Almost Fearless

The Slow Death of My Dream to Sail the World

In 2008, I had a conversation with my mother that went like this: “Mom, I’m quitting my job to become a writer.” “WHAT?”


Just a month before I was scheduled to leave, and after I had put in my notice, I got a job offer for $100/hr consulting work. 1-2 year contract full time. $200,000 a year (software job, and here’s the thing about consulting, they pay you more when the job is really terrible). All I had to do was live in Texas. And do I job I had left a few years earlier. That’s it. Not that bad really.

I didn’t do it. I leapt. On reflection, it was really insanely risky because even though I ended up making it, I had no reason to have such blind hope. I could have just signed up for a good yoga class, some therapy, a weekly massage and figured out how to make that career work. Instead I threw it all away to become… a writer. A writer! How much do writers make? Hint: not $200K a year.

Anyway I’m happier now. I love my life. But that recklessness is still in me. I do feel like this is true: if I put my mind to it, anything is possible.

Having a second baby changed that.

This is how it happened. I have been talking about sailing for years. Drew barely wanted to do it, he was daunted (rightfully), but I persisted. I pointed out people who did it with little kids. We saved money for a sailboat. I read books and clipped passages to read to Drew. I’ve been planning this for years now. Then I got a book deal — it was sealed, when I turned in my final manuscript in June 2014, I would get a lump sum payment from my publisher. That was our sailing kitty. We didn’t announce it, but we quietly decided that yes, absolutely yes, we were going to sail. Maybe it would just be the Caribbean or the Mediterranean for a season until we got our bearings. Maybe Cole and I would fly to the next destination while Drew did ocean passages with friends. Maybe it would just be for part of the year, but we knew enough families with small kids who loved live-aboard sailing, that we were convinced we could make it work.

Then I had Stella.

I learned something about my husband this year: he has ADHD. Since coming to Mexico we’ve had better access to pharmaceuticals  so he finally found a drug that works: Concerta (it’s awesome). We also found out that he isn’t a 15 mg dose kind of guy, but more around 50-60mg. We had been doing it wrong for years. Suddenly Drew’s difficulties concentrating were abated. It was grand. I was really happy for him.

For adult ADHD sufferers, age can play a factor. It does get worse and worse the older you get. It’s also often triggered by having children. The buzzing distraction of little ones running around to the adult with ADHD is like the equivalent of not sleeping for 48 hours. It wears down your defenses and where you were once able to cope, you’re suddenly forgetting things, driving distractedly (almost getting into accidents), unable to complete tasks, feeling overwelmed and irritable.

Drew was so distracted when we had Stella, I asked him to get soup and juice for me while I was in the hospital (all I was able to eat) and it took him three trips to the store to finally come back with a can of tortilla soup (no spoon) and V8 (which I have never had in 13 years of knowing him). It’s hilarious, but also, oh my god, what has happened to my husband? It’s adult ADHD. It’s tricky.

Still, we even looked at boats here in Mexico. We visited the marina. I did more research.

The first few months were really rough, but I think we’re back to normal now. But here’s the thing: sailing is stressful. Navigating into a harbor at night, with an ADHD captain who loses focus under duress is just not going to work. Of course, I could sail the boat, that’s not a problem. But these things add up.

I was heads-down charging through with this plan, meanwhile my life was changing around me, it took me a while to come up for air.

There’s my little babies. They don’t really care to be on a boat. They would like to be in a playground though, with other kids. Or have all their toys. Or get to go outside and play in the yard without being tethered to the mast. We could do it… but should we?

No. Not really.

When I had Cole I swore I wouldn’t let my life be changed, but I was wrong. It’s a different kind of leap, the one you make for your family. It’s just as scary and terrifying as starting a new career at 30, it’s the choices you make for the people you love. You leap. You hope it will work out. You’re never the same.

I’m so stubborn. I really, really wanted this. But then, it just dissolved in my grasp and I let go.

Goodbye sailing. Hello my sweet family.

Maybe we’ll rent a boat one day for a week-long vacation where we motor around and island-hop — when the kids are bigger, and Drew has lots of Concerta. Until then, I’m content to admire the sailers who are making it happen.

Photo: katiew

Christine Gilbert

I’ve been dragging my husband around the world since 2008 always with the promise that, “Yes, Drew there will definitely be hammocks there.”



  • Such an brilliant post. I just came over here to drool over the iced coffee horchata, and found myself enthralled by this one. I knew about your sailing inklings which you have hinted at, and had no doubt that you guys would make it work, but I commend you for being flexible on your dreams. I’m sure it’s not easy, but will ensure a much happier existence for you all, and I’m sure your replacement adventure will be even more awesome!!!

  • Life is very good at throwing us curve balls hey. If you’d told me years ago that I’d be married to a farmer I would have laughed and yet here I am. I see so much of my younger self in you sometimes Christine, the relentless energy, the list making haha. Sometimes it’s not about letting go of your dreams. It’s about shaping new ones. Ones that will work for your little family. And perhaps more importantly, finding the space and trust within a relationship to pursue your individual dreams when the time comes. They may not be your original version, they may be a somewhat tacked together, messy version of the original but they can be equally if not more fulfilling.

  • Have you read ‘Around the World in 80 Days’ by Jules Verne? Maybe you can have an expedition like this on trains and ocean liners?

  • I totally understand where you’re coming from. Sometimes it takes more courage to drop a plan that turns out not to be right for you than to keep pushing it. If it’s any consolation, you’re welcome to come spend time on our boat when we sail through Mexico…it will probably put you off squeezing your family into a closet-sized space forever. I mean that. Life on a boat ain’t always sunsets and cocktails 🙂

  • The boats aren’t going anywhere either. Maybe it’s something you do later in life (once you’ve published multiple best-sellers and can hire a captain). Dreams change, I get that. Sometimes things end up even better than the original plan.

  • This was heart-aching reading for me! With the 2nd one on the way I’ve been convinced we can do couple of the big plans we’ve had in mind with the family of four, and that our lives are not going to change “that much”, despite of what everyone has said… I’ve had this nagging feeling that something might have to give, but I’ve been hopeful that maybe not after all. You choosing to let this dream go for now made me even more fearful that the same might have to happen over here. Although the good thing about dreams is that there are always new ones, and choosing your family is not a bad choice at all! 🙂 Great news for Drew regarding Concerta though, hope the pills keep doing their magic!

  • I think it can take us by surprise, the way dreams change or get reshaped. It can be so freeing to just admit that things haven’t gone as planned, but are wonderful nonetheless. What you have now – the independent succes, the healthy, happy family and a solid marriage – that is the real stuff of dreams. It is this story that has me hooked, not the adventures you undertake. I look forward to your next chapter. Stay happy!

  • After you must’ve read “Love with a Chance of Drowning” I can’t believe you were still seriously considering it. I read it a few weeks ago, and feel less interested in sailing the open seas then the little I was before.

    Solid ground is underrated! I’ll also admit, I was a little worried. I mean the ocean, kids. I know if you wanted it, you could do it, but sometimes knowing you can do something is enough to satisfy the little voice in your mind that wanted you to do it.

    At least that’s how I feel about travel now. Could I have sailed 48 hours on the open ocean from Panama to Cartagena? Yes. Do I want to potentially endure 2 days of seasickness, storms, and cramped quarters. Not really. So I flew instead 🙂

    • Ha, funny you say that, because I read it and then really *wanted* to sail around the world in a small boat with just Scott and Ella! (Though that said, it did instill a certain kind of anxiety I didn’t have prior to reading it.)

  • It seems out of all of life’s events, there’s nothing quite like having kids for shifting your priorities. But, although what’s best for them becomes more important than what you once dreamt of doing, I don’t believe that means you have to give up on your dreams altogether, they just have to adapt to your new life. It might not be the time for sailing right now, but there’s always chance of that dream in the future!

  • Sailing the world sounds like one of those lovely pipedreams that, in theory, I’d love to do. In reality, I’m more of the rent-a-sailboat-for-a-week-in-the-BVIs kind of girl. So, meet ya there?

  • This may be my favorite post you’ve ever written, and I’ve been reading your blog since the beginning.

    When I had Cole I swore I wouldn’t let my life be changed, but I was wrong. It’s a different kind of leap, the one you make for your family. It’s just as scary and terrifying as starting a new career at 30, it’s the choices you make for the people you love. You leap. You hope it will work out. You’re never the same.


    And I want to tell you that’s a good message for some of us with older kids too. I’ve been doing things a certain way for a long time. While I was doing my thing, my oldest has developed an absolute passion for baseball. That’s a team sport, not something you can just do on teh road. To get on the good teams, you need to be around all summer. He made Allstars for the first time this summer. Do you see where this is headed? Pretty soon I’m going to be staying at home from March until September, or traveling without him and my husband. Totally not what I had in mind. Totally what I need to do.

    Leap indeed.

  • I loved this post and I think you really have a great blog. I will defiantly visit your blog to read more.

  • What a hard decision. You chose best for your family, and thats all that matters. Don’t give up your dream completely. Once they are 18, you will be itching to try again, and you just might succeed. For me, your entire post is one of a hundred reasons I have no interest in having kids, and never will. I will say this, if I had them, I can only hope I could do what you have done so far.

  • This gave me goosebumps! As a single and childless mid-20s lady, it’s wonderful and enlightening to catch a glimpse of life-with-children and all that it entails. Also, hooray for Drew!

  • Hey, loved this post! I was thinking, it is all about the seasons of our lives, don’t let the dream die, just tuck it away for a little while, and who knows, it may resurface again, just in a different way. You just never know…

  • Thank you for writing this post. I also find myself in a position where I am slowly, painfully letting go of a long-held dream. Your words hit home, “Goodbye sailing. Hello my sweet family.”

  • I remember reading a post you wrote, pre-kids, about your sailing plans – I may have even commented on it but I remember thinking (with kids ages 2 & 4 at home) NO way. But the great thing about sailing is that when the kids are old enough to help, or old enough to be doing their own thing, you can go do it (with a better understanding of ADHD coping mechanisms and drugs). My yoga instructor recently mentioned she’d just returned from a multi-year sailing trip… talk about living vicariously!

  • As you can see, I am catching up on my reading tonight 🙂 I love your blog, and this post is truly awesome.
    ” It’s a different kind of leap, the one you make for your family” – this sentence is sooo true…That is how I feel as well…I also took a different kind of leap, but one that enabled me to be still me, while having my family as priority…That is how I describe living in Norway…Would I love to live somewhere else in Europe or Latin America (where I am from)? Yes, definitely. But I cannot do that now with 2 year old twins that need a bit of regularity, structure and family around. But moving here is still true to me, it is still my “adventurous spirit” talking loud and it is definitely not me “giving in”. I am a Brazilian, from the hot tropics, discovering cold Norway…It is an experience…It is still who I am…

    Lots of love from Oslo:-)

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