1) Maybe if you learn this trick people wont think you are a poser anymore. Maybe.
2) Ride towards the obstacle with your feet in the ollie position at a little bit less than a 45 degree angle
3) Pop your board and aim your front truck where you want to get onto the box, rail, rock, log, whatever. Where ever you point your front truck your back will follow. This step is key.
4) Make sure the trucks are securely on so you don't slip off and jack your shins.
5) Ride it out. When your done grinding lift up your front truck and turn it to the side a bit, and like before your back truck will follow.
6) Take the drop. Absorbe the impact. Ride away.