Now you may be thinking, why create my own tattoos while I can just get one already created? As I said above, it's better to be unique than wearing an overused tattoo. You can add your own personal touch to your tattoo. Add as much detail as you want to your tattoo as much as you want.
Consider get a tattoo that matches your career, hobbies, and talents, the image you choose will be a reflection of yourself. Consider the reasons why you want the tattoo in the first place. If you want to be expressive or body decoration, think about things that you enjoy or have meaning to you.
In this tutorial, I draw and think in real time, showing how I come up with designs for tattoos. You can see the final version here.
Where Does It Hurt The Most? - Areas of sensitive skin (i.e., inside your elbow) and near bone or cartilage (i.e., on the top of feet & knuckles) tend to hurt the most. Everyone is different.