“If one does not know to which port one is sailing, no wind is favorable.” — Seneca One of the first things I do with a new coaching client is define the destination. Without that, it’s nearly impossible to set a course that actually gets you where you want to go. Sometimes the destination is crystal clear. Early in my career, I knew I wanted to become a public-company General Counsel in the healthcare space. That level of specificity accelerated my path more than I could have predicted. If I were coaching my 35-year-old self, I might have asked a different set of questions. Not just where are you going? but what are you willing to trade to get there? Slowing down to answer that might have changed the journey. Then again, some lessons only stick when you learn them the hard way. Other times, people haven’t really considered the destination at all until I ask. Which brings me back to Seneca. You might arrive somewhere worthwhile by chance. But why leave it to chance? And how would you even know you’re making progress along the way?