To fly a job, click on any airport on the map, then click Job's board on the right, and look for one which involves passengers. To frighten the passenger during the job, you must get the green tick on the right to turn into a red exclamation mark. A simple way of doing this is either to perform aerobatics in flight or point the nose at the ground to make them think they are going to crash, then pull out at the last second and complete the flight. While most jobs require a larger plane like the Maule, the $100 hamburger can be completed in the icon, however, it will take 10 of these for the achievement to unlock as you can only take 1 passenger at once.

~Int