Lasting teshuvah and personality improvement only occur through heavy duty internal work, and that always causes pain.  Bad habits, bad middos, and aveiros change how you think and react – and undoing that is uncomfortable. 

Discussion of the Gemara’s insistence that a person try to avoid speaking about disastrous events directly.  Nuances in the prohibition to relay that a person has died.

Citations: In addition to the commentary of the Vilna Gaon on Mishlei, this shiur references Gemara Pesachim 3b with commentators Rashi, Bais HaMechira and Chasam Sofer, and Shulchan Aruch Yoreh De’ah 402:12, Teshuvos Mahari Veil  - 13^th siman, Teshuvos Rav Azriel Hildesheimer 1^st chelek, 263^rd siman.