I guess this thread could just as easily go in the relationship forum, but I decided to post it here because focusing on the relationship may well be part of the problem. I am in a sticky situation and want to get some other perspectives and suggestions before I act, so please share your thoughts. I am a website designer. I've been doing work for family and friends of the family for several years but because of the close relationship (mother, aunts, uncles, etc), have not required them to stick to the fee schedule on my business website. They basically pay me when the spirit moves them. They know if they went somewhere else they'd have to pay a lot more in a much timelier fashion. It seems kinda sliek because we'll be talking about something else, say a trip to see other family members and they'll tell me how tight their money is and they hope they'll be able to make the trip. Then two or three months later, they'll want me to make extensive updates on their website. Well, I already know their money is tight, so I just do the work, trusting them to pay me when they are able. This is how my uncles' relationship busted up. They were tight partners for decades. They kept very sloppy business records. Then one day one of them decided he was being cheated and demanded they straighten up their act moneywise. After getting a free ride for decades, of course the other brother felt put upon. Specifically, I have been creating and maintaining a site for a family friend who recently sent me what he calls an "incomplete list" of revisions he wants me to make. At first, I started to just do it without saying anything about payment, even though one of the images he wants me to change may involve pixel by pixel color removal. My father told me it's time to ask for what I am worth. This isn't a personal site. This site is for a singing group which they will use to promote and sell their music. He has paid me occasionally, but I haven't kept a record of it. I want to charge him my retainer fee for the last four years since it can be proven that I have been updating this website for at least that long. But without adequate accounting, proving how much of my basic fee he still owes me ($50 a page and $20 per image) might be an uphill battle, so I will just consider it paid . I charge a $60/year retainer fee. so I would be asking him for $240. My problem is, I'm reluctant to do this. I've never down it before. Suppose he knows this and gives me a hard time in the hopes that I will back down? I might not back down. I might feel forced to take his site offline the way I did when my cousin cussed me out in lieu of paying me for his site. My work is stellar. Ask brotha Oldsoul. I know it's worth much more than the money I charge. I just have a problem (call it a hang up, if you will) taking what could risk my relationships with my family and friends. How do I switch gears and start requiring tighter business standards after doing it so sloppoly for years?