I have 3 currently, but plan on getting more. I haven't gotten any in about 11 years, because I have a rule for tattoos. If I like the idea/design/location, then I'll sit on it for 6 months. If I still like it, then i'll ink it.
All of mine have meaning. First one is a phrase in Latin related to my military background. Second was on both the instep and outstep of my foot. Just words that remind me a really difficult point in my life and the fact that I came out of it. The last one I designed myself. It's on my right tricep. It's a Roman Legionnaire holding an olive branch and his hand on a sheathed sword. The thought being "search for peace, be ready for war". The outline is in the shape of a shield with an inverse tattoo of the word "virtuoso" on top and on either side of the Legionnaire the words "carpe" and "diem"
Whether or not my kids, or anyone else, one day think they're not cool is irrelevant. They all symbolize one, or multiple, important events or aspects of my life.