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.
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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! :)