The short answer is that it’s difficult. We must balance living in the world and taking risks with the potential hurt and attachment that results from those risks. Thankfully each of us has an intuitive gut that tends override all conscious or preconscious impulses and remind us how we really feel about things. This is what we become more attuned to in meditation. I like to call it the “true self”. You always know what to do; usually uncertainty is caused by letting the ego or irrational emotions get in the way of your true self.