Wolf: “The times I did so in the past have been disastrous and I always felt terrible about it afterwards.”
You should not let your emotions prevent you from doing a mitzvah.
“No one listens to me anyway.”
This is the yeztaer hara talking! Someone once gave me tochacha, and I acted like I could care less at the time (I was 16). But it effected me deep down and played a crucial role in my further development.
“I don’t hold myself to be better than anyone that I’m worthy to give Tochacah.”
This is the yezter hara talking! Shaul was also exceedingly humble, until he was so humble he did not listen to Hashem when he had to be strict and tough. And we all know how his story ended.
“I don’t reach out to people to be friendly – so I’m going to reach out to them to rebuke them?”
Thats horrible, you should be friendly as well. Push with your left hand and bring in with your right hand.