I am a prepress technician for a full-service commercial press (but not a trade/online printer), as well as being a graphic designer. This following exchange happens again and again in various forms...

Client: I can't print your proof. Can you please send me a print-ready proof?

Me: Our soft proofs are screen resolution for review/display only. We do not release press-ready printable files for proofing.

Client: But I need to be able to print it and make changes. Your file is locked. Can I have the password?

Me: We do not release press-ready printable files for proofing, and we do not share security information such as passwords used for document protection. I am happy to make any changes you need and proof it back to you. We do offer and recommend hard-copy proofing prior to print. The first hard-copy proof is free of charge. Would you like me to make your changes and email you an updated proof? Would you like a hard-copy proof for final approval before we print your brochure?

Client: Why can't you just give me the password? I am just trying to run my business. I need to be able to print this proof. I need to be able to make changes to your PDF before I print it. You are keeping me from running my business.

Me: I'm sorry, we don't release security information of any kind, and we don't provide press-ready printable files for proofing purposes. Please let me know what changes need to be made and I can get it done for you very quickly.

Client: I don't need changes now. I need to be able to change it in the future, and I need to be able to print it NOW. Every other printer that has designed something for me has given me a printable file. I plan to bring you tons of business and you are hurting my business by not providing me with the password.

So I send a printable file with a watermark...

Client: This is not acceptable. I cannot print this. It has a mark on it. Can you delete the mark and send me a high quality file? I need it right now. No other printer does this to me. 

Yes. I'm so sure that every other printer you work with provides you with a printable press-quality/press-ready file as a "Proof." Uh-huh.

At this point, this particular client chose to be verbally abusive and I had my boss take over the call. The client complained about me, told my boss that I was being uncooperative and hurting their business, etc. My boss pretty much repeated everything I had already said and reaffirmed our willingness to update and re-proof as needed. Th

Client: Fine! I'm going to get my designers to figure out how to unlock the file and fix the file for print. I'm NEVER going to work with you again.

But, wait... wasn't I your designer? And didn't you agree to a work estimate that included printing services with us? Hmmm. Good luck with that. I know you can get around the security with 3rd party software; but, I still sent you files that were exported at just 96dpi and don't include the bleed! 

Client: I am looking for someone to photograph my family reunion. I need 6 hours. Can you handle this?

Me: I'd be happy to! What date is your family reunion?

Client: My budget is [X]. How can I make a deposit?

Me: You'll be happy to know then that at my rates I only charge [Y] for event coverage. I can accept cash, cheque, or e-transfer. Do you have an email address I can send the contract to, or would it be easier to meet in person at a cafe?

Client: I will have you know that due to health reasons I need to do this through credit card in person. Can you do this?

Me: Unfortunately I cannot take credit card payments at this time, but I can accept cash, cheque, or e-transfer. Do you have an email address I can send the contract to?

Client: Good, I'll set you up with a merchant service then.

Red flags start flying up all over the place.

Client: This can easily be set up with your bank. I will give you my credit card and even pay the setup fees with your bank due to my health issues.

Oh yeah, this sounds scammy...

Me: Unfortunately I am unable to setup anything to take credit card payment, but if we can arrange an alternative I'd be happy to do the work. 

I never heard back from the client again. The date of the event came and went and nothing else came of it. Between his insistence on setting up something with my bank and him dodging my requests for an email address to send the contract to, I like to think I dodged a bullet.

I was working an internship for this small company that sells all kinds of cheap products made in China and the boss had me making advertising banners for their many websites. Most of it was typical stuff like promos for sales, holiday/seasonal-themed ones.

The client came over to check on me and I showed him what I had so far.

Client: Hmmm. No. I don't like any of these pictures. Why don't you just use Google?

Me: I did. This was the best I could find.

Client: Let me check.

He sat next to me and did a basic Google image search with no Creative Commons filter.

Client: Oh, hey, see? THIS one's better.

Me: Yeah but that might be copyrighted. If it didn't show up when I used the Creative Commons filter, that usually means it's copyrighted.

Client: Naw, I can usually tell whether an image is copyrighted or not. I'll check it.

He then stared at the image for a few seconds while I watched in disbelief.

Client: Nope! It's not copyrighted!

Thankfully I found a similar image that WAS okay to use because sorry but I am NOT risking my neck on your "magic vision."

I am a professional event manager. A few years ago, I was approached by a non-profit organization that wanted to erect a monument for all the victims of domestic violence. The three-headed organization had already organized a big event but decided that they were going to organize a concert to get the remainder of the money needed for the monument. They asked me about six months in advance if I was willing to be the stage manager for the concert. It was a worthy cause so I agreed. Then they invited me to a meeting.

Client: So, we are going to do a great concert, at this amazing venue. There are all kinds of artist that are willing to work with us for free, but they are all C-listers. We really want A-list artists. We also want a full crew of volunteers to do everything from sounds and lighting to stagehands, greeters, bar-staff, PA’s to the artists, promotions, etc. Besides that, we need full media coverage, and of course a great media campaign. We don’t really have anything yet, everything needs to be organized and designed. We have about six months to pull this together. Since we’ve already put in a lot of time in the last event, we decided that you get to do this one.

Me: You mean you want me to fully organize this massive event?

Client: No, no.

Me: Good. 

Client: We keep the last say in everything, you don’t get to make the final decisions. But other than that: yes.

Me: ...Okay, that is a lot of work for one person. If I would basically carry the sole responsibility for this and have my name tied to it, I would like to get some insight into the finances of the foundation. I'm sure you can understand that.

Client: NO! You just have to trust us! The money is none of your business!

Me: Okay. Then at least what is your budget for this?

Client: Pay? Oh no, we don't pay employees nor do we pay expenses for volunteers. Do you know how much of our own money we’ve already put into this fund? This must be a fun thing to do for a great cause! 

Me: ...

Client: You’re very serious, you shouldn’t be so serious!

Since I was sitting there with them, I didn’t really want to say something, so when I got home, I’d send them an e-mail saying that I was not interested in doing this project, but that I was still willing to work as a stage manager. They not-so-politely declined. 

A few months later, news trickled out that the director had been using the monument money to pay for his house renovations. So much for "you have to trust us!" 

Client: I’m not going to give you appropriate credits on my project.

Me: Why? I literally did everything in it.

Client: If I credited every person for their work, I wouldn’t look so cool.

Me: But crediting people means being honest.

Client: Now I feel conflicted.

I'm a web application developer. For over a year I worked productively with this client. We even made a follow-on contract.

One day, not even two months after the follow-on contract, my client suddenly came in for an escalation meeting, telling me he would need to forward my services to one of his business partners. He said that I wasn't performing as expected, which was the first time I heard that from him. We had meetings before in which he praised me and my results.

Me: Well that's a surprise. I'll have to think about it. 

Two days later, I had thought about it and told him I did not want to forward my services.

Client: Well I can see if we have another project you can work on. But if not, I will have to terminate our contract.

Three days later, he calls me:

Client: I'm calling to ask if you can reconsider forwarding your services to our business partner. We have something special planned for you there.  

He continued to tell shady details about how he wants an insider at his business partner to enable him to take them over. Basically I would be working for him as a spy. 

Me: Well I'm definitely not comfortable with that. 

Client: Don't tell anyone. This call and everything said falls under our NDA. Think about it, ok?

I did not hear from him for a week and continued doing my work according to our contract. One Monday I had an email in my inbox - written at Sunday evening - stating that he is sorry to tell me that he has to terminate our contract. The attached termination letter (I also received in print via mail two days later) was dated back at the date of the escalation meeting.

As our contract stated, that one side cannot terminate the contract without proper reasoning, I filed a suit. Three weeks went by with a lot of back and forth between my lawyer and his resulting in him withdrawing the termination.

During this process, even Even his lawyer said the client was difficult to work with

I used that lawsuit as my valid argumentation to fire the client shortly after and could enforce indemnity claims as well as other compensations.

Happy Ending. Always have a good contract.

Client: Hi. Do you do Photoshop? 

Me: Yes, I'm proficient with Photoshop. How can I help you? 

Client: I wanted to know if you do logo editing? 

Me: Logo editing? 

Client: Yes. I have a professionally-made logo, and I need it edited.

Me: I see... Well, what changes are you looking for? 

He sent me a low-res logo with a watermark.

Client: I need the semi-transparent thing over the main picture removed and the blurry edges made better.

Turns out, this client from hell had contracted a fellow artist - who is a friend of mine - to design a logo. The client bargained his way into paying 10% upfront instead of 50% like my friend usually charges, then after he was satisfied with the logo (which still had the watermark), he thought he'd be clever and tell my friend his work was inadequate and wouldn't pay the remainder. 

Unfortunately for him, the first person he tried was me. I immediately informed my friend, who warned the client from hell not to try using his work without paying. 

Client from hell ignored the warning, presumably found some other guy who was willing to turn a blind eye and help him (badly) remove the watermark, then used the blurry low-res image anyway. My friend tried lawyering up, but apparently, it wasn't worth it. Now he refuses to waver from his 50% upfront policy.

Client: I want you to get increase our customer base and get our existing customer to register for charity competitions.

Me: We can construct a content marketing plan to build authority and engage the audience, driving them to your website. We can try marketing to your existing audience to encourage sign-ups for your charity competitions and use the Charity fundraiser story to tell the story of the brand.

Client: Sounds great.

Me: Oh, I'll need access to your website to redesign it so that there are clear calls to action, sign up forms with eCommerce and design landing pages for various campaigns.

Client: You can't have access to the site until the developer has finished with it, at the end of the month.

Me: OK, why not direct them to add these changes while they are still under contract to complete the site.

Client: Will do.

Two months later:

Me: I haven't seen any updates on your site. Can I at least have access to your client database so we know who we're marketing the charity competition towards? 

Client: You will at the end of this month.

Me: Fine, but your first charity competition is now only several weeks away. We don't have much time to generate registrations AND the site still has no call to action or e-commerce registration forms so we can't grow the database.

Client: The web company owns the website. We will never have access and we can't afford to ask them for updates. There is no client database. We need charity registrations now or the company won't survive!

Me: What? why are you only telling me this now? No database? What have you been doing for the past year? Oh, and your third invoice payment is late again, will you be paying this now?

At this point, the client "lost my number" and stopped responding. Eventually:

Client: We don't want to work with you anymore and won't be paying you. We expect results immediately.

Me: But you signed a contract stating you understood content marketing results would be at least six months. If you are canceling fine, but there is a 30-day notice period. I need this in writing.

However, I'd noticed something else weird about his business at this point: he'd run his first charity event, and was funneling the charity money back into his business. I decided to bring this up: 

Me: I don't understand why you needed the charity event grossing 5,000 to keep the company afloat, are you not giving the money to the charity?

Client: We want to sue you for loss of earnings as the charity cost 10,000 to run and your content marketing isn't working fast enough.

Me: So you spent 10,000 with target earnings of 5,000 for yourself and passing it off as a charity event? You think something that will take six months to work should happen immediately and I'm to blame?

Client: Yes.

I worked at a hospital but did tech support on the side for many of the people that I worked with. One of these clients was a doctor that would still randomly bring up his high school football days in the most annoying braggadocious ways. As unpleasant as he was, he paid well, so I helped him numerous times.

One night I get a frantic text from him saying he needs immediate tech support:

Client: Can you fix a piece of paper if I give you a copy?

Me: Yeah, I can scan it in and photoshop it.  Is this for work?

Client: Not exactly.  Can you add text in?

Me: It depends...

Client: My wife asked me for a copy of the phone bill and I need a couple of numbers removed. *sends file*

It turns out that he had been having an affair and had been calling her on his cell phone a dozen or so times a day.  His phone bill was three pages long of small text and over half of it was phone calls to her. 

I was tempted to alter the file, charge him a hefty fee, and put in some watermarks stating this was an altered bill.  Instead, I took the high ground and ghosted him.

I ran into him recently and you'll be happy to know that his kid (from his ex) is "GREAT AT FOOTBALL."

I was helping an elderly business owner with marketing.

He seemed nice at first.

Client: I hear so many complaints from customers, I am immune to it by now. I feel like a surgeon, and after a while, it just feels like business as usual.

Me: I’m sorry to hear that. It’s important to get their complaints resolved as soon as possible these days, as customers provide feedback online.

Client: I don’t have time to figure out their concerns. I am providing useful products and services. This is how I run my business.

Soon after, I walked away after seeing countless complaints come in daily that weren’t even close to resolved.

A year later, I read in the newspaper that shortly after I left, there was a class action lawsuit against him for failing to provide basic levels of safety in his products and services. I am glad I was not involved.