Regret vs risk, what side of the issue are you on?

Given the chance what side of the fence would you rather be on, having taken risk and maybe lost big or playing it safe and wondering if you missed out on great experiences or rewards because you never took a risk not forced upon you? If you never take risk to avoid falling deep into a pit or suffering behind something will you end up regretting that fact when you get old because now it is too late to go back and do or change some of those things you passed up on earlier in life? I once heard a phrase that said it is better to be a has been or a never was.