"Your success in life is largely dependent on how many uncomfortable conversations you're willing to have."

My former boss told me this when I was denied re-enrollment to my university to finish my degree. He encouraged me to take a day off from work, drive down to the university, and negotiate with them in person about the ordeal. Being a very non-confrontational person, I would never have done this on my own. Sure enough, I spoke to the offices about it and I was able to enroll.

He later used this line again when he had to lay me off because of financial constraints. But thanks to the same advice, I was planning on leaving work anyways to attend school full time.