Why living on a sailboat is not what you think

Post updated May 17, 2018

If you ask some people what “sailing life” or a “cruising lifestyle” means, you might hear something like this:

It means living on your sailboat in the summer and cruising around. It means sun, sand, and surf. It means repairs and maintenance are as simple as dialing a phone number. Its bikini bottoms and tan lines; dolphins and prepared lunches.

It’s a vacation life!

While these things *technically* can be true, they aren’t the whole picture. Perhaps if you’re a one-percenter with a 6 or 7 digit income and a LOT of annual vacation days to use up, then yes… sailing is all of these things. I can only guess that if you’re liveaboard and money is no object, sailing is likely a vacation to you.

The rest of us have to live in the real world.

So while it’s fine to get caught up in the Pinterest-perfect landscape depicted in media and by our well-to-do friends on what a cruising lifestyle is all about, there is another reality out there. The working liveaboards.

And we understand, usually by necessity, the true realities of owning AND living aboard a boat. Liveaboard cruising certainly can have a lot of the aspects of what a vacation looks like… but it is definitely NOT a vacation.

What does a liveaboard lifestyle look like (if you still have to earn-to-live)?

Well, it looks much like your landlubber life would. Let me put it this way: vacations are meant to give a person respite from the stressors and pressures of their “real” lives. They’re only meant to last a short time, and are – in essence – an escape from your usual reality.

I live on my boat. Full-time.

There is no escaping my reality, because this IS my real life! I’m here rain or shine, winter or summer; when things are going well, and when things are breaking all around me.

The perks of living aboard

What a liveaboard sailor DOES do, though, by moving onto his or her boat is transform the traditional ‘work-work-work-VACATION-work’ cycle into (hopefully) ‘work/enjoy – work/enjoy – work/enjoy’.

We don’t stop working, or dealing with stressors, just because we live on a sailboat. However, what we have done is situated ourselves so that the very things that cause us stress are also those things that bring us our greatest enjoyment! We’ve merged our vacation life with our “real” life which, I think, brings the two into a harmonious balance.

It’s similar to that advice you get when people say “choose your dream job, and you’ll never work a day in your life.” Except I think this is an oversimplification. You will work. Every day. And it won’t always be fun.

But what you’ll find, when you’re working, is that there is a extra bit of motivation and keenness about what you’re doing that doesn’t exist in “some job” you work just for money.

Not all the work is fun. But all of the work IS rewarding… because you are working directly on something that gives you pleasure.

Living the cruising lifestyle on a sailboat is something you pick because it’s your dream. Your passion!

Yes, it causes you plenty of hardship and stress: things break, storms rise up, and sea states make you ill and lose sleep. Not to mention the bills for supplies, fuel, equipment and repairs seem endless and, sometimes, insurmountable.

But then, I ask you, if that’s the price of living your dream, would you do it? All things being equal, I’m thinking you would. In a cold minute.

Accept the whole truth of your dream, and you’ll never be disappointed

I think what you realize when you start actively pursuing something important to you is that… life is happening now. Every second. And every second you spend NOT working on or towards that one big dream of yours feels like pain.

Not the “no pain no gain” kind. The “what am I doing with my life” kind.

I’m not trying to bum you out with this, but I think it’s important, as it is something I thought about a lot when we made the transition to this life. I had to ask myself if I was ready for the realities of living on a sailboat, even though I wasn’t fully aware of what all those realities were going to be. I had to reconcile the motivation I had to live this dream with my willingness to overcome any hardships that would arise by pursuing it.

These aren’t always easy questions to ask yourself… especially when you can’t truly know how it’ll be, until you do it.

Pic of Josh (right) and his little brother on their family sailboat

How a dream defines a lifestyle

Up until the decision to move onto a boat, I had no specific dream that I was working towards. Life was more or less just happening to me. Josh had dreams, though; and I told myself that if I wasn’t going to work towards any personal dreams, I would make damn sure I did everything possible to support him in his.

And this dream was his biggest dream… until the day I made the decision that it could be OUR dream.

Walking the docks of Granville Island one fateful day, I concluded – unprompted – that what I wanted was to live on a sailboat. Not for him. Not for anyone else. But for me.

This is the truly important part of this. Some people are willing to flip their entire life on a gamble that they MIGHT enjoy something. Some people need to “test the waters” and try things out slowly, to make an informed decision. Others may never be truly ready to make the leap, and will put things off until retirement or some other arbitrary date.

This isn’t meant to sound like a criticism of any of these thinking behaviours, but it’s important to know which one you are. For this dream, I discovered I was willing to take a gamble. I wanted an adventure, and I was willing to give up the life I knew for the unknown. That was all I needed to move forward.

It’s never too late to have new dreams

Once the decision was made by us both, everything changed. The money I earned from my job suddenly had a purpose. There were suddenly things to be learned, work to be done, balls to be set in motion. And it made things feel… different. My life suddenly felt intentional!

I mean, isn’t that why we have dreams? They are challenges to rise up to; they’re ways of living and becoming more than we are now. Of proving yourself, to yourself.

And dreams can change! They can rise up and recede like tides, or come flying out of left field and clock you over the head. Or, they can be deliberately chosen – adopted from nothing, like a stray dog. And like an adopted stray, they can become that thing you find yourself living for everyday, and loving more than anything in the world!!

We are driven by the challenges set before us by our dreams, even if we sometimes suffer in the process.

So why do we do it? Because the rewards we earn are not just to be found at the end of some goal post… they’re experienced every day. In every moment you spend working on your dream. Which, to me, is better than a vacation.

Thanks for reading. Please feel free to leave any questions or comments below. I’d love to hear from you!

Stay awesome,

  — Morgan