Become More Ambitious
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While it is a great act of kindness to try to encourage people who appreciate your words, they can be a source of great irritation if you try to encourage people who don't want your encouragement.
Even if your intentions are entirely for that person's welfare and benefit, if a person you want to encourage becomes annoyed by what you are saying, it is a bigger act of kindness not to say anything.
Some people might feel okay if you speak concisely and to the point. But lengthy encouraging speeches might be a source of irritation and distress.
There is a valuable rule when it comes to communication: The results show the meaning of your communication. You might want to be helpful but if that person feels uncomfortable because of your words, it transforms something meant to be positive into something negative. Then what you meant as an act of kindness is actually the opposite.