The Triton


Ask tough questions to get answers for progress


Sometimes it can be helpful and enlightening to take some time and do an honest self-assessment. You know, take stock and take a good look at where we are, who we are and where we would like to go. These exercises of reflection and raw honesty can lead to small positive steps or be truly powerful life-changing moments.

As a life coach, I have conversations quite often with people who are considering change, thinking about their path and desiring more clarity and purpose. I have spoken to a number of folks in the yacht chartering world who are wondering if it’s what they want to do long term and are thinking about another possible lifestyle.

This is when it’s helpful to check in with ourselves, but we must check in openly and honestly. We can’t ignore some hard truths and even painful lessons in our stories.

There is no set time frame for doing this. You could try scheduling it in but it’s driven more by events, experiences and feelings. I have had a number of, let’s say, minor assessments that led to some course corrections, but there were also two major life changers as well.

Now it just so happens that these major assessments took place around what could be considered by some as significant age numbers. The numbers may have played a role but what was going on and what I was feeling led me to major assessments at around age 30 and age 50. This leads me to believe that at 70, something will be going down. I can’t imagine what that might be but I like the idea of it.

So my big assessments came at a time that I’m sure most psychologists would not find surprising, but this can take place at any age and place in our lives.

This exercise of assessment reminds me of the age-old wisdom in the statement “know thyself.” To truly know oneself, you have to check in and reconnect to the true self we can easily get detached from. This is where we must take care not to believe the story the ego will try to sell you.

Be careful with that one. This is the real, honest look at things that includes victories and achievements but also disappointments and regret. It is not a time to beat yourself up about anything, but rather to accept, admit and understand. That is the way forward. That is the path to your growth and continued development.

So what is involved in this assessment? Basically, we want to ask ourselves some questions and try to answer them. The answers don’t necessarily come immediately, but if you go fully into this, the insights will come.

The big question I often remind coaching clients of is “what do I want?” If the answer isn’t clear, keep asking questions.

If it’s a career change you’re considering, you may want to ask yourself; what am I good at? What comes naturally to me? What could I help others with? What do I need to work on? In what area do I need to improve the most? There are many questions to look at indeed.

Some of the answers may bother you or make you a little uncomfortable. That’s OK. That just shows you’re asking yourself some powerful questions. Remember, you are trying to get to an honest understanding with yourself to pave the way forward. It isn’t always easy, but I can tell you from experience that it is worth the effort.

When I begin working with a new coaching client, one of the first things I ask him/her to do is to write me a biography, a condensed life story with the highlights, meaningful events and experiences, but also with the lowlights and disappointments. It’s challenging for some but they usually feel good after doing it, and it’s another form of assessment.

As coach, I get a better feel for them, a clearer picture of where they’re coming from. The client completes a reflective exercise that can open their eyes about where they are so we can start there. I’m a big fan of writing things down, writing things out.

If you are in the yachting profession or really any career and find yourself in that should-I-stay-or-should-I-go place, sit yourself down and start asking the good questions. Be honest and I promise you the answers will come.

Rob Gannon is a 25-year licensed captain and certified life and wellness coach ( Comments on this column are welcome at

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