40 Freelance Horror Stories That Will Make You Cringe
Freelancing has a lot of great benefits: flexibility, time freedom, and in many cases more money than you could earn in a job. With more people considering freelancing and big businesses jumping on the freelance revolution, there are a lot of opportunities coming. But for every success story, there is a horror story. We’ve rounded up some of the top stories from different freelance horror story Reddit threads. From the crazy to downright nasty, here are the worst freelancing horror stories on the web.
Some of the responses may have been edited for clarity and length.
1 – Don’t fight in front of the freelancer
I was hired by a company who was run/owned by 2 people, both equal partners. The catch was they were a former married couple who got divorced.
I show up 45 min before shoot is to begin. The ex-wife showed up with her own clothes and that started an hour-long fight that ended up with the ex-wife making the models take off the clothes the husband gave them and cutting them into pieces with scissors. The husband threw mud on top of the dresses the wife brought, with the models hiding in their cars.
Both tried to refuse to pay me and claimed it was my fault for not shooting their idea, but the threat of small claims court got my shooting fee.
2 – Derek sucks
About 10 years ago I used to do a lot of work for one newspaper. Another freelancer did a lot of work for them too, Derek.
One day I got a phone call from an event organiser, asking me to photograph their event. I told them that was Derek’s gig. The organiser said they still couldn’t get hold of Derek, had no idea if he was going to turn up or not. I reluctantly agreed.
The day before the Games I got a phone call from the newspaper. Derek had phoned the editor and told her that I’d stolen the job from him. That newspaper refused to work with me ever again. F**k you Derek.
3 – The wrong kind of grand finale
When I met up with a client he explained that he wanted to make a documentary about his dead son.
The day of the shoot we drove out to the desert. He began to empty the contents of his van to set up his scene including 2 Manikins (man and woman) sitting at table eating dinner and a shit load of ketchup.
He loads a few 22 caliper pistols and a shotgun and asks me if I am ready. I roll… he shouts into the camera for a bit and the unloads into our dinner guests.
4 – A regular stiff
Apparently, working with a bankrupt company is a bad idea. Unfortunately, freelance horror stories start, as too many do, with the freelancer not knowing about the bankruptcy:
I got hired through a production company, not an ad agency (as was usual). The agency had big overage charges from my work, though. But because the agency was responsible for overages, not the production company, the production company wouldn’t pay for the overages and I got stiffed for several thousand dollars.
5 – It’s called a “value exchange,” look it up
I had one client that took me out for coffee, complimented my work (I’m a freelance writer), and said he really wanted to help me out. Of course, when it came to scoping, he talked about how his company was young and new – so he didn’t have a huge budget. First red flag, but I was an idiot. Anyway.
Long story short, he hard-balled me on price so much that I ended up agreeing to a rate that was about half my full rates at the time. In exchange, he said he would provide mentorship and free consulting to help me build my business (ohhh the irony). At the end of the day, he not only didn’t deliver on his end of the bargain but also kept pestering me to do more for him – help him find other freelancers, help him get backlinks to his content (not the project we scoped) and more.
6 – From wedding to wake
I had posted an ad as a wedding photographer. Guy contacts me and asks if I’ll do a wake. I say sure but… Won’t it be a little dark of a situation for a photographer? He assures me not to worry, that it will be a happy event with lots of good memories.
So I show up with all my gear and start shooting like I would any other event. I got so many weird looks from people, even some scowls from some older folks.
Ended up with lots of pictures of people crying and hugging, pics turned out fine and the client thanked me, paid me, offered to write a review or recommendation, then I never heard from them again.
7 – Shady marketing department
I was asked to shoot a product/lifestyle video for a company that produces women’s fitness leggings (I.e. yoga pants with pockets, basically). They don’t have a marketing department or anything but they’re also wildly successful.
So I show up to the shoot, do my thing. I chop up two edits, one 30 seconds and one 60 seconds I send it over. They don’t like it. Ok, I’m fine with that. I politely declined the project and wished him luck.
A week later, a friend messaged me with a couple links to their social media channels that featured some of the work I made for them. Now I’m peeved. Emailed ‘ol buddy and told him that if he wished to use my work he could purchase the rights to them for $X and that if he declined then he needed to take down the content. He blamed his “marketing team” for using it…
8 – Gosh darn realtors get you every time
I was contacted by a real estate agent to do a video interview thing for this community series she wanted to start.
The Realtor grilled this poor teacher for almost an hour, asking where she was from, where she has taught before, what her perspective is on current events (cyber bullying, school shootings, kids sexting). I had to stop the interview after 19 minutes (max run time for my DSLR is 20) and said “We’re at 20 minutes, do you have a lot more questions?” She said, “Just a couple more.” A second time, “We’re at 40 minutes, I think this is plenty of content…?” She said, “Oh but I haven’t gotten to my most important questions yet!” Ugh. I was there for almost 3 hours. It was only supposed to take 30-45 minutes.
9 – Can’t you see how bad you are?
I once had a client that was super friendly to start. He even offered to pay me more than the rates I quoted – he said my rates were too low and he wanted to pay me fairly. I was over the moon as a new freelancer.
Then the client sent me about 100 pages of “brand decks” and told me to create brand relevant content. That was about it. No other guidance. When I asked for clarification, I got told I “had enough” to go off of.
I did my best and delivered an article. The client then invited me to coffee. At the meeting, he shoved a printed copy of my article back in my face and said “can’t you see how bad this is?” over and over. I politely told him we couldn’t work together anymore and promptly walked out the door. What a jerk.
10 – It’s from scratch, I swear
Our production company was getting off the ground and we decided to shoot a free commercial for a cupcake bakery. The owners said they give us two dozen cupcakes for payment. Sounded good to us. Well we show up to shoot and the owner tells us we are not allowed behind the counter or in the baking area because she didn’t want us stealing her secret recipe. The shots were utter crap cause all the display glass had fingerprints and it was impossible to get anything remotely appealing.
We edit the commercial and send the cut to the bakery for review. She sends back this livid response. She was super upset about us using a text reveal that said all the cupcakes are made from scratch. “From Scratch” was literally part of their company’s name. She said if we didn’t remove it she was going to leave us negative reviews all across social media. We ended up never posting it or responding to her.
11 – The nerve of some people
Unfortunately, some freelance horror stories start out with the best of friends:
My best friend is planning his wedding and he wants me to shoot his wedding. Usually I work in a team and we get between €1,000 and €2,000 for a half day shoot. I told him that he doesn’t have to pay me, only my partner.
He was like “wow that’s expensive”… I’m disappointed, he’s receiving a 750€ wedding gift but doesn’t realize it.
12 – “But you’re so muscly!”
Not my client, but I went to an event on behalf of a client and had to work with the onsite agency. I’d done this a bunch of times before, so it was no big deal.
The day was going fine, but the agency leader kept asking me how much I would be writing about the event, what kind of coverage I’d be doing (I’m a freelance journalist), and when I would be submitting my stories.
Then another person from the agency came up to me. Without prompting and before I’d even said hi to her, she grabs my arms and says “oh my god your biceps are so big!”. I didn’t even know how to react. But I told my client and I think she ended up getting taken off the project.
13 – Lowballing always costs you
Last spring, my barber’s boss asked me to take photos of his wedding. I just wasn’t aware of the work load. I’m used to doing 30 minute senior photo sessions and having a small work load.
We agreed on $300 which to me didn’t sound bad at all. I got a list of what they wanted and basically I would have to be there from 7 am ~ 5 pm which to me didn’t sound bad at all.
I didn’t even come close to leaving at 5. I was there until 11 pm because of the pacing of everything and I had to be there for all of it. So about 15 hours of work on top of the week it took me to go through and edit over 400 photos made me realize my worth.
14 – Couldn’t get less professional than this
A client said he was trying to start a live recording business and asked if I’d give him a hand recording a gig for a popular local band. He said there were 16 live tracks. I try the computer, and there are only two channels shown. Where are the other 14? I start poking around and voila! 16 channels to choose from.
At this point, my buddy comes back. He looks bad – he’s stumbling, and more confused than before. He then pushed ALL THE GEAR off the shelf it was on to the floor 3′ below. Turns out that my friend is a massive substance abuser, and he’d actually gone out to have a drink and chug about 1/2 a bottle of Robitussin cough syrup. I was beyond pissed.
15 – The shoe killed the cable!
I was doing a corporate live gig. ONE microphone for one person. I show up and the crew has set up everything and I just run through and double check that the one mic is working etc. The speaker shows up and we have her check the mic; I get my level sorted out, all is well and we are ready to make a few easy bucks for the day.
The event starts and as soon as she begins speaking, nothing but hum on that channel. So me and the guy I’m working with begin to track down the issue. Not the board, not the amps; well shit whoever set this up ran the signal line under tables and someone’s chair or shoe has killed the cable.
So here we are in a room full of people waiting as we run new cable. From heroes to zeroes!
16 – Freelance horror stories part 16: from 8 page feature to 2 page listicle
Not everything a freelance writer does is published. That’s ok, but then there are clients like these:
An editor-in-chief once added some “atmospheric” information in a longform feature of mine, which were total BS and never happened. That was a shock, but not horror.
Horror: the same editor asked me to write a longform 8-page feature. I complied. Weeks later the article is published and it’s like a top 10 list on 2 pages. No Sorrys, no anything. Also: got paid only for those 2 pages.
17 – It’s 2 acres, I swear!
Sometimes there are red flags that, when ignored, launch freelance horror stories like this one:
I had a guy argue with me that his property was two acres, when it was clearly one. I resorted to walking it with him and my 100 foot tape measure, and doing the math on the back of my sketch. Nope, I was wrong. He could not tell me where the other acre was.
He was a buyer, who had been renting the place for years. The seller was the wife of a former governor who did jail time for, um, real estate fraud. I wanted to ask who they thought they should trust here, but I just declined to finish the assignment. Not one of my regular lenders, everyone would be mad, no point.
18 – Maybe don’t sexually harass the home inspector
I had a client get under contract multiple times, always backing out on home inspection. She was generally a pain, I would have dumped her sooner, but she came from a former client referral and I absolutely adore that guy.
Turns out, her reason for going through the home buying process multiple times is because she had a crush on the home inspector. He finally called me and told me she was reaching out to him at night and crossed the line into ‘uncomfortable’ territory and that he wouldn’t be able to perform any more inspections for her.
Sexually harassing the inspector was on the mild side of her bizarre behavior. I did finally fire her.
19 – 2 week project to 4 month nightmare
It was a 2 week project for my first corporate client that turned into a 3-4 month nightmare.
They said only intended to pay me for the initial 2 week estimated timeline. When I confronted the lead about him not valuing my time, he tried to convince me it was part of the design culture and I had to take all of the shit because the client was important in our area and could give me design work in the future (sounds great but I can’t pay bills with possibilities).
The revisions process was terrible, the client praised all of my ideas but ultimately didn’t know what he wanted, and the design firm was disgustingly unprofessional. Crap from start to finish.
20 – They own everything, even your ideas
I worked for a local nonprofit for 2 years as part of a magazine project as a videographer / graphic designer / journalist.
After working there for two years my whole team was given contracts that labelled us as interns, said we can’t create anything (even personal projects) without his permission, and said that if we were to quit we wouldn’t be able to practice our trade anywhere in the province. When I asked to renegotiate he said that it was a take it or leave it kind of deal.
After the weekend I walked in and quit.
21 – Don’t ruin my whole business, please
I freelance on a freelancing website. I make 3D images, usually products or interiors. And it’s my main source of income.
The client had made several attempts to get my email which I declined because usually when clients ask for email they are trying to take payment out of the website that I use. Which is a big no no. I can lose my account and my business for taking payment off the platform.
Anyways we complete the project. A few months later he called back and had another project. Again asked for my email. Bingbangboom first thing I get is one of his employees asking me for my bank account information so that they can send me direct checks.
I very professionally told him to f-off and find another freelancer.
22 – Chaotic evil client
I’m a Freelance Makeup Artist. I haven’t been working for long (about 2.5 years) but at the same time, I know what a short film set or any set should be like.
On the end of the 3rd day, the director said that he’d send out a call sheet to everybody by midnight or something. Ok, whatever. I ended up waiting until 1am for the call sheet before I eventually fell asleep but of course assumed Call Time would be at 11am because it had been 11am all 3 days. So when I woke up at 7:30 with the notification that the call sheet had been sent at 3 am saying that call time was now 9am I was livid.
I’ve still to this day never had another experience on set like that and I hope to never have another one like it.
23 – You already approved it, sir
Sometimes, freelance horror stories are that special kind of story. That kind when the client actually agreed with what you proposed but then somehow got mad when you delivered… exactly what you told them you would deliver:
Client: why does it look like that?
Me: why do you think it would look different than the final proof that you approved?
This happens way too often.
24 – You know that’s a lot of money, right?
For most freelancers, a bit of client tinkering is fine, if annoying. But then you get clients like these ones and you remember how awful it is when someone won’t let you do your job. It’s not even about the money at that point – there’s a certain pride that you simply have to fight for:
I had a client who would regularly google his brand name, and if our ad wasn’t at the top of the SERP, he’d go into the campaigns and boost every keyword’s bid by 10%. This happened at least every week, sometimes more often, and he would never mention it unless we called him out.
25 – A 1970s rocker in the 21st century. What could go wrong?
I worked with this eccentric rockstar who peaked in the 70s. He actually had a couple of hits, so it was interesting to get to work with him.
His website was just a standard showcase of his discography, his latest projects, news, merchandise, etc. No big deal. But it turns out this guy was insane. By the time we got done with the project (that went 8 months over budget), we had created the most bizarre website I have ever seen. It was almost something to be marveled at.
And after all of this…he says he loves it and pays us, then we spend 3 months trying to coordinate to get his domain pointed at our server so it could be “live”. We eventually gave up because he wasn’t taking any action and we had already been paid. To this day (about 4 years later) his website still has a coming soon page up.
26 – Cute and playful, or something
Artist here. I was at my first ever furry convention doing commissions at my booth. A guy commissioned a painting of his character – a blue dragon. No problem. When he picked it up he loved it. Brought three friends to my booth who all wanted to commission me… Awesome!
They all had blue dragon characters. Practically identical.
All four said they wanted something “cute and playful.”
I was so stressed trying to make the four paintings unique enough that they wouldn’t feel like they got the same thing as each other. SO stressful. On the plus side, all four were lovely clients and two ended up being repeat customers.
27 – “If you love children, you shouldn’t ask to be paid for your work”
It’s hard to pick the worst one but I would say it’s the one where I was illustrating a children’s book. My illustrations get approved and a month later a higher up would out of nowhere demand it to be changed completely. And they paid me late.
The pay was also low. Of course they wanted a lot of work done in a very short period of time so I was spending everyday drawing my butt off for them so I had no other income. There was a month I was running out of money and had to work at a shady restaurant for 8 hours and get paid next to nothing. At some point my client refused to pay and they asked me “Don’t you love children?”. Luckily I was paid in full and it was finished 🙂
28 – Real tears, guaranteed
Not a horror story in the traditional sense, but definitely an emotional roller coaster. It’s one thing to deal with loss. It’s an entirely different thing to have to live with the pain that this freelancer went through:
After a long year of fighting cancer and pneumonia and other health issues with our dog, we had put her down.
It broke my heart.
The next three commissions? “Can you paint my dog, we just put her down?” Nothing like doing watercolors with real tears.
29 – Just one thing, and another, and another
Worst was definitely when a guy wanted a picture of himself to be drawn. He provided me with his profile picture and stated the colors and details he wanted. All good. I finish the drawing and show him a preview of it, he loves it but decides, hey, edit my smile into a frown. I reluctantly redo like half of it, because you can’t just “edit” an expression, you literally have to redraw it all, because the eyes, nose, jaw, everything is affected by your expression. I show him a preview and he loves it again, but asks for the colors to be swapped around, and for his shirt, which in the profile picture he sent me had stripes on it, to be plain.
Mind you, back then I used to take a small deposit before I began, and the remaining amount after the drawing is done and the client is shown a preview of it. That was the tipping point for me and the reason I started taking the full amount as a deposit before I drew anything.
30 – Someone else can “fix” it, right?
Worst was when I was doing commission about 15 years ago I turned in a really rough sketch (my sketches are ugly).
The commissioner decided to give my artwork to another artist to “fix my mistakes” without asking me first if it was ok.
Didn’t even bother to ask me to fix it first, just straight up gave my work to their artist friend to fix.
It upset me a lot so I refunded the client, chewed them out, and told them to never do that to an artist.
31 – Pumping out words at the speed of light
I used to do jobs for an umbrella that encompassed 6 separate translation agencies, of which one or two were regular customers. I think they just tried to dump the shitty jobs no one else wanted on me.
One day, they called me while I was waiting to board a flight, to ask if I could do a translation due the same day (while I’d indicated I was on holiday in their online portal). I don’t remember the word count, but estimated the job would take longer than my wait time, so I refused. When they kept prodding, I explained I’d be on a plane in max. 1h and would be in the air for the rest of the day. After a short pause, they went “So… can’t you do it before you board?”
I couldn’t officially drop them because I didn’t want to lose the other agencies in that umbrella, but I refused everything they sent since then.
32 – Talk about demanding…
I do subtitles for students who major in film. I secretly do it dirt cheap, because I love short films and the effort gone into making them. It’s almost like a charity.
However, one client in particular felt the need to be a hotshot. They would say “Have this done by tomorrow, I’m busy” “What’s wrong with this translation” (nothing was wrong).
Yesterday, they contacted me Saturday at 7am asking if I was available. I answered at about 9, and the response was “Oh I asked somebody else because you didn’t answer”.
I won’t be working with said client any further.
33 – Two stories for the price of one
I had one client who would ask for my availability and then finish negotiating with the end-client for something completely different, but expect me to stick to the first deadline, no matter how unrealistic. Then if I said no, I couldn’t agree to the new conditions, they would get all bent out of shape.
I had a client that asked for a volume discount on large jobs, and told me that it was standard practice. I agreed because I really wanted the job and because I was new and just took their word for it that it was standard. Then after a few small jobs at the beginning, they started making sure that every file they sent was far over the discount threshold, so I would end up doing lots of free work for them. When I finally wised up and said I couldn’t continue the volume discount, they just stopped sending me any work at all. Good riddance.
34 – Translator client from hell
Last weekend an agency asked me if I can standby on Monday for a job that’s due the same day. They promised the file would come before noon, and they want it before 5pm.
Normally the answer would be no, but I’ve been getting less jobs from them lately, so I thought maybe I should make a good gesture.
Came noon today, no word from the agency. I waited until 2pm before I asked and they just said the client wasn’t ready.
Finally, at 5pm, the agency notified me that the client made a mistake. The job was for another language pair. Just like that, I wasted a day for them. Didn’t even offer an apology.
35 – The real freelance horror stories of Canada
I did work for a Canadian crown corporation. There was so much back and forth and revising it was ridiculous, but I charged them for my time (as well as the word count).
They said the last review was fine. I submitted the final document, and didn’t hear back for a bit. They finally contacted me trying to nickel and dime me, and claimed that everything was “wrong” and that the manager working on this project had to spend hours making corrections etc. None of it made sense. At the time, I had been working as a freelancer for 10 years and never had any such complaints!
They wanted to pay me a ridiculously low percentage of the original fee. I negotiated and didn’t get as much as I wanted to but I just wanted to be done with them. I tried getting some legal advice but it was hard to get anywhere, and I wasn’t in Canada.
36 – Oh I was off by an order of magnitude, sorry
When clients change their mind, that’s one thing. But withholding payment is truly the worst of the freelance horror stories:
My horror stories generally revolve around clients changing their minds on what exactly/how much they wanted. The worst part is then they start withholding pay until I’ve provided way more work than we initially agreed.
Most irritating early one was a client saying they’d mistyped and could I please do 10,000 words, not 1,000.
I now ask clients to agree on a very precise work outline first.
37 – Good golly your grammar is godawful
Of all the freelance horror stories out there, this one hits different:
I had a client demand revisions when they have worse grammar than me.
What’s the point of getting a writer if you’re just gonna insist you know better than the writer when it comes to grammar? The worst is when they change it after you write it so now it’s wrong, your name is on it publicly, and you had no say in it.
If my name will be in the byline, I make sure it’s in the contract that they print exactly what I send.
38 – When they steal your work and ghost
I had been freelancing for around two months. Really quick, one-off type jobs.
Then, I scored a big client who promised as much work as I could handle per day. He sent the article topics, keywords, formatting requirements, etc. All via Skype. Back then, I had no idea about contracts or the like. So, I wrote daily. About 4-5 hours per day. In total, according to his pay rates, I earned about $1,400 for two weeks of work. It came time to pay. He disappeared with all my work.
Originally, the guy told me he ran a content marketing agency in the UK. I looked it up, traced it back to a company in India. The UK company website was a front. He stole two weeks of my life and work. The biggest lesson I learned from that time.
39 – ‘Nuff said
Here’s a free tip: you can avoid freelance horror stories of your own by reading this one and taking notes.
Don’t work with anybody who says “I’ve got the idea, you write the code, and we will split the money. “
I avoid those situations unless the guy with the idea has loads of money. I mean enough to leave my cushy six-figure job. And they have to be willing to put it in escrow so I can continue to live off it if he bails. Thankfully, that hasn’t happened yet, though there have been discussions.
People think software must be easy because so many phone apps are free.
40 – When admitting the truth is too hard
Some of the most uncomfortable things I’ve found during my time as an accountant has been people embezzling money from where they work.
The worst is when the company owner comes to me with the numbers, and I have to look at them and ask “So, where’d all the money go?” and have them tell me that they have no idea.
Sometimes these owners don’t even realize their employees are ripping them off, and I hate being the bearer of bad news.