Choosing a tattoo
First and foremost, always remember that a tattoo is permanent. Yes, with modern technology there are ways to remove a tattoo, but the procedures are generally more painful and more expensive than the original piece of body art you no longer want. You can also find artists who do good cover ups who can cover the old with something new. The best way to not regret a tattoo is to choose a tattoo design carefully.
Consider why you want a tattoo or even a specific tattoo design. Does it symbolize some kind of transition in your life? Whether good or bad, if it's something you want to remember, the tattoo design you pick will be a constant reminder of that specific time period in your life.
Select the location on your body where you want your tattoo. The size and shape of the area can greatly affect the type of design you should choose. For instance, you couldn't place a piece meant to be a full-back mural on your shoulder, obviously you would lose all the detail from shrinking the design so tremendously.
Look through "flash," pictures of tattoo designs, to get ideas. Some people are happy just picking a piece of flash off the wall, but if you want something a little more unique that hasn't already been done many times, then take several pieces of flash and combine them into something new. You can find flash at most tattoo shops, in tattoo magazines at bookstores and tattoo design books.
Get more ideas by searching tattoo designs online. There are tons of websites dedicated to tattoo art, both flash and completed designs that are good examples of what can be done. Tattoo Finder, Tattoo Spot and Tattoo Johnny are just some examples of websites that offer online flash. Some of the sites are free and some you have to pay for the design.
Learn the meaning behind certain designs. Not all tattoo designs have a meaning, but some old school and common designs have a story behind them that might appeal to you or make you decide that design is not right for you.
Pick something that has meaning. Whatever you choose needs to be something you can be happy with for the rest of your life, so if it fits your personality, is a memorial to a lost loved one or something to symbolize your children or other loved one, then you're more likely not to regret it 10 years down the road.
Let your tattoo artist custom design something for you that integrates your ideas and his. This is the best way to truly have a one-of-a-kind piece of body art, because most artists will not give your tattoo to someone else.
Decide on what size you want it and what colors to use. You may go with a simple black and grey design or you may want it to be really bold and stand out with full color.