How We Bought a Sailboat and Sailed Away

The Lifestyle

I live on a sailboat. A 44′ sailing catamaran. We travel from island to island in the Caribbean. Our crew includes my husband, myself, and our two young children.

This lifestyle is drastically different from our previous one. Before we chose to sail away, I worked as a full-time accounting professional in the healthcare industry. My job titles over the past six years have ranged from Financial Analyst to Chief Financial Officer (more on that in a bit).

I went from having a negative net worth to being able to afford to sail away from it all on a mini retirement that could last anywhere from six months to three years.

Our 44′ Knysna bluewater catamaran docked in Grenada

Quality Time With Kids

The problem was that I worked too much, and I always came home tired. I had both of my youngest two kids after 40, and it was hard on my body. I’m out of shape and I sit at a desk all day. I wanted more quality time to spend with them, when wasn’t exhausted and irritable.

I wanted to spend quality time with them while they were still young enough to want to hang out with me. Those of you with older kids know what I’m talking about. I also a grown son, so I know all the different stages the kids go through. At some point, they just want to hang out with Mom and Dad anymore.

Now I spend every day with them. We face challenges together, and we’ve bonded in significant ways since untying the docklines.

Hanging out in Iles des Saintes, Guadeloupe.

Health Benefits

Healthwise, I knew I needed a more active lifestyle. Sitting at a desk all day, five days a week, for decades is simply not good for our health. The sailing lifestyle has given me opportunities to live a more physical, hands-on life.

From swimming, to hoisting sails, to just the moving about the boat all day has already helped me build back some muscle. There’s also a sense of accomplishment in this hands-on lifestyle that you don’t get from spreadsheets and finance meetings. Scrubbing decks, hand-washing clothes and dishes are just a few common tasks on the boat that give me satisfaction.

These are tasks I wouldn’t have had time to do in my former life. I wouldn’t have enjoyed them if I had to do them because I was always in a hurry.

I also now have time to unwind, decompress, and truly appreciate nature.

Whether it’s a beach, a deep wood, or a mountaintop you’re dreaming of, each achieves a similar result.

Jolly Harbour beach in Antigua.

New Challenges Replace Old Ones

New challenges have taken the place of old ones. Now I can geek out over trip planning, weather routing, maximizing sail time on our island hop, and other related tasks. My husband enjoys learning the electronics of the boat, mastering the maintenance of our diesel engines, and troubleshooting a gazillion different challenges that come our way.

The sailing life is not a problem-free one. When you walk away from suburban America you are giving up a set of frustrations for a whole new collection of challenges and frustrations. The difference is that these are new challenges, which make them fun in some ways.

Another big change is that we are living independently and don’t “report” to any bosses out here. We are the bosses, the decision makers. We live and die by our own choices. And for some people, like us, there is a sense of freedom in that.

The first time we went on an overnight passage away from land, it was scary. It was also liberating. Up until you actually do it, there’s this unspoken question hanging in the air: “Am I actually brave enough to go through with this?”

When you answer that question with a yes, you’ve just won a mental battle that changes you forever.

How We Got Here

I’m sure you’re wondering how managed to afford this lifestyle. I mean, its why most of you are here, right?

Single Mom Struggles

Believe it or not, when I first discovered this dream of living on a sailboat and traveling the world, I was a single mom with a job making $65k a year as a financial analyst. I was deep in debt, dodging creditor calls, and barely making it paycheck to paycheck. My son was in middle school and he was struggling.

I was afraid of losing my job because of needing to leave work to deal with his issues. Not alot of protection for employees in the place that I lived and I was afraid I wouldn’t be able to provide for us. I started looking for new ways to make money, including trading stock options.

In my research, I picked up a book called Live on the Margin by Nick O’Kelley and Patrick Schulte. I thought the book was about trading options, and it was, but the first five chapters were actually about the liveaboard lifestyle, and its many benefits.

Something clicked in my head.

The Birth of a Dream

I was immediately in love with the idea, and decided right then I would find a way to make it happen. At the time, it sounded preposterous for someone like to me to plan to live on a sailboat. Why?

  • Zero sailing experience
  • No engine maintenance skills
  • No money to buy a boat or even pay for sailing lessons
  • No adults in my life to sail with

At the time, I had no earthly idea that my career would take off like it did. I firmly believe that it happened only because of this dream of mine. Every decision I made was altered after I decided I was going to succeed at sailing away.

Let me give you a little advice. If you want to be successful at anything, it starts with a simple decision: don’t give up until you get what you want.

This dream of sailing away sustained me and gave me hope for a better future. I didn’t learn to trade options from that book, although I did learn to trade them from the incredible team that runs my brokerage, Tastyworks. They have a program that’s completely free and broadcast every trading day called Tastytrade.

I watched the show and practiced with my own meager funds I could cobble together until I finally learned how to successfully sell (or write) options. I trade the market on most days: not as a day trader, but you could say its more of a swing trader style.

Radical Decisions = Radically Different Life

So how did I get from single Mom financial analyst to married Mom of three and Chief Financial Officer of a $100M+ company?

Simple: I started making different decisions that I had made in the past. I took risks. I switched companies four times in six years, and was promoted at three of those companies while I was there. And then I stopped buying things. Furniture, knick-knacks, stuff that I would later need to get rid of.

After getting married, we bought a house that appreciated in value. We sold it. We bought another house that appreciated in value, and sold that one. Those profits super-charged our savings coffers.

Radical moves. We never looked back, only forward.

Eventually we saved enough to buy our boat and we sailed away. No regrets, no hesitation.

To the Average Jo Who Wants to Sail Away

I’ve heard from a lot of folks who consider themselves to be an Average Joe or Average Josephine who truly don’t believe they can ever save enough to sail away. I’m here to prove them wrong, and it is my hope that I can convince each and every one of you that YOU can have your dream of adventure.

It IS within your grasp. You just have to start making different decisions. And more importantly, you have to believe you can do it.

I hope this site will give you ideas on how to restructure your finances, improve your income potential at work, and ways to supercharge your savings so you aren’t stuck in a rut until you retire.

I don’t want to mislead you. I’m not wealthy. I don’t have enough money to sail away forever.

I’m not retired. Over the past several years I’ve learned to take big risks. Walking away from a well paying job that I enjoyed (as much as you can enjoy working for someone else) was a big one.

But it was worth it.

If I start all over again from scratch after this 1-3 year sabbatical is done, it was still worth it. This experience has been life changing for me and my family, and the value of it is priceless.

Learn More

Are you ready to sail away or go on the adventure of your dreams?

If you want to learn more about how to have an experience similar to mine, join the 9 to 5 Escape Club. Exclusively for the “Average Joe”.

I’m going to dedicate some time every week to dumping all the knowledge that I have on personal finance. I’m doing this because I want you to have the tools to live your best life. I also want you to share your experiences for the rest of us to learn from, including the good and the bad.

When you sign up to join the Club, you’ll also receive an invite to our exclusive Facebook group where you can chat with others who are going through the same steps that you’ll be tackling to overhaul your finances and get started on your adventure planning.

The adventure starts HERE:

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