How much should I tell my children about the mistakes I made when I was growing up?
It is our experience that children (teens particularly) often use your mistakes as license rather than example. We have heard many kids over the years say things like, "Well, my dad did drugs when he was younger and he's fine now." Or "My mom had sex before she got married and she and my dad are happy." We are advocates of telling them you've made mistakes...helps them to not feel pressure to be perfect, but not necessarily being specific. You can always say sentences like "I did some things I regret that I wouldn't want you to have to experience." And then turn the conversation back to them. (If they're teens, that's mostly likely their favorite topic, anyway). The only time it does seem really helpful to a child is if they're in a very broken and shameful place and need to know they're not alone. Then, your words of wisdom and experience feel more like encouragement than a free pass.