About this episode

The episode discusses the parallels between sailing upwind and leadership challenges.

Lessons in Sailing Upwind William D. Parker, July 9, 2026 When my friend Dave Sandowich, a retired principal with 20+ years of admin experience, invited me to go sailing with me off the Chesapeake Bay, I was thrilled. This would be the third time he had taken me on the water, and my son Jack, now 20 years old, was coming along. We sailed 60 miles over three days, from Dave’s place on Kent Island to Annapolis, Maryland, and then south to a quiet cove. Sailing upwind was the most challenging and exhilarating part of the trip. Calm waters and quiet moments were nice too, but Dave was quick to point out that sailing upwind takes work – a mastery of understanding the sail and jib, the use of crewmates to help you come about, and knowledge and skill to stay on track. As Dave told me the first time we sailed together in 2019, “Sailing is a lot like leadership,” he said. “On a sailboat your destination may be directly from where the wind is coming from. A sailboat can’t sail directly into the wind but it can work its way up wind by sailing at angles off the wind and working its  way up wind to the destination. It is more work and will take more time but you will get there if…

People in this episode

Host: William D. Parker

Guest: Jen Schwanke

Topics covered

• leadership
• sailing
• personal development
• teamwork
• resilience

Mentioned in this episode

Books & works: MONDAY MATTERS

Places: Chesapeake Bay, Kent Island, Annapolis, Maryland

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