3 reasons I'm afraid to sail away

I Worry About The Unkown

My youngest son, Charlie is 1.5 years old, and still wakes up fairly often in the middle of the night. Whenever I'm in his dark room, standing over his crib, shushing him back to sleep, I think about how happy I am that we are not living on a sailboat.

I think about how nice it is that I'm not in a strange place, a thousand miles from home. I think about how comfortable my house is. How it can't sink. I think maybe I don't want to sail away. Maybe we should just stay home. It's SUCH a comfortably tempting thought to think.

But when I really embrace this idea, it falls apart. So we don't go sailing. Then what? Do I go to work and keep up with the Joneses? Two weeks vacation once a year. Is that it? Is that what I want to do with my life? Absolutely not.

Do I want to look back on my life and think "I chose comfort and familiarity over living the life I really wanted." No way.

I Worry About Money

I spend most of my time worrying about money. It's the most pressing issue, and in a lot of ways it's the easiest to solve compared to intangible things like "the fear of the unknown."


My concerns start with health insurance. When we were younger, life didn't cost as much money. We needed food for two and gas money for the boat. That was about it.

Now we are a family of four, and its our responsibility to look out for the well being of our children. I consider health insurance for all of us to be a necessity.

I'm hoping that I'll be able to keep my current job in some form. Just in case that doesn't work out, I've started a web design and management company called Wowie.co (please check it out, and tell your friends). The company has been really successful so far, but it's still a candle in the wind. I'm also experimenting with revenue streams from this blog, which I will share updates on in a later post. We also plan to rent out our house.


While I worry about money, it's not a reason to give up the sailing dream. Cruising has provided me with many skills (self-confidence, problem solving, budgeting) and even opportunities. My current job and income is directly connected to our 2007-2009 sailing trip. So who knows. Maybe this new adventure will result in new income streams I currently can't imagine.

I Worry About Uprooting My Family

I have a lot of wonderful memories of growing up. My parents have lived in the same house for as long as I can remember. Living in a house provides a lot of interior room to run and play. I remember playing catch with my dad in our back yard. Riding skateboards and bikes in our driveway. I have a lot of wonderful (and horrible) memories from going to school, and there are people here in Muskegon that I've known since the first grade.

I'm afraid to pull my kids away from the wonderful childhood I had. I know Hobie in particular is going to miss our house. He is going to miss our cats (which we are going to have to find new homes for).


On the flip side, I don't know how great it can be to grow up on a boat because I didn't experience it the way my kids will. They will make their own special memories. They will see and experience things that other kids don't.

Ultimately, I don't think there is a "right way". I think (hope) that my kids will look back on their childhood and view it as "normal" because it is simply the only one they know. I mean, the idea of growing up in India is totally exotic to me. But to the kids who grow up there, it's just normal.

You Only Live Once

Whatever my fears, I always come back to two things:

1. My life is going to go by faster than I would like it to.

2. I don't want to spend my life working.

I'm not opposed to work. I'm a straight up workaholic. But I'm always asking myself "when I'm old and looking back on my life, what do I want to see? A life spent working, making money? Or a life spent making memories, experiencing as much as I can of this amazing world where we live?


I think everyone tricks themselves into thinking "there will be time later." But... there won't be. This is it. Life slips by like sand through your fingers. Ask any old person and they will say "each year goes by faster than the one before."

I can't help but feeling life doesn't really want to be lived. It's like the buzz of a refrigerator, the ambient noise that no one notices until it suddenly cuts out. It's easy to take for granted.

You have grab life by the throat. Don't let it slip away. You only get one shot, so make it count.