Recently, I was pondering upon my relationship status with my IMAM atfs
How will I know how close I am to him or he is to be? How could I check if I am pleasing him or breaking his heart? I don't know. What should I do to become a better individual and serve him?

Strive to be the best follower of him by learning about him and implementing his teachings and those of his forefathers (as). With knowledge comes certainty.