Taking the Indirect Route

Leadership often requires moving forward when conditions push against you. Like a sailboat captain navigating a headwind, Best Bosses rarely take a straight path to their destination.

Years ago, I traveled to San Francisco with a group of interns. One afternoon, we boarded a 51-foot Morgan ketch to sail the bay. While others enjoyed the views, I found my way to the captain.

She taught me about the various sails—the mainsail, the mizzen, the jib, and the staysail—and about how the rudder, keel, and helm worked.

Curious, I asked her how we were moving forward despite sailing into the wind. My mental model—shaped by movies—assumed progress only came when the wind was at your back.

She smiled and introduced me to a different reality.

“We’re tacking,” she said.

Instead of sailing directly into the wind, the boat moved at an angle. The sails caught the wind in a way that generated lift, pulling us forward. Beneath the surface, the keel provided stability, resisting sideways drift. Then, at the right moment, the captain adjusted the sails, shifted direction, and repeated the process—zig-zagging toward the destination.

Progress wasn’t linear. But it was intentional.

That day reframed how I think about leadership.

Best Bosses don’t fight headwinds with brute force. They work with them. They recognize that resistance often requires an indirect route—one defined by adjustment, patience, and disciplined course correction.

Stay on one heading too long, and you drift off course. Adjust too frequently without direction, and you lose momentum. Leadership, like sailing, is a balance.

Vision sets the destination.

Strategy sets the angles.

Leadership is the discipline to keep adjusting.

The wind doesn’t have to change for you to move forward.

You just need to choose the right strategy.