Life-Long Lessons I Learned from Sailing

sailing team on the ocean racing a sailboat

Ever since my father first introduced me to sailing as a youth, the simple joys of sailing emerged from the newness of each experience. I grew up sailing on Lake Walloon in Michigan when every taste was new, the wind was alive and every vision unique. This was a time when I was learning about the world, and sailing came as a blinding rush that melted into endless revelation. Some never get to experience this joy, but for those who do inevitably fall in love with the sport. Through this simple introduction to sailing, my father taught me some of the most important life-long lessons for living a bold life.

“A sailor is an artist whose medium is the wind.” – Webb Chiles

I remain an avid sailor, and with each new season, sailing rejuvenates me. To sail is to experience the world, to experience nature and experience a re-birth of the human spirit. The world comes alive as the tiller attaches to the vessel, and with each dip and wallow of the boat, senses come alive. There’s the wind in your face, the smell of fresh air, the rock of the boat and yet, despite all this, a tranquility in the sport. Also, a big part of sailing is the community or social aspect it provides.

Here are four important life lessons I’ve learned from sailing:

1. The Path from Point A to Point B is Rarely Linear

One of the first things you learn when sailing is that you can’t always get from one mark to the next in a direct line. If your desired endpoint is upwind, you have to navigate to an alternative point for a length of time before pointing back to your goal—this maneuver is called a tack.

There are parallels to this in business and in personal life. It is a rare occasion when one’s goals are easy to attain and come in a quick straight line.

As Robert Frost famously wrote, “Two roads diverged in a wood, and I—I took the one less traveled by, and that has made all the difference.” In sailing, often taking the course less traveled results in winning the race. Such strategic planning in life or career offers the same effect.

2. Big Things are Measured in Small Increments

One of the biggest lessons I have learned from sailing is that the little things matter the most. For sailors, understanding the intricacies of tying a knot, when to tack, or how to read the wind are crucial to safe and successful outcomes.

There are many different knots used for many reasons. For instance, the bowline is often considered the most important of any knot and has been used by sailors for over 500 years. It is useful because it can be tied around a post or any fixed object, and under pressure it tightens and will not give away. Knowing how to tie this knot and do it quickly can make the difference between your boat unintendedly breaking away from a cleat or your jib sheet breaking away.

When sailing, one of the first lessons is how to read the wind and the impact it has on direction, speed, and safety. A sailor learns to understand wind shifts and to watch the thin pieces of yarn on halyards (line used to hoist the sail) that indicate a change in the wind. If during a race you fail to accurately judge a wind shift or fail to adjust promptly, you may lose the track, or worse, the boom (bottom of sail) can swing around violently and knock into the crew.

Just as in sailing, life takes a similar course. It is the little things that matter most. This is important whether its understanding the needs of your loved ones, reading your customer or building a new product. Those who are successful in life understand how to read the signs and make the appropriate adjustments.

3. It is not the Captain Who Wins but the Crew

john miles sailing with this team

Yes, it is imperative to have a great skipper, but unless that person is sailing solo, they cannot win the race on their own. On a competitive crew, there are many different responsibilities demanded of the team. Some of these roles include the helmsman (most often the skipper), mainsheet trimmer, cockpit, jib/spinnaker trimmer, and tactician.

The team must work together in unison to properly sail the boat in a quick and precise manner. For instance, the mainsheet trimmer is responsible for working very closely with the helmsman to maintain boat speed.

The cockpit or pit person is responsible for organizing and maintaining all the lines leading to and from the cockpit on the boat. One of my favorite skippers told me that an excellent cockpit crew makes the rest of the ship look great. This is because this position must communicate and coordinate the hoisting and dropping of the spinnaker between the cockpit and the foredeck (front of the boat).

Similar to life, it is your family or team environment at work that makes the difference. As I learned as a plebe at the Naval Academy, there is no “I” in team.

4. It is Easy to Give Up—It is the Strong who Persevere

One of the biggest lessons I have learned from sailing is how to persevere against the odds. Last Fall, I was sailing with my regular team on a Melges 24. We were leading the race series but in this individual race we had made some tactical errors and found ourselves over a mile behind the leader heading into the first mark.

Instead of giving up and just handing over the race, the team talked and came up with a new strategy. We took a much different path on the next leg and made up ¾ of the difference. By the time we rounded the 4th mark, we were a quarter mile ahead and ended up winning the race by nearly a half a mile.

Similar to life, it is easy to give up in the face of obstacles or what look to be insurmountable odds. Like a sailor, we often do not have control of the way the wind is blowing, or where our life is heading. What is important is not to complain, make appropriate adjustments and make the most of the hand you have been dealt. I have often found that it is the most successful people in life and in business who are not afraid of what they cannot control.


There are many lessons sailing has taught me and continues to teach me with each passing year. However, the most important lesson I learned from sailing is to make the most out of whatever situation you are in— and figure out a way to succeed.

Previous ArticleNext Article
John R. Miles is EVP, Business Development and Associate Publisher for Bold Business. He is a veteran, thought leader and strategist of what makes great companies tick and their impact on society. He works as an advisor to many of the world's largest influencers and companies to create tools and solutions to tackle our most complex global challenges. He has spent over 20 years working around the globe at the intersection of business, social, technology and security issues as a CEO, Publisher, F100 CISO and Fortune 40 CIO. John has written over a hundred articles on topics ranging from health, big data, digital transformation, urbanization, nutrition, the blue economy, transportation, and cybersecurity.

Leave a Reply

Your email address will not be published.

two × 1 =

Send this to a friend