I think the best way to live without regret is to not make any bad decisions. What do you mean, "it's not that easy"? Good decisions are made by taking a step back, thinking about the options carefully, and not letting your feelings get too much in the way. Small things are the least to worry about. You can make a bad decision there and not care about the consequences. I've made some bad stock purchases in my life, and those sucked. But I'll live and they don't affect me now. Small. Life decisions aren't so forgiving. How do you pick between your wants and needs when they conflict? Even more confusing are your needs and must haves. To me, there is always the obvious right choice and then the other choice, which is staged by sentiments and feelings. But with enough persuasion, your feelings will learn to accept the "right choice". Or not. But then again, I'm a cold person whose decisions are driven by my brain and not my heart. I don't care about the wishy-washy part.