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I just turned 54. I am slowly rebuilding a sailboat. I intend to take it on a once-in-a-lifetime journey before I am too old. I am, apparently, a cliché. An upper middle aged guy, mid-lifing, a little bit lost.. blah blah blah.

So what is the cliché. Guy has idyllic dream of owning a sailboat. He buys an old cheap boat with big plans to sail to far off destinations. He spends vast time & resources buying the boat and getting it ready. Reality slowly starts to leak into the dream. Costs of parts, slip fees, ripping out a 50 year old toilet, finding rot in very hard to reach places, on, and on, and on..

If he is lucky enough to get the boat in shape to make his journey then, once shoved off, the reality of what that is really like will set in. Sleep deprivation, wet, cold, seasick, bored, storms, becalmed, mechanical issues.. The idyllic dream is never the reality.

I’ve heard various people joke about the broken dream boats for sale in Panama, Hawaii, etc. People that start their dream only to say f%@k this.. sell it.. I’m out.

The dream ends and he is the cliché, the butt of the joke.

I’ve been working on this boat for three and a half years now. It’s been slow but I am making progress but more importantly, I am staying committed. The reason I started the whole thing was because of the very idea that out there, on the ocean, I will face the challenges mentioned, but more importantly I will face myself. I will be alone with my thoughts. I will not be able to hide from them. I need to go into my mental woodshed with my demons and only one of us will prevail. I need to find my way back.. I am lost and I will not accept it any longer.

I recently listened to Jerome Rand speak on his podcast ‘Sailing Into Oblivion’ about Mental Health while Solo Sailing. (Episode #176) Jerome provides some seriously good insight, and he should know. He’s been around the world via the Southern ocean non-stop and single-handed. In the podcast he discusses different aspects of the topic, as well as a story in Outside Magazine titled ‘My Father’s SOS - From the Middle of the Sea’. It chronicles retired psychologist Richard Carr and his ill-fated journey crossing the Pacific ocean. It’s a great article and you can read it for the details but suffice it to say that Richard lost it at sea.. in a big way.. and he didn’t return. Richard didn’t emerge from his woodshed.

Perhaps my challenge to confront myself at sea is precisely why I shouldn’t go there. Maybe it’s too dangerous. Maybe, like Richard, I will not emerge victorious. But I don’t want to entertain that risk. My journey of self discovery needs to happen.. I am well aware I have the demons.. I need to leave them in my wake if possible. It will likely get ugly, and I have been trying to prepare for that in various ways.

It’s not a cliché. I am not imagining Margaritas in the cockpit or calm Caribbean anchorages. I do not see only sunny fair wind days. I am preparing my spaceship for turbulent mental & physical exploration.

The time we spend on this planet.. it has to be worth it. I heard an interview on the “On The Wind” podcast with adventurer Andrew Bedwell where he mentioned that on our headstones there are dates for when we are born and when we die.. and in between is a dash. Our dash wants to be the most fulfilled, impactful dash possible.. and I agree.

Why are we here if not to challenge ourselves to experience life to the fullest and to stare down adversity and challenges like a scrappy street kid does to the school-yard bully.

It's all hard.. this sailing adventure.. refitting a sailboat that is almost as old as I am. Dealing with all the hassles that come with boat ownership.. all of it. It is all very chaotic trying to prepare for this exploration while holding down a seriously demanding job, raising two kids.. all of it..

But a cliché? No. Fuck That. The remaining part of my dash will not contain mediocrity or accept apathetic bullshit. I am challenging myself to live and that is what I'm going to do.


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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