Whether it’s a promotion or a pivot, a great pitch or a stroke of luck, behind most successful careers is an improbable jump that unlocks new possibilities. Ryan Seacrest went from small-time broadcast host to breaking big with American Idol. On the other hand, Rob Reilly, the Chief Creative Officer of WPP, shocked his colleagues when he stepped backwards just as his career was about to peak, and IPG’s Jacki Kelley made some moves that surprised even herself. Plus, radio and podcast personality Angela Yee and advertising executive Tim Castree have amazing tales to tell about climbing the ladder and making a name for yourself.