When preparing artwork for an item I like to create a page in Adobe Illustrator that is the precise size of the available imprint area for that particular item. I will then arrange the artwork in that space, save it, then send a pdf file to my client to proof. I always suggest to them that they print it out so that they can see how it will look when printed the exact size on the item. When viewing the pdf on the item it may look great but remember that most of the time it is much larger than how it will be printed on the item. This process is especially important when printing in a small area on an item like a pen, golf ball, lapel pin, etc.

I also suggest following the KISS (Keep It Simple Stupid) philosophy when printing in a small area.