Hard to care for the careless

Do you know someone who is careless? They lose things, break things, step in visible piles of dogshit. I find it hard to have sympathy when "bad" things continue to happen to those who are careless, the same thought keeps playing in my head "you need to be careful". I was raised to take care of my things and look out for myself. I know I should feel different and be sympathetic, but it's a struggle. Are you careful or careless? If you're careless, do you find there's a lack of sympathy?