Many years ago, I and a buddy were hired to develop our very first website while still students. We had it done in two days or so because it was a simple site and we were excited to do the work.

We called the client on speakerphone so we could both hear what he said. 

Me: The website is done, we can bring the CD tomorrow. We only accept payment in cash as per the contract, please have the money on hand. In the mean time we are setting up the hosting for you.

Client: That's great, deliver the file and I'll pay you in a couple weeks. I'm a bit short on cash right now. 

My friend was shaking his head vigorously. 

Me: No. We can wait for when you have the money and finalize it then. We're still setting up the hosting anyway, so if it will take you a week or two to arrange payment that's fine. 

Client: *click*

He hung up, and we never heard back. 

Years ago when I was just starting in my field I worked for a small start-up company, designing their first product.  The work went well, but as always in R&D there were a few dead ends which we got pushed to "try anyway" because of some mysterious reasons known only to the manager.

The conversation below happened a few weeks AFTER we (3 engineers) finished the contract and were supposed to get paid.

Me: There's been quite a delay in payment. I know the company is well funded - why the wait? 

Client: Well, it's just that we`re reconsidering your payment based on your hours.

Me: What do you mean? the rate is in the contract... and frankly its quite low for the work we did!

Client:  No, it's not the rate, that's fine, it's the hours. A lot of the work didn't you did didn't wind up in the final product.  

Me: So you're saying that even though we agreed on this low-low rate, and did the work, and the project is done correctly and will enter production soon, and we are happy with all that, you want to ignore half our hours because the avenues you pushed us on didn't work out?

We got our payment the next day, but to this day this is the craziest thing I`ve ever been told by a client/boss/manager.

I started working with this creative agency that had this new high profile client. The client was a big pharmaceutical company, and most of my design work wound up being for them. They didn't give enough time for anything; basically every day I was working on several big campaigns that had to be turned around in two weeks. 

Even though it was stressful, I ended up adapting to their way of work. I stayed late on most days. 

The thing is that the pay was very-very low and I started to realize how important was my job for them. This pharma client was the biggest we had and was very demanding.

I asked for a raise. They downplayed every reason I gave them to demonstrate I deserved more.

Me: I'm working a ton of extra hours for this client. 

Client: We don't pay extra time. This is just normal for agency life. 

They looked me with a straight face while saying this.

I stayed for almost a year more after I asked for a raise (I still don't know why). I received a pitiful "yearly raise" and realized that it made me more angry than anything. I started looking for work that paid better, found it, and quit.  

Two months later, I talked to an old friend who was still at that agency. Apparently when I quit nobody could keep up with the workload for this client. They had to hire two extra designers to keep on top of it. 

Me: (replying to a public inquiry that included a budget) Hi. I'm able develop the site for you. Here are my references... However, it would require a bigger budget. Can you do XXX?

Client: Thank you for your quote. However, this is my 4th time inquiring for the site and I've gotten a lot of different quotes. I know it's possible to develop it in the stated budget.

Me: But you haven't hired anyone in that time?

Client: It can be done. Goodbye. 

I met with hiring managers to discuss a contract full-time sales/outreach job with a team in a large city.

Client: We can only pay you a low hourly wage.

The position would be supporting the entire local group, and they have nice offices with lots of well-paid admin staff. 

Client: A big part of the day-to-day involves driving around the city to meet with businesses and other organizations. You'll make speeches, establish partnerships, and help raise funds.

Me: Are the mileage and gas covered by the group?

Client: No.

So they want someone to be the public face fo their organization but let that person fall into debt over time. Not feeling good about the longevity of this position, or of this group. 

I have a client who in the past paid his invoice either on the due date or a few days late. They have also told me they have cashflow problems (big red flag right there).

Client: For the next project, we would like to have longer payment terms. We don't understand the problem. We have clients of our own that pay only after 3 months.

Me: My company is just me and I need to be able to pay my bills, too. I expect clients to pay their invoices on time.

Client: If I knew you were living on bread and water, I would consider paying you earlier.

Wow, that went non-professional real fast! "Why should I pay you if you aren't starving?"

I do translations, editing, and proofreading for academic researchers.

A client approached me asking for a translation and editing job for a friend of hers. Turns out the "editing" referred to taking a full 300+ pages research report and producing a 25-page paper out of it.

Me: No.

Client: Okay, that's fine. But we still need the final paper translated and edited. Can you do that?

I said yes, and sent a quotation and a timeline. They approved. 

It took three months before they sent me the documents. 

Client: Can you speed things up and lower the price?

Me: I can hurry things along, but I'm not changing the price.  

I delivered every stage a few days ahead of schedule, and yet she kept asking to speed up the job. When I finally delivered the final product:

Client: This was overpriced. I'm going to pay what I think is fair. 

A "Pay What You Want" client from hell.

After stumbling across my pet-portrait commission work through social media shares, the "client" private messages me and sends me a (low quality, face barely visible) photo of their pet.

Client: Can you draw from this photo? If you did this and shared it to my social media feed your following will definitely double! 

Me: I'm currently taking commission bookings if that's something you're interested in?

Client: I was thinking that it would be a charitable donation. It would be really popular with my audience and I'm absolutely certain it would get you lots of sales!

At this point I was stalling for time as I racked my brain for a client-friendly response. From previous experiences where (paying!) customers have shared my work, sharing to this size of audience definitely doesn't guarantee more sales.

Client: We could even get my audience to make decisions about the creative direction of the piece! There could even be a promotional campaign where a percentage of the profits from your future sales goes into my charity! 

Me: I can't work for free, I'm very sorry.

(I then provided information about my fees and explained that I'm fully booked for several months so would have to wait their turn if they were to book now)

Client: Oh. Okay. 

I felt a bit bad about knocking the wind out of their sails, but I think I dodged a bullet. 

I worked with a client for longer than I should have. These are every I Should Bail!" moment from every step that I stupidly ignored because I was trying to help a friend. It was cathartic to document the torture:

I received a freelance job through a friend for a logo design, brochure, and business card for a boutique wealth management startup company targeting only high-income clients.  On the first meeting, the owner said everyone in his business uses images like luxury yachts. and he wanted something different that stood out and was simple and sophisticated. 

I submitted some logo designs. They didn't even respond to the design and just sent me a logo they hacked together form Google Image Search results. Of course, the images were of luxury yachts.

I Should Bail! Moment #1

Me: Where did the image come from? Make sure it isn’t copyrighted.

Client: It isn't copyrighted. They came from the internet. 

Me: Honestly an original design is always safer. I will be working on the brochure next. The design process takes time so if he could give me until next week I would appreciate it. The result will be better in the long run.

Client: Well we made it from things we found on the internet, so we should be fine. 

I Should Bail! Moment #2

Me: Do you want me to work on the business card design next?

Client: No, he wants to play with the design himself...

I Should Bail! Moment #3