Just like financial investments, the riskiest ones have the potential for the biggest pay-off (or biggest loss). My husband of 10 years and I took a big gamble getting together, considering we were both at very different points in our lives and NO ONE thought we should be together (family or friends). But we both went all-in and while things haven't always been hunky-dory we are still happy with our choices. This is from someone who actually preferred to be alone and was always the one who played it safe growing up - so it was all that much more of a risk for me. Overall some of the best things I've done in life are the ones that scared me the most!