Is the leader born with the skills of statesmanship, or else what is the source of the expertise and theoretical knowledge that the statesman puts into practice in ruling over people? In the opening part of The Statesman, Plato takes us back in time to the beginning of the universe to search for the leader class and asks if there is in fact any natural separation between the ruler and ruled. Members of the Toronto Philosophy and Calgary Philosophy Meetup groups considered the question on April 24, 2022 in the first of three meetings on Plato’s Statesman. We began with own journey in time to listen to a statesman and found the words of Robert Kennedy’s 1966 “Ripple of Hope” speech still have the power to stir the soul’s spirit as much as they did half a century ago. In Plato’s dialogue, the Visitor from Elea likens statesmen to herdsmen who apply the force of their minds to direct the souls of their followers and thereby shape the arc of history when confronted by multiple choices and probabilities. In our dialogue, we explored the problem in the division of differing perspectives as we navigate the course of time. That the challenge might not always be resolved by rational calculation is a foundational principle that we can consider in our next session on The Statesman, in which the Visitor holds the job of the statesman is to find the mean of extremes. In the polarized politics of our time, use of the imagination may be the key to finding the mean where human potential can exceed either of two extremes. The many fascinating thoughts raised in our discussion certainly demonstrated the potential of moving beyond the limits of “what is” to “what if”, as one participant stated most powerfully.