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In The Wake of the Cap'n

Updated: Feb 16, 2021

Photo: Mike D.

They used to call him Cap'n. He was my biological father, but people called him Cap'n. Details beyond that are, shall we say... cloudy. But the weight he straddled me with is one that I had no idea I was carrying. But it has become very clear recently and I am looking forward to releasing that weight to the sea.

So why sailing? People ask me that often these days. They've known me for some time and I never really talked about sailing. So why am I so obsessed with sailing now? It's all I think and talk about. I'm obsessed.

To me, sailing is a metaphor. Accepting that external factors are out of my control but using my skills and abilities to navigate them as effectively as I can with my best self.. found somewhere inside. Challenging myself to have faith in myself, to find peace, find control, and above all realize that I am enough.

What really started my obsession with sailing was Bernard Moitessier's book The Long Way. Then every book I could get my hands on that had to do with journeying on a sailboat. The common thread in all that I was reading was that taking a sailing journey, a real sailing journey, leads one to deep introspection, to face the dark places within and confront them. To come out the other side with enlightenment about myself and my true value. To actually believe that I have value. This hit me like a lightning bolt.

I was born in a storm. My brother, sister, and I were born in Nassau, Bahamas. My parents met there and they were enjoying their time in the Caribbean paradise as two severe alcoholics. The relationship was doomed from the start. He was an abusive drunk and would regularly beat my mother. I never realized my true awareness of this as a child, but recent self-work has made it clear. My fathers message was received loud and clear to that little child.

"You are not worthy of my love or protection."

The pinnacle of that message was received one night when he was beating my mother and spoke very clearly that he was going to kill the children. I remember hiding in the closet under my clothes.

"You are not safe."

My mother remarried, to another abusive man. This time it was not her that was abused, but my brother and I. We were easy targets to vent his rage. He never touched our baby sister but she witnessed it, and that must have been very painful.

"You are not valuable. You are not enough."

The Cap'n still speaks

For many years I prided myself to have lived through such a thing and emerge OK despite it. But now, in my middle age, that fallacy has come crashing down. I did not walk away undamaged. I carry the weight of those men. I hide my authentic self from those around me because I do not believe that who I truly am has value or that how I truly feel has merit. I have been programmed to loathe myself because that is how I was trained, by masters of the art. They are gone now, but they still speak in my ear the lessons they are so good at teaching.

"What you are is not worth loving."

Hope in the Sea

As I read Moitessier, Slocum, Gélinas, Kretschmer, and many others, I heard a common thread. To do a sailing passage provides opportunity to confront oneself. To face demons, to reflect, to think about your purpose. To sail a long passage takes courage, stamina, and self-determination.

I immediately grabbed onto the belief that if I truly want to live a life of purpose and accept who I am, I must attack this challenge. To challenge myself, to train myself, to buy a seaworthy boat, and to set off on a great adventure. To venture to the sea and make a passage, fight through comments from others and myself that it cannot be done. To believe in myself and attack the dream with methodical precision.

The Cap'n whispers "who the hell do you think you are that you think you are worth this.. that you deserve this?"

I tell the Cap'n that is exactly what I intend to find out.

Every step I take closer to the journey, even though I have just begun, is a small battle won. Every achievement in learning to sail, in making acquaintances with like minded people, in immersing myself in an endeavor that is a gift to myself because I believe I am valuable enough to pursue it; every step is a win. Every step is the volume being turned down on the Cap'ns whispers.

I will find myself, I will reassure myself of my value, and I will believe the truth. That I have value. That I am enough.

And the whispers of the Cap'n will trail weakly in his wake, falling deafly to the sea.


- as this journey continues I will share it here on SailJunky. Thanks for all the encouragement I've received.


Mike D. is the founder of Sail Junky Magazine. Striving to find more purpose in life, Mike writes and shares about his journey to rediscover his passion for living a fulfilled life, especially through the medium of sailing.

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