We don’t know how many times he successfully climbed in IMC to get to VFR over the top, but each time he became more comfortable with doing so, and that made it much more likely that some time in the future he would push his luck too far. That moment arrived when the pressure to complete a long-planned trip came up against entrenched low ceilings. When he realized he could not take off the day of his planned departure, he grew more determined to depart the following day. When he could not depart the second day, the pressure became even more intense. Finally, on the third day, the forecast held out the hope of gradually improving conditions later in the day. In a phone call just before he departed, he told his wife he “saw a sunbeam where the clouds were thinner” and that there was a break in the clouds. He also told her that “if I’m not in blue [sky] right away, I’m coming back,” which seems to indicate that somewhere in his pilot brain he realized this was a low-probability exercise.