I have this rule: I tell people how I feel about something once, and then I drop it. By “drop it” I don’t mean I passive aggressively roll my eyes when the topic comes up, or give them knowing little judgey looks. I actually let it go, because that’s their life and I’m currently quite busy living my own.
The key to this is to only give your opinion on something when you’re being asked, and to make it clear that your opinion will be explicit, candid and very blunt. It may hurt. It may suck. It probably won’t be what they want to hear, but you’re not sugar-coating it. You’re not tiptoeing around their feelings. You say what you think, and then you let it go.
We can never really empathize with people completely. We may feel like we’ve been through a similar situation, but it’s never exactly the same. When you’re removed from a situation, it’s okay to give outside, unbiased advice as long as it’s coming from a constructive place. It’s also important to let people make their own mistakes and learn from them.
Nothing teaches you a lesson quite as effectively as falling flat on your face. Even though we want to save the people that we care about from getting hurt, you’re only stifling their growth by holding their hand through life. Sometimes you have to just let go and let people fall off of their bicycle a couple of times. It may sting, but they’ll live and you can hold their hand when you’re helping them off of the ground.