The educators who attended the first ever Transition to Retirement: The Uncharted Course workshop did not realize just how significant their role was to be in our now retirement focused world. It was a Pro-D day some ten years ago when we walked into a packed secondary school classroom to deliver our much researched and newly minted workshop. The room was very quiet, yet it was also charged with a current of trepidation, and the expressions on the faces of the attendees were decidedly bleak. These participants were the leading edge of the boomer generation about to step forth into the world of retirement, and that world didn’t look particularly appealing.