By Kevin

Why? Because we must.

When Jennifer and I met–on our first date, in fact–we took an evening stroll along Chicago’s beautiful Monroe Harbor quay.

We talked and laughed.We got to know each other. And, we both remember me making a boast. “I’ll have a boat out there some day,” I told her, pointing to the colorful, nautical sloops, cutters and ketches that I couldn’t yet identify by name. I was eighteen years old and she, seventeen. And, up to that point, I had only ever spent time in canoes and car ferries.

But, the thought wouldn’t go away. I had contracted a virus. One with a long incubation period. You see, once a dreamer like me gets into his head the idea of voyaging on a small yacht, it becomes a virus. A virus that is impossible to cure and whose symptoms must be managed over a lifetime.

Seventeen years later, after several careers, several houses, and several children had come and gone (well, the children are still with us), we finally had that small sailing yacht on Lake Michigan. We spent weekends daysailing and learning and keeping the kids from falling overboard.

Then, the virus grew stronger and I struggled to counteract its effects. For my 40th birthday, Jennifer graciously offered to send me on a sailing trip by myself–to go and have the adventure of a lifetime. So, I signed up and crewed aboard S/V Tranquilizer, a Bavaria 46, on its May 2010 voyage from Antigua to the Azores. For nineteen days we beat into wind and ten foot North Atlantic waves. The boat and crew made it safely to the Azores, although the diesel engine did not.

In 2011 my partners and I sold the technology business that we had built over the previous 6 years. Jennifer and I had finally made it. We were financially secure. Neither of us would have to work again if we chose.

We took inventory. Of our stuff. Our children. Our marriage. Ourselves. We had the luxury of contemplation and so we contemplated everything. Through this, we began to understand how much our business had drained us. Unfortunately, over the past few years I had put nurturing the business before nurturing my children or my wife. I had made sure our fifty employees seldom worked overtime so they could be home with their families for dinner–while I was at the office eating my dinner.

Though at the time I thought I was a giving father, I began to realize just how much I had not been involved in my family’s lives.


We decided to rectify it. Jennifer found, read, and shared with me, a pivotal book, A Real Lifeby Ferenc Máté.

We read more books. We talked. We asked ourselves, if we had no limitations, if we said To Hell! with our suburban, midwestern social expectations, what would we do differently? How would we choose to live our lives and structure our circumstances?

And, we didn’t really have a definitive answer. Yes, we knew we wanted to change things. We knew exactly what we wanted to change. But, we didn’t know quite what we wanted to change them to.

We decided that we needed to radically alter our environment for a while, to challenge our comfort zones, to break our daily patterns by way of a one year Family Sabbatical. To focus on us. Away from email and twitter. Away from schools and cubicles. Away from dear neighbors, friends and extended family.

Maybe we would rent a small house on a beach in Dominica. Or a small cottage overlooking the ocean in Greece. Or hop island to island on a sailing yacht in the warm waters of the Caribbean.

And the virus, having laid dormant for several years, began to stir. The lifelong dreams of voyaging were too strong, too vivid. The thought of spending our year anywhere other than on a sailing yacht became unfathomable to us.

So, here we are. We are doing exactly that. We are pushing ourselves beyond our comfort zones, homeschooling our kids, spending our time together, in order to better understand ourselves and how we want to live our lives moving forward. On a sailing yacht…

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