Leadership sailing

Moving Forward – Stay Close to the Wind

I have been a passionate boater since junior high school. My first boat was an 8-foot sloop with one sail. Every weekend, I would go to Marina del Rey, carry the boat to a slip, raise the sail, and head out.

As I got older, I discovered power boats. You turn on the engine and go. No need to work hard pulling up the sails to go 5 miles per hour. Just turn the engine on and I could travel at 30 mph.

Yet recently, my passion for sailing has resurfaced. I have had the honor of sailing with my friend Bill on his 42 foot Catalina sailboat. I discovered the magic of quiet and the challenge of “staying close to the wind” to move the boat forward. Yet, to “stay close to the wind” you need to constantly watch the wind, trim the sails, and work the winches. The result is moving forward.

To stay on course requires continuous adjustment to the changing direction and velocity of the wind.  All of us have an ongoing opportunity to “stay close to the wind” or to continue adjusting our behavior, thinking, and perspective so we continue to move towards the accomplishment of important goals.

Staying close to the wind takes effort.

Keeping the momentum to reach a goal takes effort.

In physics, a fundamental principle is “a body at rest will stay at rest and a body in motion will stay in motion unless acted upon by an outside force.” Staying close to the wind requires that you stay in motion.

So, how do you “stay close to the wind” and continue forward momentum? Here are five tactics to help you.

  1. Make a Decision. Erik Erickson was a deep thinker on adult life stages. He believed each stage of life involves a crisis. A person must decide to resolve the crisis or not. One crisis is called “generativity versus stagnation.” This decision is between “staying stuck” or “making your mark.” The decision is yours.
  2. Stop to Start. It sounds counter-intuitive, but I challenge you to discipline yourself to stop. Like parentheses in the middle of a sentence, you need to find quiet space between the urgencies of your life. During that time, think about ways you can “trim the sails” of your life. Ask yourself “What is holding me back and what can I do about it? And the most difficult question is “What do I want?”
  3. Fail Often. To move forward you need to fail. If you are not failing you are not really trying. Staying safe is stagnation. Like sailing, if you are not open to trim the sails to a point the boat begins to “luff” or slow down. Then you are not truly pushing as close to the wind as possible.
  4. The Extra 30Minutes. Whenever you are about to stop or quit, take an additional 30 minutes and keep working. Yes, keep working. You will be amazed at how the momentum of your life continues.
  5. The Power of Incubation. Plan your day the day before. Put into your schedule your tasks, daily goals, and appointments. Allow incubation to occur through the night. This means that when sleeping your unconscious mind will be “trimming” your priorities and even providing you new ideas.


“Staying close to the wind” means understanding the currents that keep your business or career on course.

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