“The wedding was held by Baby Hope Diamond’s owner Wendy Diamond, an animal welfare activist, to benefit the Humane Society of New York with all of the ceremony’s goods and services, which included a celebrity wedding planner, a pet buffet and an officiation by Triumph the Insult Comic Dog, having been donated and guests purchasing tickets to attend.”
On possibly the worst day of my life, I got a job off craigslist designing wedding/bridal shower invites for this stupid fucking event. Then the original dog, Lucky Diamond (famous for being the dog most photographed with celebrities), died (she had cancer; yes, her owner was throwing a wedding for her dog who was dying of cancer) so the crazy dog lady adopted a new one, gave it the same name but put “Baby” in front of it, and had the wedding anyway. She’s an animal welfare activist and is donating the money to the Humane Society, so that’s good, but I have never been more condescended to and personally insulted by an employer than on the day I worked for her.
The craigslist ad said that she needed someone who knew Photoshop and InDesign. And when I talked to her on the phone before she hired me, I confirmed that she needed just Photoshop and InDesign because pretty much every “Graphic Designer Wanted” ad wants someone who knows Illustrator and I don’t know Illustrator. She confirmed, yes, just Photoshop and InDesign. Awesome, I accepted the job and she asked me to be at her apartment at 9 a.m. Then I got an e-mail two hours later asking me to be there at 8 a.m instead. Awesome, fine, whatever. It meant I had to get up at 6 a.m. but I was gung-ho, I was full-time unemployed and I had finally managed to find a small freelance gig. Everything was going to be great.
I got there right on time, I made sure to be friendly and smiling because I could tell she she was in a complete panic because her full-time designer had gone on a last minute vacation and she was desperate for these invitations because the bridal shower was scheduled for the following week. I did my best to be reassuring and positive and I got to work right away. I thought it was hilarious. I’m designing dog invitations! I tweeted something about having the most ridiculous job that day and being thrilled about it because…DOG WEDDING INVITATIONS. Such fun!
I could not have been more wrong. I started designing the invitations, which immediately became an ordeal because she didn’t understand how .pdfs worked so every time I adjusted the font slightly in InDesign I had to reexport it as a .pdf and then from the .pdf as a .jpg. Even though she was sitting 10 ft behind me, she refused to look at anything unless it was e-mailed to her…and this happened like 20+ times which means I had 40+ different variations of the dog wedding invitation on my computer. Also there was no dog groom at the time that the invitations were being designed and she kept complaining about the big blank space aka where the groom’s name was supposed to go.
But that was just the tip of the crazypants iceberg. I can handle nitpicky clients. I kept thinking of Clients From Hell and telling myself, “Okay, this is the real deal. Clients are stupid and ask for ridiculous demands but it’s my job to make what they want happen, that’s how this works. Just buckle down and do it. You can do it.”
Rough layouts for the invitations complete, she then sent me some caricature/logo drawings the vacationing designer had drawn of herself and the dog to put on them.
And of course…
they were
all
in
Illustrator.
Luckily, by chance, earlier that week I had sat myself down and done some basic Illustrator tutorials (in what turned into an incredibly frustrating 6 hours) so I had a basic understanding of the program but these were professional, stylized caricatures and she wanted me to change the clothes and put hats on them and take the dog out of the basket it was sitting in and put it in a wedding dress and then have her caricature holding the dog caricature instead of a teacup, etc, etc. So I had to explain to her that I didn’t know how the program worked and even if I did, I’d be working with someone else’s art style and that you can’t just take an illustrated dog out of a basket and put it in a wedding dress easy-peasy because it’s not like the illustrated dog’s body exists behind the basket…I’d have to hand draw the dog’s body to match the drawing style and that’s just not a task for a beginner. She didn’t understand at all.
In fact, she looked me directly in the eye and said, “You just have a bad attitude, that’s what this is. If you think positively, I know you can do this.”
…
As though if I just smiled, I’d be magically endowed with mad Illustrator skills.
“It’s not an attitude problem, it’s a skill set problem,” I muttered under my breath. She may have heard me, I don’t know. Probably.
“Photoshop, InDesign, Illustrator…they’re all the same, right? They’re all in competition or something. How hard can it be, really? Just stop complaining and think positively. You’ll never get anywhere in life if you can’t think positively.”


I can’t even go into more of how horrible that day was. I haven’t even touched on her personal assistant who really was incompetent and her “yes-woman” who looked sort of like Barbara Streisand and would hover over my shoulder occasionally saying things like, “Tsk-tsk…the clutter in this office, how do you deal with that? You need to clean it up, clear a pathway in here. It’s a metaphor for life. If your office is a clutter, how will you ever make it through?” (even though all I had brought with me was my backpack and the clutter was all there when I arrived) and “What do you mean you aren’t supposed to use more than three font sizes? I know what I’m talking about. I used to be the lead designer for Animal Fair magazine!”
Look, guys, I want you to understand that I really, truly tried my best to make everything work. This was my first professional freelance graphic design gig. I wanted so badly for it to go well. I looked up tutorials for hand-drawing in Illustrator and reminded myself over and over and that I had been meaning to learn Illustrator anyway so I shouldn’t look at this as a problem as much as a high-pressure opportunity to do so.
I ended up sort of getting the dog caricature into a wedding dress, but honestly it looked more like it was wearing a ghost costume with flowers on it.

She only paid me $100 (which is fine, that’s what we agreed on in advance), even though she also had me do some stuff that I have a regular freelance rate for which is considerably higher than $100/day…like setting up her PayPal account (I spent a good 45 minutes on the phone with them on her behalf), explaining to her how Facebook and Twitter work, fixing some of her WordPress layout and oh, did I mention she didn’t let me get lunch or offer me water or anything to eat? She offered me a slice of her lean cuisine microwavable wheat pizza around noon, but that was it and I said no because yuck.
I’ve been debating whether or not to write about this ever since it happened in May — she meant to have me sign an NDA but never actually did…and since that was mostly to prevent me from leaking top secret details about the location/guests at the wedding and the wedding is now over…I hope you enjoyed the story of one of the worst work days of my life. Please don’t send this to her.
tl;dr crazy dog lady is crazy.
Pictures: “A Look At The World’s Most Expensive Pet Wedding” | BuzzFeed