Living The Dream

Teresa Carey Words 17 Comments

I am encouraged by all the posts, emails, and messages that I get from people who are inspired by what I am doing. “You’re living the dream,” they say. Yes, people romanticize it. “Oh, you live on a boat, how wonderful! To feel the wind in your hair and nothing but openness ahead” they say…”I could never do that!” But of course they could. Taking each challenge one day at a time.

I think I romanticized living on a boat too…perhaps too much. Sailors are romantics and romantics are fools, so I must be a fool. But the dreamer in me keeps on making somewhat rash decisions like this. It has been a part of my life journey all along.

After my second year of college I spend the summer in Chicago. On this day it was truly the “windy city” and I spent the afternoon sailing with a friend. “Whooooeeeee!” We would yell as the wind howled across our ears. I was hiked out on a trapeze, dinghy sailing. I felt like I was flying over the water. We yelled to each other over the screaming wind. “I’m moving to someplace where there is wind like this all the time,” my friend yelled. “Me too,” I replied. “I’m moving to Brazil.” “Me too!” And so, the next day I found myself at the Brazilian consulate trying to figure out how to move to Brazil.

I decided not to go to Brazil. I wasn’t looking for that experience, but instead for one that would set me free, like sailing. I did, however, decide not to return to college. My parents warned me that it was a bad decision. “If you don’t go back now,” my father said, “you probably will never go back.” But I had to take the chance. So, I did.

That year was followed by many years of quick decisions full of passion: I followed a BS in Environmental Science with a MA in Theater, convincing myself and Ohio University that I belonged in theater school. I spend several months hiking and rock climbing, while living out of a backpack and sleeping on the ground. I flew to the west coast to sail on a schooner and “jumped ship” after only a week. I hitch-hiked up the east coast. I moved and moved and moved again, living in strangers’ homes, a fraternity house, a base camp, tents, and even my car. All the wile pursuing whatever my interest and spirit dictated. And it has been good…mostly. But, when life is mostly good, then I must be doing something right. 

Buying a sailboat was another quick decision accompanied with warnings from my father, “Wait until you are more settled,” he said. And I wondered how one who is “settled” would ever want to cut lines and set sail. By then I would be saying, “oh I’m too old to sail. I’ll have to wait until the kids are out of college.” But, taking the warning I processed the pros and cons of the decision. And I thought to myself, “What is the worst thing that could possibly happen from this decision.” The answer was clear; I could struggle financially, blow through my savings, and eventually have to sell my boat. Now, nearly there, I wonder if I will regret it all.

But back to my original thought…about “living the dream.” I would hate to disappoint any of my readers, but I am not sure if I am living it. It is not my dream to be living in such a small space, tied to a dock, and working only temporary jobs that lack room for enough of my own creativity. But maybe I am one step closer. Besides, experiences like this continue to color my story. I believe that eventually it will turn around. I’ll find work that I like (hopefully a full-time teaching job again) in a place where I can liveaboard and save money for the time when I can truly set sail and discover more of that dream.  

Comments 17

  1. Steve D

    I think most people who live on their boats will not say it is an easy way to live. Living simplistically does not equate to living easy. In some ways it might be cheaper, but living on a boat is not one of them. Hopefully you are not getting to discouraged. Winters are rough, but the rest of the time, being aboard is wonderful.

    Hang in there. It is a very different way to live. It will take a bit to get used to it, but in my humble opinion, it is still a great way to live and enjoy what life has to offer.

  2. Stuart

    That last paragraph sums it up pretty well. Just living on a boat doesn’t give the lifestyle that most people associate with it. A boat is a small space which I think is why the uninitiated look for such big boats. The life that people do tend to associate with living on boats is about the experiences that come from moving from place to place and seeing and doing new things, which is why a smaller boat works for people, when they do actually set off. It is not easy to just hop on a boat and venture out, because we do need to replenish our resources as we go.
    Provided you keep your main goal in mind, there is no reason that you can’t use this time to get yourself in a position to venture forth. Just remember where you want to go and direct your resources in that direction and don’t lose sight, sending your resources into just maintaining where you are at now.

  3. matthew

    Winters aboard are difficult.
    The “living the dream” aspect seems very far away. The only benefit is the challenge itself. Like a lot of dreams, there is a flip side that you are experiencing right now. Also, if you are tied to a job that you don’t like, it clouds everything else.
    Think of it this way: if given the choice, would you prefer your current living situation if you had a job that you liked? Or would you exchange it for a comfortable apartment and a job that you hated?
    I know what my answer is!

  4. Post

    Hmmm….good question, Matthew. I would, without a doubt, choose my current living situation with the job I love. So I’m starting to apply for future jobs. I’m not one to need a comfortable apartment…I think its more about meaningful, pleasant work…and sailing!!!!

  5. Naomi

    Funny how the grass is always greener … I’m living in an apartment and going to the same place to work every day. It’s the longest I’ve stayed in one place, and living on a sailboat, even one that’s moored, sounds a lot more romantic than sitting in traffic every day.

    It does sound tough, but it also seems like this will be a memorable part of your life.

    (and from one theater major to another, I’d say you’re doing pretty well)

  6. Nick

    Hey Teresa,

    Ha, living the dream! There is nothing very dream-like about being in a cramped, damp space tied to the dock… Whenever anyone says I’m living the dream, I happily offer them my boat and explain the situation. Soon after they change their minds!

    However, my suggestion would be to make a plan. You have the boat, you’re 80% there. I don’t know if you’re in debt to own it, however if you own her (or is it a he?) outright, you’re in good standing. It is very demoralising living on a boat and just working a normal life – The romance is completely killed…

    As it’s winter, I’d make a plan to leave in May, and stick to it no matter what. Do not worry so much about the money – Get whatever you have and don’t be brash with it. Socialise with other sailors and lot, and let them know you’re situation – A young lone sailor (especially a female) is looked upon favourably by the majority in a sport dominated by people much older. Oh, and read lots of foolish romantic sailing literature through the cold!

    Anyway, hang in there and do a big voyage. If you don’t like it, sellup and move on – It’s definitely not easy, and not for everyone!

    Good luck, fair winds, dry cabins & quiet halyards,


  7. Pat

    Hi Teresa
    Hope your dream comes to fruition. As a keen (but nervous) sailor I get to sail pretty regularly on the beautiful bays of Southern Tasmania (Australia). I own a Columbia 27 and race with a crew of all women on our Twilight races from January to March. I sail almost every week with someone or other. It is a great sport and we girls have done well in keeping up with the men. Can I link to your blog from mine? See my web address.
    Good luck

  8. Wilson

    Twenty years from now you will be more disappointed by the things that you didn’t do than by the ones you did do. So throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover.

  9. Chris


    I admire what you are doing. I wish I could do it. I am not really into the voluntary simplicity movement, but I wanted to pass on a couple of resources that have helped me. Like you I have felt for a long time that unnecessary possessions are a burden.

    Some resources that have helped me understand money and my relationship to it are:
    •The book, Your Money or Your Life: Transforming Your Relationship With Money and Achieving Financial Independence by Vicki Robin and Joe Dominquez.

    Fulfilling your dream is going to take money and this book (and associated websites) can help you understand how you can become financially independent so you will not require a job for financial resources. I don’t want to write a book review here so if you want to know more, please feel free to email me.

    I wish you success in your endeavors.

  10. Mom

    “I think I romanticized living on a boat too…perhaps too much. Sailors are romantics and romantics are fools, so I must be a fool.”

    YOu have never been a fool…like we told you since you were just a wee little thing… have so much to offer..and so many things to conquer…….nothing wrong with being a romantic, just learning how to weave it all into reality….you are paving your way, and I have never had any doubts you will find what it is that is most rewarding for you….and to learn that it is ok to accept certain things into ones life is not necessarily compromising ones true beliefs and wishes… I love you P.S. Perhaps Dad’s dreaming “helped” develop that romantic viewpoint…he too is one

  11. Stanley

    Congratulations on your dream. To say “don’t give up” does not apply.

    No matter what you do in and with your life your spirit will show through. You are one of the fortuate that live from within.

    I am in my 60’s now, been a pilot of small aircraft since highschool. Flew helicopters in Vietnam, ridden motorcylces throughout NA, and been messing around in boats. Got a Nor Sea 27 now and am planning on “The Big” sail one day. Have been on the hard after the last hurricane, will have the projects done soon after Christmas.

    The New year will find us sailing the barrier islands East toward FL in the firstleg of the “big” trip.

    Sail on sailor

    Cpt. Gypsy
    Cpt. Jasmine
    SV Gypsy Moon

  12. bill w

    Living on your boat at this stage is essential. You will learn what you really need for cruising and most importantly how and where to store it. Too many cruisers overburden both their boats and themselves with stuff they think they might need only to discover down the road that they are dragging their old shore life along with them. Self reliance is the key to successful cruising. Learn your boat inside and out and how to fix it. Every challenge overcome builds your confidence.Never be afraid to ask questions but as Reagan said “trust but verify” Good luck and God speed.

  13. Hector

    Well I just stumbled onto your site and am quite inspired. I am on the docks looking out. My last child is a senior and I am ready to buy and start the process. Any recommedations?

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  15. Liz

    Since my daughter got the boat bug I’ve been trawling the sites.She’s got as far as living on board in Los Angeles, with her dog. More worries for me as she says the area round the marina ie docks is notoriously dangerous. At least she’s warm.
    Yours is a lovely site, hope you are tough! Good Luck.Liz (a former teacher too)

  16. Douglas

    Ahoy Teresa, We wish you the best ,,,, this is my wife’s website, and you can use it if , you can !

    You have much courage, from what we read,,, we wish you a short Winter, and an early Spring,,,,

    Sincerely ,,, Douglas

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