"Shit just got real"

I seem to be having a serious case of deja vu... Repeatedly.  For months now, time and time again I have stopped in my tracks, frozen.  For that moment, I have stood there in sheer terror quietly thinking to myself - "Shit just got real".

I always thought that when the time finally came for us to make our move to the Caribbean, it would be so easy.  Because I have such malice for Connecticut, I thought that when the time came there would literally be smoke rolling off my tires and this state that I have detested for ten years would be nothing more than a fading landscape in my rear-view mirror.  Wow, was I ever wrong.  No surprise there really, I tend to be very talented at being wrong.

The truth of the matter is that making the decision to pursue our dreams was and is terrifying.  We are leaving a known with financial security to venture into something entirely new with an uncertain outcome.  We are leaving careers that we have built and maintained to try something new that we might not be successful at.  Maybe I just don't have the balls, but for me it was far harder than I ever imagined.  I have to keep reminding myself that we are also leaving a place that was literally killing us.  We are leaving a place where although we had good careers and income, we lacked anything vaguely resembling a life.  I have to keep remembering we are getting the chance of a lifetime to follow our dreams and create a new life.

After weighing all the pros and cons, eventually a hard decision has to be made which can not be reversed.  It's a lot like jumping into the deep end of a cold pool.  You want to swim, you know you can swim, but that water is cold.  You just left the diving board and there is literally no turning back.  That's where we are right now - in limbo.  We are far from the diving board, hanging in mid-air.  We have been looking forward to the swim ahead for a long time, but we are terrified of hitting that cold water for the first time.  The unknown is unnerving.  "Shit just got real".

When I met with my boss, whom I have known and highly respected for ten years now, and explained what we intended to with a resignation, "Shit just got real".  When we rented a UHaul trailer and pulled a load of "stuff" to our summer house, "Shit just got real".  The day we officially closed on, and became owners of a 50 foot yacht, "Shit just got real".  Our house was listed on the market, and a few showings later we were signing offers and contracts, "Shit just got real".

And now, as I sit here writing this, I'm surrounded by boxes marked "Ship to boat", "Summer house", etc.  We have spent our weekend sorting through all our life possessions, and preparing for an estate sale of the remaining contents of our house, furniture, etc.  "Shit just got real".  This is really happening.  We are hanging in the air off of the diving board, with an inevitable big splash coming our way.  Thank goodness the water in the Caribbean is warm.

Step 7: Throw out all the steps - It happened

Taken in April, contemplating how I would eventually make my escape

I have said many times on this blog, the difference between a dream and reality is "simply" putting a plan in place and working towards it.  I have also said many times here, that while I had a plan, it was missing a lot of pieces.  My whole thought since I stood on the bow of a boat in the Caribbean and said "I'm going to do this", was to attack the pieces of the plan that I could do here and now.  I figured that if I worked on all the things within reach now, that eventually somehow the other missing pieces would eventually come to me.

It happened.

No seriously - It happened.  A seemingly single event, set off a chain reaction that could not, and would not be stopped.  I had optimistically pictured my plans coming to fruition (somehow) in a five to ten year time frame.  Forget that.  This is happening now.

Taxes.  That's what it was.  Taxes.  In 2014, I got literally clobbered with taxes.  That simple fact started a thought process and a conversation with a friend who is a charter boat captain.  That conversation grew during a trip to our beloved St. John, where our friend came to meet us for dinner.  That dinner conversation grew into bigger plans.  Those bigger plans turned into a random phone call with yet another captain.  That random phone call turned into that captain reading our story on this blog.  The reading of our story here turned into a flurry of phone meetings and another trip down to the islands.  That trip down to the islands turned into an amazing opportunity, with some great people betting on a couple young and hungry dreamers.  Those great people betting on a couple hungry dreamers, turned into a complete plan - my plan with all the missing pieces finally filled in.

That amazing chain reaction of events couldn't be stopped.  It wouldn't be stopped.

Over the past years I have struggled with my state of existence.  I'm not "living" here, I simply exist.  I get to live only during short periods of vacation and weekends that I can escape Connecticut.  Existing here is nothing more than being in a rat race of continuous bumper to bumper traffic, inching ahead - there's simply not enough time for anything else.  Sure, I have a great job and that certainly has allowed for a lot of things, but I'm not living.  I'm not experiencing life.

At the same time, 2014 has taken so many loved ones away, far before their time.  I watched a great friend take his last breath.  I'm not sure I'll ever be the same after that.  I came to the hard realization that life is short, and I'm not living.  It happened - all the pieces of a real plan to start anew were presented before me, and I'm not letting it pass.

It happened - We're making our great island escape aboard a 50 foot yacht.

Step 2: Choosing a sailing school

"Island Dreamer", a 41 foot Morgan Out Island, our platform for ASA 103, 104 certifications

"Kermit", a 20 foot Balboa we used for ASA 101 certification

When Sharon and became serious about learning to sail - for us formal education was the only option.  I personally don't know anyone locally that sails, and I also wanted a skilled instructor that would adhere to some sort of structured program, versus some guy saying "pull that line over there and crank this thing-a-ma-jiggy" in between chugs of beer.  I do know one captain that is not officially an instructor, but someone whom I would fully trust to teach me.  However, his west coast location, and the fact that we would have no official proof of my instruction, eliminated him as a possibility.  When considering a life aboard, I wanted to know we had educated ourselves correctly, and not cut any corners.  After all, one day our lives might depend on it.

Sharon reviewing ASA course books aboard "Island Dreamer"

After doing much research, I also decided that we should obtain some sort of standardized certification.  While no specific license is required to sail (non-commercially), US Sailing and American Sailing Association are two widely known and accepted standards.  By showing these levels of certification, it is official proof of the training one has accomplished for their sailing resume - be it for bareboat chartering (renting and skippering a yacht yourself), or for possible employment.  Deciding that education standards were a must helped to narrow down the type of schools we would consider.

Tim at the helm of "Island Dreamer" under Capt. Margie's command

The American Sailing Association and US Sailing both have similar levels of certification, starting with the basics of keelboat sailing, progressing up to and beyond bareboat chartering.  My goal was to achieve proficiency to a level in which we would feel comfortable enough in our skills to safely live aboard a 40-50 foot sailing vessel.  With this goal in mind, it was decided that we should aim for Basic Keelboat, Basic Coastal Cruising, and Bareboat Charter certifications.

Sailing "Island Dreamer" through a narrow mangrove channel

Google search quickly found a local school on the Connecticut's southwest coastline of Long Island Sound, offering US Sailing courses.  On one hand, the benefit of a local school would be the ability to schedule at least a portion of the schooling on weekends, thus saving vacation time.  On the other hand, a local school is also a downfall.  We don't like Connecticut, nor do we feel we fit in here - so why would we ever feel comfortable with a Connecticut school or a class setting here?  Also, education of any flavor is generally expensive, and this school was no exception.  The final nail in the coffin for the local school, was the complete unresponsiveness from the owner when I asked for additional information.  His nonchalant and seemingly non-caring attitude towards me as a possible client quickly helped me eliminate his school as an adequate solution.

Sharon at the helm of "Island Dreamer"

The next best option to local training, was to find a school somewhere in an enjoyable area, where we could pursue our education as somewhat of a working vacation.  I found lots of options in the Virgin Islands, as well as Florida.  But one school really stood out.  Touting the advantages of private, "couples to couples" instruction (a husband/wife instructor couple teaching a husband/wife student couple), as well as a no-yelling policy, Island Dreamer Sailing School grabbed my attention.  Located in Miami, and offering certification while sailing in the Florida Keys was also a very appealing benefit.  While Sharon was still unsure, I was quickly beginning to think this was the right school for us.  Even with the added cost of airfare, this school was still less expensive than the local option we had explored, and offered a much more private and tailored program considering there would be no other students.

I placed a call to Harold Ochstein, the owner of the school, and also an instructor.  Harold immediately convinced me that he truly understood our needs, and our reasons for seeking knowledge towards a new life adventure.  This was not a used car salesman making a sale, this was a guy that had been in my position, and had gone through the things we were facing.  Cementing our choice, Sharon also placed a call to Harold herself.  Harold's calm, reassuring nature soon put all of her concerns at ease.  With our decision made, and acknowledgement of the work ahead of us, dates were decided and contracts were signed.

Capt. Harold Ochstein grilling a great meal aboard "Island Dreamer"

It was real now.  Funds were committed.  Much like college, once a few thousand dollars vacates your checking account, it all gets a little more serious.  An even more valuable commodity, vacation time, was also entered in work calendars.  More precious than gold to us, we would have one full week less to spend at our vacation home to ease the stresses of living in Connecticut.

Promptly after booking with Island Dreamer Sailing School, our course materials arrived in the mail.  With a matter of months until our week aboard Island Dreamer with Captains Harold and Margie, we had three course books and a lot of material to cover.  Each of the three levels of certification we were pursuing would require passing a written test, and also demonstrating our skills via a practical assessment aboard.  It was immediately apparent that if we were to be successful, we would need to cover all the course materials before our week of training aboard Island Dreamer, thus allowing us to focus fully on all the physical sailing skills.  Our lunch hours and evenings would be filled with regular reading and study sessions.  Our week aboard was approaching.

ASA Course Materials

Step 1: Inception of a plan

Magewind moored in the Bight,
Norman Island BVI

A desired goal is nothing without a plan for execution.  Think about it.  Let's say you want to build your dream home.  Hammer, nails, saws, and wood don't simply start flying around in a flurry of construction.  Your home starts on the desk of an architect, who carefully and painstakingly devises drawings and specifications for your future personal castle.  Likewise, even the most ingenious plans lay completely useless unless a home owner puts them into play by supplying monetary resources and a crew to handle the labor.

And plans, life plans or plans to build a home, are not one dimensional.  They are complex, with lots of moving parts all needing to merge together towards the common goal in harmony.  Seldom does a plan go executed smoothly, nor is it common for a plan to flow in a linear fashion.  As the pieces come together, there are hangups and setbacks.  Research and dedication of resources are committed in iterations until all pieces of the plan have been managed and massaged into that one uniform end goal.  If executed correctly and successfully to completion, the final product of all the hard is a close version of the original proposition.

Currently, we are slightly past the inception of a plan.  We drew a line in the sand and started formulating a loose approach for a new life, a new chapter.  This first important step of declaring a plan and starting to determine the required pieces usually requires some sort of stimuli.  At some moment in time, something is required to set a new direction in motion.  For us, there were a few things.  We have always had the desire to make some sort of life in the Caribbean - eventually.  We initially pictured this as a plan for retirement.  As we traveled more and sailed more, a life on the water began to attract our interest.  Add in the stress and lack of life quality in Connecticut, and our thoughts of a move at retirement started getting pushed forward to an escape from misery.

Steven Ulrich and Debora Ruffe

Next, a plan needs a catalyst - something to spur an idea to life.  Enter Steven Ulrich and Debora Ruffe, owners and operators of "Magewind", a 46 foot catamaran sailing yacht which Sharon and I chartered last fall in the Virgin Islands.  If there ever was a catalyst for change, this was it.  Steven and Debora are charming and doting, and shower their guests with a luxury vacation for which life lasting memories are surely to be created.  Well worth the price of admission to say the least.  But above and beyond being amazing charter hosts, they exude energy and inspire positive thought.  During our time aboard sharing fabulous food, cocktails, and stories, Steven and Debora offered a new point of view and encouraged us to question ourselves and our situation.  While we had been meandering in a Caribbean direction for a few years, this was the spark that ignited a fire and made us look at our loosely gathered ideas as more of a plan, and less of a dream.

Group shot aboard Magewind before saying goodbye

Although at the time we didn't have all the pieces to a plan (and we still don't), it was clear that if we couldn't confidently sail, then there was no future in the plan at all.  Obviously, this is the first and foremost step we needed to take.  If we were going to be serious, it would be required that we commit some time and resources towards exploring our new found direction.  At first it was decided that I would learn to sail.  Quickly I realized this was a half-baked solution.  To be realistic we're talking about living aboard a 20-30,000 pound sailing vessel, on the ocean.  We're not talking about ski boats and lakes here.  The only probable solution was for us both to learn, and both gain confidence in our ability to live at sea.  Operating a boat of this magnitude is mostly a team effort, and add to that the possibility of one of us getting hurt at sea...  Both of us would surely need to get trained.

So this is where we would start.  Our little exploration into our possible future would require quite a bit of work in studying, a week's worth of vacation time for the actual school, and some monetary resources to pay for it all.  Worst case, we might fail in which case we would incur the loss of committed resources.  Second worst case, maybe after going to school we might decide we didn't want to live aboard.  All in all, not bad really - we would still learn to sail yachts which could be used for future sailing charter vacations.

The beginnings of a plan had hatched...

The Flat Tire

I've come to the conclusion that I don't like who I am anymore. Maybe that's too harsh a conclusion. Maybe it's more appropriate to say I don't like what I have become. I came to this realization about a week ago. I was engrossed in the misery of a typical two hour commute home from work in Connecticut, when I came across a car on the shoulder of I-95 north. It was about 85 degrees and humid. There on the side of the road was a sedan with a flat tire. The owner was digging in the trunk for tools. It was painfully obvious he was unfamiliar with the process of changing the tire for which he was about to attempt. Numbly, I drove by.

I drove by.  Traffic was moving less than 5 miles per hour, and as usual, was backed up for over 20 miles. I had all the time in the world to pull over, and I drove by. About fifteen minutes and maybe a mile down the road, I realized what I had done. I could have pulled over, changed this guy's tire for him, and both of us would have been on our way. Instead I drove by. And so did the thousands of other numb, self-important commuters sharing three lanes of I-95 misery with me. We all did it.  We all left this guy and his flat tire, there on the side of the road to struggle on his own. Pathetic. I was thoroughly disgusted for what I had done.

Ten years ago, before I had ever stepped foot in Connecticut, this would have never happened. In the country, we help each other out. This is how we are raised. This is what we come to know as normal. It's a community in which common decency towards others and a willingness to help is indoctrinated. I'm ashamed for what I have allowed this toxic environment to do to me - for what I have become.

In the boating world, it's a well known fact that boaters help boaters. If a boat is in jeopardy, if it's crew needs assistance, another boater will come to aid. It's a cardinal rule at sea that if you are able to lend assistance to another boater in distress, it is your moral duty to do so. Every book I have ever read about cruising life and living aboard has always mentioned the help one can find in other boaters within an anchorage. Authors encourage their readers to proceed into the unknown, to find calm in knowing there are plenty of other boaters ready to lend a hand.

 It's this sense of community and civility that is missing from urban environments. It's this common respect and consideration for fellow man that is eroding from society, and is seemingly extinct from urban living. While I fear failing at making a new life aboard my boat in the islands, I welcome finding a sense of community and simple common consideration which is lacking in my current situation.

So if I ever spot you on the horizon off my bow struggling with a "flat tire", no worries - I'll gladly do what I can.