Cha-Ching! Money Talks...but can you ask for it?

When I first started in web design and even to this day, the questions arising about payments, monies due and all those cash transactions always make me nervous and uncomfortable. I don't know whether it's a confidence issue or not but I always seem to cringe when it comes to informing the client about how much they owe me or worse still, following up on a payment that is outstanding!

In some cases I have no problem stating what is due - via email/phone but in person, I tend to be more uncomfortable when discussing money. Usually the client is surprised it costs more than 20 euro in the first place (25 really but hey, who's counting)

I do value my work and I work hard at what I do so I know I work for the money I ask for, yet when it comes down to the crunch I still feel uncomfortable discussing what is owed

Even in personal instances where someone might give me a few euro for fixing a computer or even as a present or something, I always still find it hard to accept money. I guess I just want to do them a good turn and I expect nothing in return! In some cases people even get offended that you don't take their money - but I think they get over it quick enough I suppose if I were asking a friend to fix my tv or car, I would give them money also as a gesture of their time spent on fixing a problem I had, I would expect them to take the money otherwise I guess I would be a bit put out by that too!

So, I guess my question is: How do you ask for money from a client when it's outstanding? What's the best approach when you do feel a bit uncomfortable dealing with these financial situations? Do you have any tips or experiences you would like to share? Are there any pointers you can give to help get over this barrier? Maybe I need to hire someone to handle the cashflow issues? Is that just a cop out?

Thoughts are welcome