A while back my boss asked me to do a full-page magazine ad for an upcoming trade show. 

I mocked up the advert and supplied it to him for feedback and never heard back.

A couple of weeks passed and I forgot about it. The magazine landed in our office and I spotted the advert I thought I'd designed, but it was slightly different than what I did. 

Me: Er... What's this? It looks like our advert but it's been amended?

Manager: Yeah, the client's Head of Marketing convinced him to go with a freelancer for this based on your concept. They paid £800.

Me: But it barely looks any different.

Manager: (shrug)

The "freelancer" turned out to be a good friend of the Head of Marketing.

I worked as an external programmer for a graphic design agency; it was my first job for them.

They told me that it took two years to discuss the design with their client. I saw about 50 different pdf-files with slightly different colors and illustrations. I thought this meant the issue had been thoroughly discussed and was decided.

I've never been more wrong. Nothing was clear, everything was up for argument. Every time the client emailed us they asked for another minute change to the typography: kerning, line-height, anti-aliasing, font-smoothing. We actually discussed quarter-pixel values. Again: I was a programmer - this shouldn't have been my problem. But it was. 

After 10 weeks I finally finished my work. All I had to do was transfer the website to the server. Then I received another mail from the agency:

Agency: The client found out that the font we used will cost a license fee. They will not pay it. Use an GoogleFont instead.

Then the whole process started over from the beginning. 

Client: My designer is a guru. She doesn't need spot colors. She knows how to make her own.

Me: O_o

I've worked with many clients from hell over my career but the worst person I've ever worked with was a creative director from hell. 

This creative director was a nice enough man but had the biggest ego that I've ever worked with. If he didn't get his way, he made it his mission to work against the person who challenged him.

It all started to go downhill when we had a design meeting about some design changes to the site. He told us how we should all to be honest and there are no bad opinions. He rolled out the changes for the top nav to use the main brand yellow as the background and the nav items as white. I pointed out that a lot of the audience for the site are seniors and having that low of contrast will make it hard for them to read. That was all he needed to hurt his ego enough to dislike me. 

Over the next couple of months I had to work with a Creative Director actively trying to work against me. He would do things like:

• Get mad at me about very small details when I didn't follow the style guide but never actually send me the style guide. When I would mention that I don't have the style guide he would say "You don't really need it, you should understand our style by now" 
• Get me do to ads with no direction or content, just a vague idea then get mad at me when it wasn't exactly what he wanted. Then he would get another designer to redo it and tell everybody in the design meetings how much better the other designer's version was.
• Create make work projects for me to design banner ads that would never end up getting used then make it look like I never did any work because nothing I did was ever used.

In the end I decided to talk to the HR department about it and next thing I knew he decided that the marketing department was too big and it needed to downsize. I was the only person let go. 

But on the plus side, I got a massive severance package from the company and it allowed me to take time off and only apply for jobs that I really wanted to do rather then jump into another job just to pay rent. I ended up getting my dream job where I have been ever since.

Client: Why is my French version website not completed along with the English website?

Me: What French version?

Client: It's in the proposal and initial brief we provided!

I went back and checked the documents. 

Me: I can't see it anywhere. Also, you asked us to re-do this proposal 6 times to meet your requirements and a French version never came up. 

Client: Are you calling me a liar? I want the French website at no additional cost.

Me: Ok, I can design these email campaigns for you. What format do you need?

Client: That’s great! Go ahead and design in a format we can copy and paste from Outlook.

Me: Here are the emails in Outlook, I’ve also included HTML files as most email systems support this. I’m not familiar with the system you’re using so please let me know if you need them in a different format.

Client: These are perfect! Thank you!

Radio silence for a few weeks, and then. 

Client: The format isn’t compatible, this isn’t going to work, don’t bother fixing it. 

Me: I tried to accommodate based on the information I had. What system are you working with? Can I try putting it in directly? 

No response. Don't tell me I did something wrong if it's because you didn't give me enough information and won't let me try to fix it. 

Client: I haven't received any emails since the website went live yesterday, I told you to be careful with our emails when migrating the site to the new platform and now my office is at a standstill!

Me: let me look into it.

I forwarded the ticket to my IT guy who gets in touch with his IT guy to resolve the matter. A few minutes later the client called back.

Client: Don't worry about it. My PC was just running slow because I've been out of the office for a day

Bit of a different context, but I thought the sentiment would be appreciated.

While I was in law school, over the summer I interned at a state child welfare office. Whenever a caseworker needed a copy of a court order, they would send an email to my boss, who would forward it to me. I would write down the case number and order date, and go down four floors to the clerk's office in the basement. I'd give them the case number and order date, they would pull the order, make a copy of it, and give me the copy. I would then go back up four floors to our office and scan the copy of the order to my computer, and email it to my boss who would forward it to the caseworker. 

I had never fully appreciated the futility of bureaucracy until that moment.

During a meeting with a relatively new client, I noticed the left side of my face was starting to go numb. I mentioned this during the meeting, and terrified that I may have been having a stroke I ended up going to urgent care afterward. It turned out to be Bell's Palsy, which is annoying but mostly harmless and usually heals within weeks or months. I told the client about this the next day and got on with my work.

Two weeks later, the client asked me if I'd completed work on something I didn't recall discussing with her at all. I asked her when she'd asked me to do this as I had no emails or records about it, and she said she'd brought it up during the meeting two weeks earlier.

Me: You mean the meeting where I thought I was having a stroke?

Client: Yes.

Me: I wasn't really mentally present, as I'm sure you can understand, and you've not mentioned it to me since.

Client: When I ask you to do something I expect to see it done.

Me: I understand that, but you asked me to do this during a meeting when I was having a stroke.

Client: That's not a good enough excuse. If you'd been working with me longer I might understand, but you've only been on this project a few weeks.

Me: How long do I have to have been working with you for it to be okay for me to have a stroke during a meeting?

Shockingly, the client didn't have an answer. I ended up leaving the project not long after that.