I am a personal assistant for several people in NYC. My main client cut back the hours she needs me. This led to a frank discussion about money and why I was looking for new clients.

Client: Why are you looking for more work? I cut back your hours because you were going on so many trips. You seemed financially fine.

Me I’m sorry, but you don’t get to choose how well off I am or not and then cut my hours based on that.

Client: I don’t know why you’re upset with me about that.

Me: Because what you did was incredibly presumptuous and has hurt me monetarily.

Client Well, let me think about this and maybe I’ll schedule you for more hours.

At which point she cut my hours even more.

I recently started a new job. One of our clients was up for renewal for our service and I was stressed they were not going to renew their contract because they had been exceedingly difficult to get feedback from or get a hold of. I'm talking 6 different follow-up emails before finally hearing back.

Thankfully, the client agreed to renew. Turns out they actually loved the service but were so busy they didn't have time to give feedback. This was before COVID started forcing business closures.

Yesterday I got a frantic call from my boss asking if the client had signed their renewal contract. I was confused, I wear a lot of hats, but the billing, sales, and contracts for the service fall under my boss, not me. I said I wasn't sure and asked if it was something I was supposed to do. He started ranting about how the world "had now changed" and who knows if the client would be able to sign now since all of their stores were now closed.

After we hung up I checked my email and found an email from him, which was a forward of what he had sent to the client with the contract attached, asking them to sign last month. He copied my manager as well, and asked if we had heard back. I skimmed it and then realized he hadn't even copied either of us on the original email! Neither of us knew he had sent it and weren't even involved in the conversation...

The client ended up signing and everything was fine but I think my boss still thinks this is somehow my fault.

I brought up a marketing idea in a meeting, and it was shot down condescendingly.

Client: We don't really do things that way. 

He gave a reason, but it didn't really make sense.

I was invited to a lunch and learn that afternoon where they brought in another consultant they'd worked with before to give a talk. He recommended doing exactly what I'd said. This time the client nodded his head approvingly. 

What the hell. 

Verbatim conversation I just had with a small business client that might as well be every client I've ever had. 

Me: What's your budget for this campaign?

Client: Budget? Campaign? Why are you asking me all these questions?

I produced a video for a client with lower thirds, captions and other design elements.

Client: What’s that font? It’s not in our branding.

Me: It’s Droid serif. It’s in your guidelines. 

Client: No. It isn’t. 

Me: I just double checked. Right there, under “video.” Droid Serif.

Client: Oh. Well. And what’s that color? It’s not in the guidelines. 

You can guess where the next couple of minutes go. Eventually I’m directed to a video on YouTube, commissioned by same client.

Client: We’d like you to make a video like this. These colors and this font. 

The colour is green. The font is Garamond. Neither of which are in the guidelines. Which, incidentally, the client wrote.

I highlight this inconsistency. 

Client: Well…those guidelines are really just experimental.

My first client as a freelance designer was the owner of a fitness/massage place. She wanted me to redesign a leaflet for her business. She sent me her draft but wanted me to touch it up. Every change I made was suggested by her and looked great, but she hated each one. After sending it back and forth for about the 8th/10th time I receive an email from her:

Client: I don’t believe how long it has taken you redesign the leaflet. I will pay you but I will be using someone else in future. I just wanted something that looked like the original design but refined slightly.

I look at all the redesigns and see that they’re all refined versions of her leaflet.

Me: I’m sorry for the delay. Enclosed is my latest version – hopefully you like this one..

I just attached her original draft.

Client: This is perfect, thank you.

I was hired as a temp-to-hire Admin Assistant. I drove an hour to the low paying job. I have a college degree, and the role was painfully dull with ridiculous office politics. 

These people are so off-putting I don't know where to begin.

I worked directly with the office manager, who showed me various processes that didn't make much sense. The whole time she was "showing me around" she worked on her own projects and complained about how stressful her life was. 

Client: Did you drive? 

Me: Yes.

Client: Oh, can you show me your car?

Me: ...

Client: (standing at the door) Where's your car? I didn't see it in the parking lot.

Me: It's over there, at the end. .

Client: Oh OK, that's the kind of car you have.

...Yeah? 

The owner of the Business came over to the front desk and asked me to scan piles of vintage golf photos for his private memorabilia collection. 

As I did that with a smile on my face but a scowl in my heart, I also answered some phone calls and asked the Office Manager some questions about my role. 

A second manager came over to talk to the office manager to check in on my progress.

Manager: So, is she getting her new role? I mean, does she understand this? She seems kind of confused. Is she a good fit for this?

They were steps away. I heard every word. They kept looking at me while I scanned vintage golf photos. 

I was tasked with updating a website for a business in town. I went through some painful discussions with the team about options for a site that was not well-made by the previous agency.

The team was sarcastic and rude about the whole process. I managed to update portions of the website, and sales went up significantly, but there was still room for improvement. 

I offered plenty of suggestions for long-term plans for the site but left soon after because the experience was so unpleasant.

Two years have passed, and the website hasn't been updated in any significant ways since I left. The business sells products in a competitive industry, where online presence is crucial. 

I've heard they've tried to hire other developers, but had no success. I guess it's that dysfunctional to work on the site for all involved.

I used to work for an accelerator in California.  I moved on to other things months ago because leadership was a garbage fire, but I've made myself available on an hourly basis to help with IT projects and other quick items that take no more than a few hours a week.  This morning the VP of Operations texted me:

Client: The executive staff will be working from home due to COVID19, we would like to install some web cameras in the prototyping warehouse, and workspaces so we can connect from home to monitor"

They are still requiring everyone else to continue working from the office. Even worse, they're installing surveillance to make sure everyone else is still coming to work. 

I met with a local church leader who was interested in my skills as a freelance designer and admin assistant.

We knew each other from when I attended church on Sundays, so the conversation was partly a friendly meeting, partly an interview.

Client: How did you get started? 

Me: I started freelancing years ago and slowly built my skills and my client base. 

Client: Wow, that sounds hard.

Me: There were some tough times, but luckily my husband is very supportive.

Client: Well, I'm surprised your husband decided to stay with you.

What? Who says that? Who leads a church and says that?