Ash is ten... why in hell would he just stop chasing is dream? Besides he already saw some many amazing things that even i wouldn't stop. And 44 badges, many respectable positions in the pokemon league, winning the kanto battle frontier and orange league championships is not silly for a guy that hasn't achieved puberty is not silly at all.
Also he has been cursed by a rotting disease since the beggining of the series: marketing. It's not his fault. He may have luck sometimes but the majority of the things he gains was his doing and not fate. He's hardly the luckiest guy in the world ( EXEMPLE: trollbias)