Twenty years from now you will be more disappointed by the things you didn't do than by the ones you did do. So throw off the bowlines, sail away from the safe harbor, catch the trade winds in your sails.
Mark Twain knew what he was saying.
In essence I'd take it to mean to live life by taking chances, with little or no regrets; rather than to simply live and let live carelessly doing whatever.
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Nobody cares about the expensive things you try to brag about online. What really matters, and the only thing people will remember about you when you're dead, is how you treated people and what (if an(How To Make Dress Thoughts)