clients might push for it to get done sooner, but never, ever commit to a deadline that’s at the edge of possible. Too many things can go wrong and otherwise delay you.

It doesn’t matter what you actually said. If you don’t deliver on the possibility, the client will be disappointed, despite you not having done anything wrong. It’s a matter of managing expectations. If you simply deliver it early, sans promise, you have managed to exceed expectations and the client will be pleased.

Story #4:

CLIENT: The video you sent me has no audio – no music, no sound, no nothing! I can’t believe you messed this up, I was explicit about what I wanted.

ME: The video I sent has audio. I’m double-checking the file right now.

CLIENT: It’s not working. And I specifically told you I wanted music and everything. I don’t know how you can make such a stupid mistake. I mean, really.

ME: Are your speakers on?


ME: Hello? Are your speakers on and are you sure they’re –

CLIENT: Okay, I managed to fix it.

Lesson #4:

If you’ve been freelancing in your field for some time, it’s likely that you’ll start to recognize recurring problems or issues from clients. An excellent way to deal with these is to build a primer or FAQ and to attach it to your outgoing deliverables. This can include things like solutions to common problems, disclaimers that accompany unfinished products, or general context for the client.

For example, I have a template for my photography work filled with advice for models on how to prepare for shoots. In this submitter’s case, the eventual template would include things like “Make sure your speakers are on and no headphones are plugged in,” in addition to solutions to other similar issues I’m sure the submitter has had to deal with.

Unfortunately, you have no guarantee the client will read this – but it doesn’t hurt to provide it. Also, avoid rubbing a client’s nose in their mistake. Even if they act unprofessional up to that point, there’s no (good) reason you should do the same.

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  1. Ahmed

    Thank you for this great article!! even though i learnt these lessons from personal experience with a lot of hellish clients that would make you go crazy and commit suicide!
    But Good job, This would definitely help a lot of freelancers avoid these common mistakes.

  2. Jeni

    Thanks very much, made my afternoon to read these!

    We all have such situations – sometimes on the vendor side and sometimes embarrassingly also on the client side 😉

  3. Charlie

    Where are the Freelancers From Hell – or rather Freelancers From Jail?

    1. I describe what the software is to do. I give him a sample input and what the output would be. He quickly sends a tiny program and says it works and can I pay him. I enter in the input and sure enough the correct output appears. I try a different input and guess what? The same output appears. I look at the program and of course he is just writing the same output regardless of what the input is. I ask him about it and he offers to sell it to me for only 1/2 of the bid.

    LESSON: Act like you believe them even if you don’t. Pretend to be naive. Let them be crooks. See what they really like to do. But how do I have them arrested and put back into jail?

    2. “Pay me in PayPal or Western Union.” Can GURU search for “PayPal” and “Western Union” in messages? You will find the crooks.

    Lesson: Don’t be drawn into Organized Crime. You will regret it.

    Who has their own stories about the Freelancer From Jail?

  4. Charlie

    These are all examples of dumb people (or possibly even miscommunication.) It’s not against the law to be dumb. A good freelancer would see it as an opportunity to expand the project to include user training.


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