Without regrets

A friend of mine told me this recently that I should live my life without regrets but why does one mean by living life without regrets? Does it mean that I should let it all go, throw cautions and hesitation to the wind? I must say in my life there are many things I regret because either I was too careful or took too long to think or perhaps purely afraid of taking the risk. What should I do ? Should I change ? Does changing makes me a better person ? In due time I'll see. However it's hard changing ones thinking and behavior after all been doing it for so long.