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Keeping a Dream Alive May Mean Keeping a Dream to Yourself

We just returned from two weeks of visiting my relatives in Arizona.  We stayed at my fathers home and really had a great visit.  Sometimes family visits can feel like being trapped in prison with no way to get out or around, but we were lucky enough to have a relative lend us a car and my Dad did a great job of filling the calendar with side trips that broke up the visit/eat copious amounts of food and drink beer routine.

The inevitable question was asked.  What are you doing now?  Which was promptly followed by, What are doing next?

As I answered honestly I could see a mask of disapproval drop down or sometimes the interested party would turn off like a television and my response would go in one ear and out the other.  They can’t be blamed really.  When you talk to someone who lives in the desert about sailing it’s like trying to explain calculus to a dog.  They just smile back at you.

With a little more than a month back on land and down to our last dollars, I’ve been trying to work out a strategy that will feed the soul while still feeding the mouths.  When you’ve gotten a taste of the freedom of being on a boat (and a healthy dose of fear as well) it’s hard to let that go with the “9-5, two weeks paid vacation” strategy.  Even worse, the more time you spend on land the more you lose touch with that feeling of freedom and the expansion of time which leads to personal introspection and contentment.

I’ve been reading a book by Andy Deering called, “The Best Life that Money Can’t Buy”, that was actually given to me by a fellow sailor and reader of the blog, and it presents some interesting ideas.  In a nutshell, it talks about how not to get trapped into the 9-5, two weeks paid vacation mentality and live an extraordinary life.  I can’t apply his philosophy directly, but it certainly gave me food for thought.

Be the Main Character in Your Own Life

As I was working through these ideas I would share them with my father and a few relatives.  To my dismay (I don’t know why) the typical response was “get a job” in some more polite form or another.  It’s not like I discussed with my friends and family a plan to buy a new car or take a grand vacation.  I was talking about a lifestyle outside the box, sometimes off the grid, often unconventional, and certainly unpredictable.  What did I expect them to say?

The good news, I’m confident that our path as a family, together, is more important than the security of a paycheck.  My father was beside himself when I told him I’d rather work at McDonald’s than take a job which required 75% travel and be away from my family.  I believe my responsibility as a father and parent cover more than providing financial security.  I want my children to be confident, capable, and self motivated- which requires the support and presence of both parents.  

The bad news, don’t count on the support or even understanding of your friends or family when discussing a life that is so foreign to them that it borders on lunacy.  In their efforts in trying to protect, the offer and may even implore a conventional wisdom.

Conventional Actions derives Conventional Results.  Extraordinary Actions derives Extraordinary Results.

How to overcome this?  Baby steps, my friend.  Baby steps.

We started by telling friends and family we were just taking some time off while our house was rented to go sailing.  We didn’t even really tell our neighbors the true nature of our plans.  Halfway through our trip we alluded to just dropping in for a month to maintain the house before continuing north on the boat.  Then we started to ‘justifying’ living on the boat as an economical alternative while the home on St. Simon’s was rented.  That morphed into ‘living on a boat at a marina full time’, which has turned into ‘living on a boat in a marina until the baby is born’.  Now we’re starting to talk about working seasonally and cruising on a boat.

The baby steps also allow you to try your unorthodox plans without fear of commitment and see where it takes you.  While there are a lot of people that live on their boats and a lot of people that have sailed around the world- they certainly are not the majority and you might not have the advantage to have one as your mentor to give you trusted advice and encouragement.  I know I don’t.  We ‘think’ we like something, try it, adapt to reality, and decide for ourselves the next course of action.  This way I don’t feel like a failure for making some big extravagant declaration, “We’re going to sail around the world!”, and then fail to leave the dock.

Live an Extraordinary Life.

If you have a dream, break your friends and family in slowly.  Let them digest your wild and crazy unorthodox proposal gradually before revealing the true nature of your plans.  Remember, conventional wisdom works for most people- but who wants to be conventional?

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2 comments to Keeping a Dream Alive May Mean Keeping a Dream to Yourself

  • Ceal Potts

    Architect turned real estate developer turned sailor and now the writer of a surprisingly enjoyable blog. I was searching for a CSY on and that’s how I found your Web site and excellent blog. Oddly, we live on another coast and sit in our living room at night and probably once a week take a look at your blog. We actually really like your boat, a lot, but right now it’s located on the wrong coast. Doh! Having just been in Arizona and hanging out with family I know how difficult it is to break the desert dwellers in and hearing the response: “You want to do WHAT?” You have a beautiful boat and family. Keep up the great work and thought-provoking posts.

  • big cheese


    I was born in the desert, but all things meaningful to me are around water. Go figure?

    It’s hard to explain to others how time stretches out when I’m on a boat and suddenly life becomes very linear, orderly, even precious. It’s hard to define value, but that’s it for me. There’s no clear roadmap to happiness. Success is easier to replicate, but not happiness.

    In whatever form that takes, however it may happen- I wish you that. Happiness.

    I am blessed with a beautiful, courageous wife and doubly blessed with a beautiful baby girl.

    Thanks for the comments!