Anywhere: Living on a Sailboat

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Anywhere: Living on a Sailboat

I suppose the simple answer to the question is simplification. But, then, that’s a bit oversimplified. Maybe distillation is a better word. “Why do you live on a sailboat?”

“Lots of reasons.”

For many years, Jodi and I would pack up the kids and head to Destin, FL for our summer vacation. It’s called the Emerald Coast for a reason and it does not disappoint. Destin was everything that one could want in a tropical island beach without actually having to pay to visit one. After each visit we would look at homes in the area and I would look for jobs. We never found the right combination. I kept the thought alive, always looking, searching, thinking.



I have always been enamored with the romantic idea of living next to the water; beautiful, clear, blue water.

After 19 years at the same company, I realized that my “career” goals would never be fulfilled there. My objectives and the company’s plans diverged. I was looking for some type of ownership opportunity and that was not to be afforded. I jumped ship and started a business. It wasn’t to become a millionaire. And I certainly did not want lots of employees and all the complications that entails. I simply desired to choose my own direction.

I was looking for freedom and a bit of financial security.

Through our business, Jodi and I were grossing more than twice as much as I was making at my previous job, but we weren’t moving forward financially. We hadn’t changed our lifestyle at all. But, we had substantially higher tax bills and more expenses related to the business. And we couldn’t control most of those. We were always at the mercy of someone else. So much for freedom and financial security.

I decided that there had to be a better way.

I discovered that I had considered my life as a means to an end; just a way to achieve a goal: financial security and a “happy” retirement. What I really needed to do was look at my life, the whole of it, as the goal itself.


I began thinking about all the constraints that we had on our lives: mortgage, client demands, rent for the business, car payments, credit cards, insurance requirements, student loans, medical bills, a fixed address, laws, taxes, etc. It was, literally, The American Dream. I felt like it was some sort of cursed alternate reality. I talked to Jodi about it incessantly.

The Internet is a wonderful thing. It allows for the free flow of information instantly. What I found on it was that there were lots of people that were living life on their own terms. Sure, there will always be constraints. That’s what society implies, but, as individuals, we have some ability to choose which constraints we will subject ourselves.

I was sure my life was not what life was supposed to be.

I really didn’t know what I was looking for, but I came across several blogs where people had ditched it all, bought a sailboat and just sailed around. Families, couples, couples that started families while sailing, individuals. And the places that they visited − places that I could only dream about. Or maybe . . .

I slowly introduced Jodi to the idea. She’s always receptive to an idea if she believes it will go nowhere. “That sounds great!”

The more I read, the clearer the realization became that I could change my situation, my life − our lives. Minimalism, simplification, downsizing, all things that appealed to me, seemed to be gaining favor. There were plenty of people blazing trails for me. I simply had to choose which one to go down.

I made a short list of what I was looking for:

  • close to the water
  • freedom to travel
  • simple
  • inexpensive

A sailboat filled all the requirements.

By selling everything we owned, paying off all our debt, we could focus on being alive instead of merely making a living.

And so we did.


Living on a Sailboat

I discovered that I had considered my life as a means to an end; just a way to achieve a goal: financial security and a “happy” retirement. What I really needed to do was look at my life, the whole of it, as the goal itself. All that other stuff was just incidental to the journey and most of it was preventing me from experiencing it.

That thing that most of us crave, security, is something that really does not exist. That’s not a pessimistic statement. To the contrary, it can be seen as optimistic. It means that there is adventure, wonder and beauty to be found.

We decided to use a sailboat to go find them.

Also check out Growing Up in Cleveland.


Clint Williams

Clint Williams

Clint is just an average person that throughout his life has yearned for peace and simplicity. He is a freelance writer, photographer, and thinker. He currently lives aboard a sailboat with his high school sweetheart and wife where he is close to the ocean. He plans to travel the seas in search of uncommon and wonderful places and experiences.