Getting a tattoo over scars is easier said than done - it very much depends on the scars you have, how deep etc.. Make sure you go to someone who knows what they are doing and has experience tattooing over scars. Scars make for much tougher skin, so getting the ink accepted and getting clear lines etc. may be difficult so you may need extra sessions.
I have a tattoo on my wrist, not over scars, and I have noticed that a lot of public sector jobs and teaching have asked about tattoos. Definitely make sure that a shirt can cover it however, as 1 in 5 people have tattoos the attitude should change but be aware that it very much depends on the other person sitting on the opposite side of the desk. Some people are old school and frown on it. I don't regret my tattoo, if I am honest I've had it for so long it is no different to having a freckle there, you get used to it..
Also, be prepared to show pictures of it and explain the meaning. One of my job interviews asked for a photo of any tattoos.