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  • Writer's picturePatrick Richardson

Setting Your Course in Life and Business: One Lesson From Sailing from a Non-Sailor




As a Creative Director, Managing Director, and High School Mentor, I regularly discuss college and career goals with those I have mentored. One of the most common questions I hear is, “I don’t 100% know what I want to do with my life or career. The answer I give them is a story I heard from a sailor, pirate, or maybe a guy in a bar. Let me be clear: I don’t sail, but this analogy changed the way I think about planning anything. It can be a game-changer for those who don’t know what or where they want to go in their career or life.

Charting You Course: A Sailing Metaphor

Reaching your goals, I tell them, is like sailing a boat. To reach your destination while sailing over the vast ocean, you have to move toward a single point on the horizon while tacking back and forth so your boat stays headed toward your target. Between the wind and the tide, your boat will occasionally shift off course, but your constant adjustments keep it moving toward that single point. In real life, we’re constantly pushed and pulled away from achieving our goals. But as long as we make adjustments along the way and continue to focus on reaching that singular point, we’ll make small progress every day and eventually arrive at a destination near our goal.

The response I often hear from mentees to the response above is, “But I have multiple interests. How can I head in just one direction?" From there, we discuss their interests and see where those interests overlap. A student who is interested in art, history, and music, could be happy working in a museum or a music hall. By clustering the things you like, you can move in a direction toward a few of them.

The last bit of the analogy is this: The ocean is massive, so it is going to take you a very long time to get to where you want to go. The trick is to get started immediately because you will likely want to change course and pivot and head toward a new direction soon after starting. But if you never leave the shore, you are going to be less experienced and that much farther away from your new dreams. 

Following Your Path in the Business World

Finding that point on the horizon is essential in business as well. We often work with clients who have big ideas. One of them, a medical doctor, wrote a best-selling book to help people transform their health. After proving the concepts in the book were effective at helping people lose weight, he wanted to turn his ideas from the book into a mobile app. 

Following that point on the horizon required significant tacking through our conversations. We had to decide which concepts from the book to keep on our journey and which concepts we needed to throw overboard because they didn’t translate well into a digital tool for tracking health. Over time, we adjusted our course and eventually reached our destination with a mobile app. 

Our plan for the app was fluid. We allowed for conversations, deviations, and new ideas to influence the final outcome. Resisting these interruptions is generally bad for any project. If we insist on sticking to a “perfect” or “ideal” plan, we miss some of the opportunities that arise organically over time. Remember: You can’t sail without wind, and you can’t make significant progress in business by working in a vacuum.

This same sentiment is true on team projects. Some projects, like mobile app development, rarely go according to plan. Changes sparked by team discussion and evolving project needs can be good. We should take what we learn from our team, the creative process, and our own professional growth to inform our next decision. As long as we’re moving toward that point on the horizon, we’re making progress. 

Tacking For Success

Reaching our goals is challenging, but we can make the process easier on ourselves. By determining a general direction we would like to head and jumping in the boat and setting sail. There will be tons of course corrections along the way, some rough seas, and some splendid sunsets. And take it from a guy who has been there: Sometimes you get to your destination and can’t wait to jump back in the boat and head off for another adventure

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