What is your biggest regret as a parent? What is an accomplishment that you are proudest of? For me, my biggest regrets are having both of my boys circumcised, I just didn't know then what I know now and giving up breastfeeding with my oldest after only 3 weeks. My proudest accomplishment is breastfeeding my middle child until he was 3 1/2 years old, despite the judgement from my husbands side of the family.