I work in the interior home industry.

Colleague: Hey, can you produce this custom artwork for my own personal home?

Me: Not really. This isn't customer-paying work and I can't do private jobs during working hours. We're also super busy with paying jobs at the moment and already have weeks of overtime ahead of us. If you like, though, you're welcome to contact me outside of work and I can send you a quote.

The colleague emails details over, doesn't like the very modest quote provided, and decides not to proceed. No worries.

The next day in the office...

Colleague: Great news! I went direct to our CEO, who's agreed to let you do this on company time! I only have to pay them half what you quoted me this way! Amazing, right?

Me: *Internally* Yeah, amazing... You've done this knowing full well you're adding to my overtime. Plus, our work hourly rate means I won't be compensated properly for the personal time I need to spend on this. So happy for you.

Fortunately, I was able to speak to the CEO and got this job canceled due to an already over-stretched workload. I have no idea why this colleague thought I would be happy about being paid less for the same work.

I do software development and have a lot of experience dealing with databases and handling multimedia. I have a friend who wants to build a social network mobile app and has come to me for advice.

Friend: Could you build me a sample backend so I can see how it's done?

Me: Sure! I can do that!

The initial backend isn't too hard and doesn't take too much time, but as anyone knows that wasn't the end of that...

Begin loop:

Friend: Could you add [feature]?

Me (begrudgingly): Sure. Can do.

End loop.

Eventually, I start not focusing as much on it because I'm in school and my classes are taking up more time than I expect. After a while, I follow up about it.

Me: Are you still needing me to implement [features]?

Friend: No, we haven't we decided not to work on the database side of things anymore, sorry, thanks for your help though!

To be honest, I was glad to not be involved anymore. Especially when I saw the finished result. Some of the highlights:

Passwords sent over HTTP and not HTTPS (not hard anymore to fix), Potential COPPA violations. The website was a static HTML page. WordPress isn't that hard to set up.

Oh, I forgot the best part: my friend was a computer science major at the same university I went to. He also took the same classes I did and should've been able to do what I did.

I'm a freelancer doing a website for this couple. I did the wife's website first three years ago when she asked me to help her because her website was down, the thing is she just forgot to pay her server, charged her really low because we're good friends. Everything was good, I gave her all her log-in details, told her to change her password, etc.

Two years ago the husband asked me to do three websites for him. The husband choose a host server that I had never heard of before, and he did it without consulting or asking advice. It was a confusing server to work with and required a lot of customization to get what he wanted. I managed to finish the websites. I remind him if there are changes required to the website then let me know first. All is good, and I am paid. Again, I charge less because we're good friends.

For the third website, he asks me to make an "NGO" website. I make a demo on my own server to show him if he likes it. He doesn't make any payment and I don't hear from him for a couple of months. All of a sudden he emails me to meet because he moved his domain to another server that I never heard off, again without notifying me, so I didn't have time to make an updated backup. There's an error on the first website and I can't work with the confusing host server so I tell him to find somebody else, and I will give him all the content and the old backup that I have.

He agrees and emails me to send the backup to the new web developer, which I do. He emails again asking for the demo website. I politely tell him that I did the demo and it's there's very little left to do, so if he wants it he has to pay: half of the full price, because who would just give something they did for countless hours for free so their new web developer can just upload it to their server and get paid?

He finds my rate too high apparently, so he starts asking "didn't I get paid already per hour?". Just to be clear, the first two websites were paid for the whole website. I politely tell him that he was not paying me for the hour but he's insisting on how much should I charge per hour. I again reply that I don't charge per hour but charge for the whole website.

Then, he asks me if I'm paying taxes. I don't reply because I have no obligation to tell people - even clients - regarding my personal finances, etc. He emails me again insisting to answer him so can I come up with what he considers a "lump sum" of money but only if he knows who is paying taxes. I still do not reply.

Then here comes the threat: If I don't want to answer him, I will answer one way or another because he will report me for tax fraud; seems like extortion to get my demo for free. I block him and his wife on social media, and all of a sudden the wife's website is down. Instead of emailing me her issue, she goes on Facebook and accuses me and my boyfriend of blocking her website. Like I'm really gonna waste my time anymore on their websites?

And BTW, if you're website is down why don't you contact your host provider first, maybe you forgot to pay again...

I get a message from a family friend:

Client: I need this logo, and it should be really, really easy. Can you do it?

Me: Sure, send me the details.

Client: It's going to be embroidered on a hat. I want it to have a bench and a tree and rocks on both sides of the bench and a flag in the background and gradients and grass. I've made a sketch. 

It's a VERY detailed sketch. Done small, embroidered, it would look a mess. 

Me: ...and all of this is going on a hat... embroidered?

Client: Yeah! 

Me: It'll probably look better if we make it a little simpler. This isn't going to work well for what you want. 

Client: Thanks! When can you have it done?

I decide to let it be their problem. 

Me: ...next week?

Client: That long? OK, it'll be fine, I guess... 

I send it over, based on the drawing. I ask for feedback. Three weeks pass.

Client: Sorry, I've been busy. Why is the bench so short? Why are the rocks so large? The flag needs to be a triangle. I don't want grass. Can you get it done quickly? 

Everything looked like the sketch. But I make changes. Another three weeks pass.

Client: I didn't see this until now. The flag needs to be a rectangle and bigger, and change the colours to something less obnoxious. The bench needs to be shorter and the rocks larger. Why are they so small? Where's the grass?

I make changes. Again. Two weeks pass. 

Client: When will you be done?

Me: I already sent it.

Client: Oh right! Just take away the flag. The grass must be taller. Can you change the colour of the bench to red, and the grass to a more autumn-yellow and can you make it look like the grass is blowing in the breeze? And the rocks should be more of a green-grey than a grey-grey, and three more shades on each would be cool. 

This basically went on for about three months. By which time it felt like pulling all my teeth at once.

I never saw evidence of a hat. Probably because they realised it didn't work.

A friend of mine texted me (she's an actor) saying to call her, because she has a "job" for me. Turns out she's an ensemble member in a theater, and the theater needs a new corporate design, which is my specialty.

Yeah, it would be paid, there's money available, just, just, just - the way they wanted to handle it is they were going to ask a bunch of freelancers and agencies ("just a few") to submit "a few" (of course unpaid) ideas and drafts and then will decide with whom to work.

I had to explain to her what "no spec" means, and what the idea behind a designer's portfolio is. She insisted:

Client: That's the way it's done in business.

She based this on the fact that she once worked in an agency for 3 months, 20 years ago. I had to explain to her that yes, pitching is a thing but that 1) it's something agencies (not freelancers) do for 2) bigger budget projects than this and that they 3) get paid for the pitch.

She kinda gave in a little, but already just another piece of evidence why you should avoid working for clients that are from your friend circles.

I got a website project from a friend of a friend. His "business" was in door-to-door sales. There were plenty of red flags indicating this guy was going to be a nightmare to work with, but against better judgment I took the job.

A few weeks and way too many revisions later:

Me: The site is done. Once you pay me I'll get your hosting set up.

Client: You're charging this much? My cousin would do it for way cheaper

Me: This was my agreed-upon rate from the beginning. If you can get a better deal I encourage you to do that, but I do need to be paid for my time thus far. 

He paid me, begrudgingly, but opted to hire his cousin for the rest of the job. I sent him the code and files. Job done, clean break. Could be worse. 

Six months later I got an email:

Client: Hey! This is my cousin. Please help him set up the website.

Me: ...I'm sorry. I'm not taking on any new projects.

At which point he lost his s***. 

Client: You have an obligation to help me! The job isn't finished!

As if I should take the time to teach this guy's incredible cousin how to set up a website, no charge, six months later. 

Luckily I had a contract to fall back on. Pretty much just shoved the files back in his face and wished him good luck. I did end up walking the cousin through a few things out of totally feeling sorry for him. But even that was in vain. He truly had no idea what he had gotten himself into. On the plus side, he was "super cheap."

I'm an industrial and interior designer. For a client's research project, I designed and built an interactive installation, with VR and physical interactions. Everything went quite well for this part, but at the end when I offered to create promotional content (high-quality photos and videos), the client told me there was no more budget, and asked me if I could still create the content.

Client: I have no research budget for the photos and videos. Can you still do it?

Me: Well... I have to do it for my portfolio anyway... But it's going to be more "modest" than what I would have done with budget, and it's going to be focused for my personal use. But I can share the content with you once it's done!

Client: OK! I just need it for my PhD defense. 

Me: OK! If you don't mind I will ask you to pay the costs 50-50 with me. So just like 80$ to pay a photographer friend a little bit and rent some additional filming equipment. He will bring his cameras for free and we will be the models in the videos and photos.

We did everything and ended up with good footage and photos, which I shared with her right away.

Three weeks later:

Client: Hey! So, is the video done? I need it in 3 months.

Me: Well, it's not. I am sorry, but the thing is... I learned that I have cancer. So I will not be able to edit the footage and make a quality video. I need to focus on my health. But I can refer you a friend to help you with the video, it's due in 3 months, it's really doable.

Client: Oh, I'm sorry to hear that! But you put me in trouble, you know. I don't have any money to pay your friend. You told me you could make the video. I was relying on you!

Me: Well, like I said, I have CANCER. 

Client: I know and I am really sorry for you and wish you the best, BUT... When I tell someone I can do something for them, I try to be true to my word...

Me: Well... How long do you want your video?

Client: 10 minutes.

Me: What? Sorry, it won't be possible and I think there was a misunderstanding. I offered to share a video I would do for MYSELF, for my portfolio. Something 1 minute long, max. You can't possibly think that for $80, you would get professional quality photos and footage, and get me to work like 20 hours to make a professional 10 minute video, right? Already, you got the content and you paid practically nothing for it.

Client: WHAT? I paid nothing? I paid $80 and you told me you would make me a video! I was there for 4 hours when you filmed and took photos. I modeled. I worked and helped you, you know, it's worth something! 

Me: I was there as well, directing the video without a scenario because you couldn't pay me to prepare one. I was there for more than 4 hours, and managed everything. And... I HAVE CANCER, REMEMBER?

Client: If I knew you would drop me like that, I would just have taken pictures and videos with my iPhone.

What. The. Hell. 

I’m a music producer. I was working with a friend to produce a song he wrote, and I did it for a HUGE discount because he’s my friend, he’s moving away soon, and I’m still building my portfolio. Big mistake. 

After I sent him what I thought was the final mix

Client: Can you bring the bass down slightly? Just a tad.

Me: (makes changes and sends it to him)

Client: Can you pan the rhythm guitar to the left and the lead guitar to the right? Also lower the bass a TINY bit. And can you BARELY lower the vocal effect volume?

Me: (makes changes and sends them to him)

Client: Actually I was wrong, the bass is too quiet. Can you bring it up just a TINY bit? Also I don’t know why you panned the rhythm guitar, can you center it?

Me:  You just told me you wanted the rhythm guitar panned. Also, we’ve been making tiny revisions like this for a month, so if you have any more tweaks you want me to make, these will have to be the final ones because I have dress rehearsals all this week for a show I’m in, and won’t be able to work on your song. I think the mix sounds great.

Client: Since I’m paying you, I want to have the option to make more revisions if I’m not 100% happy with the mix.

Me: (angrily stays up late making changes, sends them to him)

The last straw was when he texted me right as a show I was working on began its opening night.

Client: I don’t like how there’s no rhythm guitar in the intro. Can you copy and paste the rhythm guitar from the outro into the intro? Also I need this done by the end of today, I really want to release this song this weekend.

Lessons learned: don’t give your friends discounts, and for the love of God, charge extra for ridiculous amounts of revisions.

This one time a childhood friend of mine asked me to photograph an event. Since she was a close friend, I agreed to do it for free before really thinking about it.

I wound up having to cut a vacation short to do it, but I’d given my word. I rebooked my return flight so I arrived just in time to cover the event. I showed up, took about 400 photos, and then went home and fell right asleep because I hadn’t slept in over 20 hours and had gone straight from a long flight to covering this event.  

The next morning I woke up to a Facebook message:

Client: Why haven’t you sent me the photos yet?

Me: I still need to process them! It will take a few hours and I was asleep.

Client: Well by when can you do it? I need to post the photos on Facebook now!

Me: I would say about a week but if you are in such a hurry I can look through them, choose some standouts, edit them and send them to you tonight.

Client: No, I need them all now.

Me: You wanted these edited. I can’t edit 400 photos in one night.

Client: But I need them all now!

Me: Sorry but that’s impossible.

Client: Well then don’t edit them all, just do, like, half of them.

Me: That still takes more than an evening for me, especially since I am busy with my day job besides. Best I can do is 4 days.

Client: Okay.

Half a day later:

Client: Why haven’t you sent me the photos yet?

I just ignored the message. The next day:

Client: Why haven’t you sent me the photos yet?

I hurried to do something and sent her roughly 40 edited photos and another 250 unedited. She was still complaining I was late and ended up posting badly over-filtered versions everywhere.

She didn’t say “thank you” once.