I think the biggest thing I have tried to do is just to say yes more. Not so much at my job because people just tend to ask for stupid things, but in my personal life for sure. When my wife or friends want to do or try new things, I don't want to be so hesitant about it. It's a work in progress!
Sometimes people over-thknk things and cause themselves to miss out on good experiences I guess. Sometimes it's good to just go ahead and do it though. It'll be good or bad, but either way is an experience.
I tend to like to play it safe and I need to stop worrying about all the things that could go wrong all the time.
I don't have a problem with a degree of caution, that's sensible, however making calculated decisions can also pay dividends. Risk/Reward, one must always weigh it up.
I'm still trying to sort all that out! :)