Sharing Our Stories, The Big Decision Q&A

Should I quit my job and go cruising? Kathleen Watt responds


My husband and I are thinking of living aboard a sailboat in four to five years from now. His daughter is grown and just purchased her first home while my daughter is a freshmen in high school.

I suppose it is harder for me to take to the idea of living aboard because I have a really great paying job and I feel I need to help my daughter with college. I am only 39 so leaving my career is harder than I thought it would be. Any advice for me? My husband is 47 and more than ready to leave tomorrow. He is self employed and can build or fix anything so he will not have a problem finding work along the way of our adventure.

I look forward to hearing from you if you have time or advice.

– Judy and John


(Women and Cruising sent Judy’s question to several of our friends/contributors for their thoughts. You can read Beth Leonard ’s response here, and Sherry McCampbell’s here. Here is the third response we received, from Kathleen Watt.)

Kathleen Watt responds:

Dear Judy,

When I was asked if I would be interested in responding to your question, I not only wanted to, but felt compelled to do so.

You see, my story is not unlike yours.

I moved aboard and went cruising at age 38.

I had a daughter who was a sophomore in high school, a great, well paying job, and was about to complete a university degree that I had worked long and hard for, while working full-time for many years.

I was not a boater (I got pretty seasick), I was not a water person (terrified of deep water and not a strong swimmer) and I had never sailed before.

Here’s where things are different.

I was divorced, my daughter lived with me, but spent summers with her dad. I was not married to the man I moved aboard with (although madly in love, we were still dating) and had little savings of my own. I was, and always had been, financially independent. (I had a professional career that earned more than my ex-husband.) The thought of being dependent on ANYONE, including previous spouse, much less boyfriend, was more terrifying to me than deep water…well almost.

But…the love of my life, my then-boyfriend, Brian, always dreamed of doing this sail around the world. He had come out of a nasty divorce, was at a point in his career and finances that he could be away for quite awhile. I knew this was important to him, but I just didn’t think I could go, no matter how much he wanted me to, for all the reasons mentioned above. I told him he would have to go without me. I wouldn’t have asked him to stay because I felt he needed to do it for his own peace of mind.

Then, the strangest thing happened…

…my daughter found a boyfriend in New Orleans during her summer trip to her dad’s. I am from there and still had many family members of both sides living there. She called and asked if I would get upset if she spent the school year with her dad and summers with me, instead of the reverse. Her dad and I were, fortunately, good friends and I had no problem with that, other than missing her, of course. So, here was the big dilemma. My biggest reason for not going with Brian had just made a decision that freed me up to go. Brian had already bought a boat and left for the Caribbean.

I thought long and hard about what my decision should be.

I decided that this relationship was truly something special and I didn’t want to lose it.

School could wait. I supposed I could accept dependence for, at least a while, to try this all out. There would always be a job somewhere if I came back. I got certified in scuba to get over my fear of deep water (it took a year for that to work before my heart stopped trying to leap out of my chest when faced with the jump into the ocean.) I got a good stock of Bonine and learned to sail. This was probably the hardest decision of my life and I count it as one of the most important, as well.

Was it the right one? Let me tell you how the story ends.

In Moorea We had a glorious 4 and half years of sailing around the world.

We completed our circumnavigation in 1998 after 40,000 miles and 37 countries. We hiked the Inca Trail to Machu Piccu, we climbed the peaks of Bora Bora, we parasailed off a mountain in New Zealand, met black pearl farmers in the Tuamotus, sat with chiefs for dinner in Fiji, and watched game in reserves in South Africa and so much more.

That’s just the land stuff that cruising allowed us to do. We also saw the most incredible sea life in three oceans, we swam with reef sharks and chased grouper in underwater coral caverns, we dove on a wreck in Vanuatu, caught lobster as long as my arm and saw phosphorescence leaving a glorious green light in the water as we sailed on moonless nights and watched a whale give birth in the sea off Madagascar.

I could write a book on the wonders of this lifestyle. The friendships that we developed in anchorages will last a lifetime. But, most importantly, we shared memories that few in this world will ever experience, and we did it together.

Brian and I got married on the deck of our boat in New Zealand two years after sailing together. There could be not tighter bond than the relationship that weathers a cruising lifestyle. It relies on trust, friendship, teamwork, respect and love, to a much higher degree than you ever have ashore. It’s been 15 years now and we are still crazy about each other. I think cruising brought us so much closer than we ever could have believed.

This has been the long answer to your question, but here’s where it gets real.

Six years ago, we decided to head back out, bought a new boat and sailed it back from France.

We were back for two weeks when we got rear-ended in a car accident that tore Brian’s carotid artery and caused a massive stroke. It has been a long road to recovery. Brian, my larger than life, brilliant husband who could do anything, lost the ability to walk, talk, read, speak, or comprehend. It took a long time, but now he can walk with a cane, speak in 3 – 5 word phrases, got most of his comprehension back and can read a bit.

Why am I telling all of this to you…

…what does it have to do with your concerns?

Just this…the one thing that always brings a smile to his face is our reminiscing about cruising and how lucky we were to have done the things we did. If we had waited, if I had given in to my fears, concerns, etc., if we had decided to wait until all things were right, it may not have happened. Our greatest pleasure, our happiest times took place on that boat. We are still madly in love, but incredibly sad.

Brian and Kathleen Watt We lost so much. But, we have so much to be thankful for, as well. Those memories are incredibly precious.

I am thankful every day that we didn’t get caught up in life and lost the opportunity to live the life we have.

We have a pretty good life now, considering…but, our life onboard Renaissance will always bring back the days of happiness, strength, excitement, enchantment and contentment.

So Judy, I hope my tale has given you a different perspective on things.

Don’t lose a chance to incredible experiences for what seems important now…like a great job. Your daughter will move on to college and make her own life.

My daughter LOVES the fact (and still talks about) what neat places and things she got to do on her summers with Mom. Did I miss her…you bet! But, I think she has a better life and a better Mom for it.

What cruising did for me is immeasurable. I am stronger, more confident, and capable than I ever dreamed. When we came back, I took on a new career that was infinitely better than the previous, completed my university degree, and even got a helicopter pilot’s license at age 50.

So, for all those things I gave up to go cruising, I was paid back tenfold in being a better woman, a better Mom, a better wife and a better friend.

Sailing really does bring you back to what’s important. I am not sure how I could have weathered the storm we faced after that accident if I hadn’t been forced to prove myself on the water.

I didn’t mean to write a book to you, but your concern resonated with me so deeply. Good luck with whatever course you choose.

What’s meant to be will be. But, don’t be afraid to take that leap if given the chance. You won’t regret it.

Regards and best wishes to you,

Kathleen Watt

About Ask Your Questions

When we receive a question from Women and Cruising readers, we send it out to women who we think might have relevant experience to share. These women often email the questioner back directly, but if everyone agrees we will also post the questions and answers/responses here in the blog. We may change the name or some details of the question to protect the questioner’s privacy if requested.

Beth Leonard and Sherry McCampbell also responded to Judy’s question. You can read Beth’s response here, and Sherry’s here. We will be posting others responses as we receive them.

If you have thoughts for Judy on her big decision

Email or leave a comment below. We will send your response on to Judy, and may post it here on the blog too if you agree.

Do YOU have a question for Women and Cruising?

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1 comment to Should I quit my job and go cruising? Kathleen Watt responds

  • Lisa

    What an inspiring story- I just finished it and I’m crying. Its January now and I am planning to leave with the Love of My Life to go sailing for an indefinite period of time in May. I am “giving up” a job as an elected judge, have held it for 17 years. I know I (we) must seize this moment and reading your story only validates that belief.

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