This is taken straight from the list explanations of the rolls:
"5)AWESOME! - You must accomplish something really awesome, preferably related to your heir's career or traits, though miscellaneous awesome is allowed. Examples of this include creating a sim bot, putting together a complete gallery of all Egyptian relics, finding and displaying all gems, bugs, or metals in the game, etc. Use your imagination – I'm sure there's something you can find to do. If you're blogging or otherwise writing a story about your sim family, make sure to mention the awesome you got up to."
So it not something in the game play itself, it just doing something extra special.