Client Madness: 5 Freelance Horror Stories

Joshua Kraus
Joshua Kraus

Are you checking your calendar in confusion? Turning on the radio to see if they’re playing Monster Mash? Don’t worry, you’re not crazy, and Halloween hasn’t come early. Nevertheless, we’re running a bone-chilling, goose-bump inducing article in the merry month of March.

Why the anachronism?

Simple: Freelancers deal with horrific clients and wacky assignments year-round. It doesn’t matter if it’s the end of October or the middle of May, a normal day at the office (aka, the kitchen table) can take a turn for the terrible in the blink of an eye. The least we can do, then, is share these fearsome exploits with the world. In them you may find a less worth learning, a surprising nugget of wisdom, or, at the very least, some needed entertainment.

So turn out the lights and curl up in your favorite blanket. Here are a few freelance horror stories to scare you straight.

Joel Klettke

Joel Klettke
Trade: Freelance conversion copywriter and content marketer

One of my first copy projects ever came in through LinkedIn – complete with a smiley-face in the subject line. The message itself should’ve struck me as odd – asking “How quickly can you get to my office?” and “I look forward to getting to know you.”

Regardless, I decided to follow up.

The guy more or less refused to chat on the phone or even review my portfolio – I sent resources, but he didn’t bother to look. He just insisted I come down to his office – on the opposite side of the city – and meet with him. No details on the project – nothing.

These days, I never would’ve gone – but back then, I was green and eager to make new connections, so off I went. I sat in his office as he rattled on – and then SAT at his computer reading stuff I’d written in the past, giving it a quick once-over. We accomplished nothing in that meeting other than shaking hands – he gave me a sharpie pen. Then it was back home.

Later, he decided he had a project for me, so he wanted to meet – AGAIN – to talk about project specs. So I drove clear across the city – AGAIN – to hear what he wanted. It was a project all about 3D mail – he wanted me to do spec work to prove I knew what I was talking about. I told him I didn’t do spec work and gave him my rate. He hummed and hawed, but agreed to it, sending me on my way again. 45 minute drive ONE WAY, 15 minute meeting.

Then, I did the project, sent it off and … didn’t hear from him.

So I emailed. And then I emailed again. I kept emailing and emailing, but I got nothing. I could see my invoice had been looked at, but not paid. I got more and more annoyed. Months went by. Six of them.

I began hearing horror stories of non-payment from other freelancers in my city, and decided enough was enough.

We were coming up on Christmas, so I decided to send him a little “3D mail” of my own. I sent a HUGE gift-wrapped package (we’re talking roughly 4 feet by 2 feet) filled with packing peanuts, an invoice, a letter and some condoms (in case he wanted to screw any other freelancers).

And I filmed it. You can watch/read here.

He promptly paid my invoice, and we never connected again.

Now, that’s a funny story – but I’m a little embarrassed by how I responded, and I’ll never, ever do that again, even if it worked.

I’ve grown up a lot since then. So … what did I learn?
To have a contract, get at least 50% payment upfront and always trust your gut. If someone feels sketchy from the beginning, THEY ARE. Don’t work with them. You don’t need the money.


Trade: Freelance copywriter

(Haley chose to remain anonymous, because if the wrong people read her story, it might be just too awkward to handle)

So I moved to a new city where a former student of mine (from one of the reputable ad schools) was working in the ad industry. I was called into his current agency for a freelance gig. I saw him in the hallway and we said our hellos and caught up with each other’s lives. The next day when I came in, I noticed he wasn’t around.

Then I found out he got laid off that morning, and I was actually brought in to cover for his clients while they replaced his role at the agency. AWKWARD.

Fast-forward to two years later and I get called into another big ad agency. Lo and behold, this is where my former student landed after losing the other gig. We said our hellos again and laughed about how I was his temporary replacement from his last job. Whew! No hard feelings and the air was cleared.

I came into the agency the next day and, once again, found out he had just gotten laid off. I have a feeling he probably refers to me as the Dark Angel of Job Death, or something like that.

Kendall Egan

Kendall Egan
Trade: Freelance marketing strategist

I worked for an idea incubator as a freelancer for 18 months. We worked remotely and chatted regularly on projects via Google Hangouts. There were four of us: three women and one man. The male managing partner was dating the other female partner, which was not a problem until they went through an explosive breakup.

The last two months were very awkward. For example he started crying in one meeting and abruptly canceled it. After about six weeks of he-said-she-said, the managing partner unceremoniously fired the other partner on all sorts of trumped up charges. He knew she wouldn’t pursue anything legally. Then, I decide to leave because I had worked more closely with the female partner, and even though he said he would pay me on our exit interview and in writing several times, he stiffed me.

Again, he knew I would not pursue anything legally because it just wasn’t worth it financially. We are both hoping karma takes care of this guy!

Hope Alcocer

Hope Alcocer
Trade: Independent contractor and communication lead

My client had a less-than-par product she wanted featured in Vogue and other top magazines. I knew it wasn’t possible, suggested as such, but she wanted me to try anyway. After months of unsuccessful attempts, she became very angry and demanded a summary of my work and time. When she saw how much time and effort I put into it, she decided to ask for a refund for that amount, because she had wasted her time on me.

I refused to do such a thing, offered a portion of what she was asking, and she took me to small claims court. The date was a date she knew I would be out of town, so the case was automatically awarded to her and that amount was owed.

I have been in touch with a couple freelancers nationally, and they all have had the same story. Her PR company in NYC even fired her!

I learned to always have things in writing, don’t take on a client JUST because they’re a new client, and analyze the situation. Is this a GOOD business move for me? Will it bring more stress than it’s worth?

You CAN fire your clients. I didn’t want to so I wouldn’t lose business, but we shouldn’t take on work we know is destined to be a failure.

April Jimenez

April Jimenez
Trade: Former freelance copywriter, current digital marketing manager

I am no longer a freelance copywriter, but a few years ago I took time off after having a baby and decided to supplement my income freelancing. Being a new mother, I took on very small jobs, and I never took on anything that had a quick turnaround or tight deadline.

I had a client that I worked for pretty regularly in the executive recruiting space. True to form, the projects were small and long-term, so working at night after the baby was asleep was fine. One day the client approached me and asked me to take on a project with a tighter deadline than I was used to. I told her I wasn’t comfortable with it, and she assured me it was an easy task, and that even though the deadline was hard, I still had some leeway.

Lucky for me, I finished the project the three days before deadline, but I left it until the morning to look over with fresh eyes.

Then Superstorm Sandy hit (and while I completely understand that I should have sent the information over before the storm, with a four-month old and a house to worry about it, it wasn’t the first thing on my mind) I was without electricity for five days. The client refused to accept that I could not access my computer and was stuck in a house nearly underwater (she was in the midwest, Sandy only really hit the east coast), I ended up sitting in my car, with a crying four-month old, rewriting the entire project from scratch on my phone so that I could send it over by deadline.

To make matters worse, she refused to pay me for that project, or two others I had completed earlier that month, because of the anxiety it caused her.