I discussed potential digital marketing opportunities with the manager of a big business in town. I saw a path to a significant ROI, but the client didn’t understand the value of what I was presenting.

Client: We’ve already done a lot of marketing ourselves.

Me: I see that, but a lot of it is very outdated. Effective marketing changes over time. Your primary strategy is outdoor billboards, and I think you need to turn your attention to online spaces.  People are very influenced by what they see online, via e-mail campaigns, blogs, events, and more. Traditional marketing techniques still have value, but if you aren't exploring these other avenues you're doing yourself a disservice. 

Client: We’ll think about it.

Months later, I found that they posted a job listing for a “Secretary” with "social media skills."

To this day, I drive by the same cheesy billboard. It has garish colors straight out of the 80s and hasn't changed in three years. 

I'm a web designer. I met a new client in a meeting for a completely different business and ended up chatting about his web development needs. Long story short he asked for a quote on an e-commerce store that I sent right away.  The client took a week or so to consider then signs the agreement and paid a 70% deposit per my terms.

However, he refused to give me ANY details on how to access his Cpanel or anything to do with his site - probably because he didn't know how. Frustrated, I tried sidestepping him to get the job done. 

Me: I have spoken to your host and they agreed to install WordPress on your domain and provide me with the login details, but they need you to phone and authorize this. I see no other way to help you without access to your Cpanel. Please note this means you are NOT hosting with me and will not have to pay my hosting and maintenance fees, however, this also means you will NOT qualify for the perks listed in my contracts under my hosting. No hard feelings, just making sure you are clear on this point.

Client: This is ridiculous, why do I have to make a call this is part of what YOU are supposed to be doing!

Me: Picture this, if you ask your mechanic to fix your car and you agree on a price but you refuse to allow him to access your vehicle, do you still expect him to magically be able to fix it for you? 

*Silence 

Client: Ok fine I'll call them. 

Client: What is this PDF? We need to send a vector file to the printer! Give me a vector file! 

Client: I would like a website to promote a book that I've written, so people can buy it.

Me: Okay, so you need an eCommerce platform so people can buy it from the site?

Client: No. They can fill in a form and then I can invoice them, and they can pay by cheque. No one buys things online, it's not secure.

Me: I assure you, people do, and we could set it up with a very secure payment processor.

Client: No one who wants to buy MY book would be stupid enough to enter their card details online.

A few years ago, part of my job involved keeping a commonly-shared Excel spreadsheet updated with test cases and test outcomes.   

One day I decided to hide some of the columns temporarily.  I forgot to "unhide" them, then I saved the spreadsheet.  Dumb mistake, but no big deal, right?  

Client: DID YOU DELETE THOSE COLUMNS FROM THE SPREADSHEET?

Me: Oh!  No, but I DID hide them and accidentally saved the spreadsheet that way.  Sorry about that.

Client: Sorry?  SORRY? Have you any idea what you've done?

Me:  ...but ...it's not that big a deal, is it?

Client: (looking like he wants to hit me)  Are you joking?  We've lost all that work!

Me:  The data isn't lost - it's just hidden.   

Boss:  What are you talking about?

Me: See?

I un-hid the columns. The client stomped away without another word.

Client: Can you get rid of the triangle at the start of every video?

Me: There isn't one. You don't mean the play button, do you?

Client: Oh....

Three minutes later, after they'd checked:

Client: Yes it was the play button. I just prefer it at the bottom of the screen. Can you move it?

Me: (after laughing uncontrollaby for five minutes) Yeah I don't have control over that. Maybe check your preferences.

Client: Is 128 gsm art card thicker/firmer than 128 gsm paper?

Me: It is the same weight so will not be any different.

Client: BUT one is paper and the other is card. 

Me: ...Card is paper.

Client: What? No, it's not. 

Many years ago, i worked at a Kinko's (I know, all you designers are grinding your teeth just hearing the name), and one day, a customer brought in a "PowerPoint presentation" they wanted to be printed out.  The entire thing, all 50+ pages of it...was done in Excel.   With no print areas set, and no formatting.   If I had attempted to print it out, as is, none of it would have printed properly and would be mostly cut off the page.  

Client:  You can fix this up and have it ready for my presentation tomorrow, right?

Me: If I stayed here all night, and worked unpaid overtime?  Probably.  It'll cost you about nearly $1000 for the time and effort required to fix it.  

Client: Nevermind!  I'll just do it myself.

Never saw him again after that.  Sometimes you've gotta pick your battles, and quote a price that seems...believable, but is still more than they will pay.  

Client: I can't pay that much for this project.

Me: Okay, how about this- I give you a 40% discount and in return I get 10% royalties from any sales of the game, gross, in perpetuity.

Client: Make it a 50% discount and we're good!

Client: My internet isn't working!

Me: What have you tried already?

Client: Everything!

Me: Have you turned the modem off and on?

Client: Yes! I’ve tried everything!

I pulled out my handy list of troubleshooting steps and started going through it, performing increasingly drastic fixes. None of them worked.

I didn't bother rebooting the modem, because they told me they'd already done it.

Later, the client was looking at my troubleshooting checklist over my shoulder:

Client: Turning the modem off and on? I haven’t tried that yet!