Preheat your panini press. Spread each sandwich half with Dijon mustard. Divide the ham, cheddar, and pear onto 4 sandwich halves. Place the remaining sandwich halves on top. Brush each the bread lightly with olive oil (on both sides) and place two sandwiches on the panini press.
Grill for 3 to 4 minutes or until the bread is golden and the cheese is melted and gooey. Cut in halves and serve with an arugula salad and extra Dijon mustard.