
Last Friday I went sailing on a boat like the one above and it was fantastic.
My friend Bill emailed me Wednesday evening with an invite. Turned out to be a perfect day, a little fog in the morning that burned off for a sunny afternoon. I loved every minute of it.
(Here’s a bonus tip for you before this post sets sail. On a previous occasion I made it clear that, due to my flexible schedule, it was possible I could be available at a moment’s notice for a sailing trip. Thus the invite. The point: Say what you want.)
Reflecting on my experience over the weekend, I realized that sailing is a great metaphor for success in life.
Here are eight tips for sailing to success.
1. Be Shipshape
A boat that has been neglected could result in a miserable, potentially fatal, experience.
Hull integrity is necessary to keep the boat floating. A working motor allows for piloting in and out of a dock, as well as the ability to keep moving in a dead calm. Sails and lines in good condition are a must for sailing, period.
In the same way, your physical body is the vehicle for your journey, with the same risks of neglect.
Whether you are planning a new direction in life or well on your way, take stock of your current physical condition.
Do you need to change the quality or quantity of your diet? How’s your level of exercise? Any health issues that you’re putting off or not attending to?
Here are three easy steps to shape up:
- Walk 30 minutes three times a week.
- Eat less food and drink more water.
- Get up to date on all medical checkups.
2. Know Why You Are Sailing
Last Friday, all I knew was that we were sailing out into the Bay. Since my goal was the experience of sailing, not reaching a specific destination, that was all I needed.
If I were to buy my own boat and sail regularly, I’d start to develop goals for each outing. I might want to learn and practice a new skill, entertain friends or to have lunch over on St. Michael’s. Knowing my purpose before sailing would allow me to take action toward my goal.
As I work with men to bring more passion and purpose into their lives, it’s common to hear them talk about wanting to make a change but not have an end result defined.
Having definite goals is a must for success. Goals can be small or large, for long-term change or brief stops on the way to the next goal.
Use these three questions to begin to plot your course:
- What are the feelings you want to have when you reach your goal?
- What conditions need to exist to provide those feelings?
- What do you need to do to create those conditions in your life?
3. Sail With A Crew (And An Experienced Crew Is Even Better)
Even though I didn’t know the first thing about sailing, my friend has twenty years of experience on the water. As a result, he could take care of all sailing tasks and include me as he determined was wise. This also allowed him some different options, such as heading out to the prow to sightsee while I was at the helm.
It’s easy to assume you have to learn how to do everything well. Easy to forget that the structure of our economy is to pay someone else for something you want but don’t do (or want to do) personally.
Adding people to your life that can join and assist you on our path to success provides support, knowledge, experience and skills that you need.
Ask these three questions to staff your ship:
- Who do you know that has the experience you lack?
- Where can you find professionals that can assist you in the remaining areas?
- What tasks can you turn over to someone else?
4. Question The Captain
I definitely know much more about sailing today than I did last Friday morning.
During our time on the water, I continually asked questions about sailing. I learned about the names of different types of boats and how they’re different, how to adjust the sail to catch the wind, how the length of the boat relates to its top speed and how to read the various buoys and markers.
When you find experienced people on your path, try to find out what you can. Prioritize and ask your two most important questions and, if they’re open, ask even more.
We’ve all heard the saying ‘the only stupid question is the one not asked.’
Question yourself and others to quickly move up through the ranks:
- What are the strengths of my plan?
- What are the weaknesses of my plan?
- What am I missing?
5. Follow The Markers
There are a number of marker, buoys and lighthouse on the water to guide sailors to safety.
Certain buoys mark places where shoals jut out into the water, where a boat could run aground. Some have green or red lights on them, to guide a boat moving in or out of an inlet. (On the way out, keep red on left and green on right. Reverse on the way back in.) Lighthouses have always guided sailors away from rocky points.
Keep a lookout:
- Are you checking your course?
- Are you too close to places you could run aground?
- Can you see indicators that you’re still on the right path?
6. Harness The Elements
One art of sailing is the ability to consistently get the most out of the elements at hand. Experienced sailors are able to read the set of the sail, the pattern of the waves, the way a boat rides in the water and the clouds on the horizon. Adjustments are made on a regular basis on maximize effort.
You can use this principle in evaluating how you spend your time and your return on investment. You want to continually refine what works and abandon what doesn’t.
Maximize your efforts:
- Are you working at peak performance?
- What actions can you refine?
- What do you need to stop doing?
7. Correct Your Course
The entire time we were out on the water, whomever was steering had to keep make small corrections to keep us on course.
Wind, waves, the boat and my steering all combined to cause varying degrees of drift.
Our lives drift off course as well, nudged by pressures of work, family, friends, fitness and more. We need to continually check our momentum against the our goals.
Check your course:
- Do you need to hire or partner with more or new crew members?
- Do you need to adapt your tactics?
- Do you need to change your direction and return to your initial course?
8. Enjoy The Voyage
Throughout my trip, I was continually aware of how much I was enjoying it.
As you move through life, all too often your focus can shift to being ‘happy’ or having ‘fun’ later, when you’ve achieved the measure of success you deem necessary.
Waiting is a surefire way to miss the best parts of your life. Do all you can to appreciate the now and enjoy your journey as well as anticipating the rewards of your hard work.
Consider:
- Are you living your core passions and purpose?
- Are you looking forward to the outcome?
- Are you enjoying the journey?
Use these tips to live out the passion and purpose of your life and sail into the life of your dreams.






