I was working with an older client putting together a pamphlet. They gave me zero input on design other than giving me a number of photos that were 100 kb or less that I begrudgingly put into a gallery wall. Otherwise, I gathered a number of free stock photos that vaguely suited their business. They matched thematically and looked good in the design.

Turns out, stock photos are catnip for boomers. Every revision I've made since (we're now in round 4) has been moving these stock photos and replacing them with other sub-200 kb photos they discovered on an ancient hard drive. 

Clothing designers come to me to engineer their ideas for mass production. This is one of the great visionaries I work with: 

Client: The sample was too big so I took it to a tailor to slim down. Just follow the sample for the final draft. 

Me: Ok, but when I compare your sample it is actually larger than the pattern it was built from. I think your fabric is growing and that's a problem. 

Client: You need to make it smaller otherwise the pattern is not useable. I can't pay for this type of work. 

Me: But the pattern is already smaller. 

Client: I have invested so much money into this project and I am really expecting this to be as I need it. I need to start making money, this project needs to launch... (rant continues about money woes, other issues not related to my services and the hardship of being a startup) 

Me: Umm ok. I'll make it match the sample. 

I ended up making it bigger and thoroughly documented this fiasco. 

This happened in the 1990s. The company decided to purchase an AS400 minicomputer and some very expensive databases to run on it. Before we could start, a conference room had to be converted to a raised floor datacenter. (We had been using a utility closet for our file servers.)

The local building inspector was unsure of his expertise, so he would have to borrow an inspector from the state. Then, IBM had to send a technician to install the AS400. Then, IT sys admin had to be trained or hired, software installed, backups set up, employees trained, custom reports completed. The consultants hired by the company said 2 years to complete. At the big meeting, the boss said 6 weeks and walked out of the room as the department managers started yelling and the IT group just sat with our mouths open.

In six months time, we had enough of the system up and running and one (1!) employee trained to do data entry. The boss watched her fill out a screen and said, "See! I knew you could do it." Any respect I had for the boss disintegrated in that moment.

In one month shy of 2 years, the last custom report was completed and approved. Not bad.

I was asked to write some copy for an Instagram BIO

Me: here you go, what do you think of this?

Client: Could you make it longer?

Me: Sorry, Instagram limits you to 150 characters

Client: Couldn't you make the box bigger?

Me: No, sorry

Client: Could you use this instead then

Gives me poorly written content that is over 150 characters

Me: Sorry, that is over 150 characters

Client: Could you remove the spaces?

Me: ...

We just published a new issue of our magazine, which has been running for a few years and is well-established in our industry. After covering an event which we have covered many times previously, we had this message exchange.

Client: Hello, we didn't know [photographer] was going to publish the photos in your magazine. Please show us what he sent you, at the time we didn't fully understand that it would be published.

Me: What is the problem here? If you have a press photographer attending an event, then if course the photos will be submitted for publication. You can see the finished issue on our site.

Client: No, that's not how it works, it doesn't give him the right. We didn't want to be featured in any magazines this year.

Me: Then please take it up with [photographer] as we cannot control what is submitted to us if we're told it has been cleared for use.

Client: But having a press photographer at your event doesn't give them the right to send pictures to a magazine!

Er, yes, yes it does. That's exactly what it does. A much longer conversation ensued in which we had to remind them again and again that our policy puts liability on the photographer, and they should talk directly to him; ask them if they had a contract asking for non release of the images or giving them copyright over them, which they did not; explain copyright law and laws of consent; and finally ended with us politely letting them know we would be happy to add a note in customer files that their events were never to be published again. And now that's one less nuisance for our team to deal with in the future!

I was designing packaging materials for a client who really, really should have shown more interest in the process.

Me: Here are three different treatments. Which do you prefer?

Client: I don't know, you're the expert. I trust you.

I went ahead with the one that I thought best fit the client's needs. Two months later all the designs were finalized and about to go to print.

Client: You know - I think I preferred that blue one. It's probably too late to change it now, huh?

Yes. Yes it is. 

I once had a client who didn't like that the Google map plugin on their site showed some of their nearby competitors.

Me: I can't just alter Google Maps.

Client: Find a way.

I wound up up having to just take screenshot, crop it, upload it to their website and link it to Google Maps. Unreal.

Client: I'm looking at this on different screens and it's a different size. It should be 6 cm no matter where I see it.

I'm still haunted by the image of her taking out her ruler to check.

Client: The site looks good, but what's with this writing on the photos?

Me: Those are watermarks. I'm using stock photos, and before I commit to buying them for you I wanted to make sure you liked the design - so I'm using the free version with the stock branding.

Client: So what's wrong with the design?

Me: What? Nothing, they're stock photos.

Client: But something's holding you back. If you're not sure about this photo, why should I be?

Me: ...