Why? It’s a good question! It’s something Melissa and I have dreamed about for years. I’m not sure exactly when Melissa became interested in this pursuit but I suspect her desire is greater than mine at this stage. I’ve been dreaming about this for decades. I distinctly remember reading EVERYTHING from the Dashews and if you know their work, you know that Steve is rather wordy! Needless to say it’s been years of dreaming. Though I’m under no illusions that this will be an easy transition.

We’ve been building to this, in our own way, for years now. We selected our boat with an eye on the initial years of a cruise…with kids. While it’s no blue water cruiser, we found the build quality, cockpit, layout and systems sufficient for what we anticipate our needs will be in the first few years. If we make it that far and still love it we will reevaluate our needs and select a boat more appropriate for that expected lifestyle. For now, our Marine RV should be sufficient for the coastal cruising/milk run lifestyle that we’re currently planning on…a lifestyle conducive to living on a boat with young children, a dog and trying to keep expenses under control. Simply put, our family’s capabilities do not exceed that of our boat. Yet. 

Most of our financial decisions for the last decade have been made with an eye on this future. We didn’t expect it to be doing it at this age (more like 45/50 than our current 40/45) but here we are. And we’re ready. We think. Sorta.

I’ve read the blog posts, scrolled through the ‘Gram feed filled with gorgeous shots (#kids4sail!) and YouTubers who have great skills and make it look amazing. And I look forward to that. But as a lifelong sailor, a decade of boat ownership, at least 2 decades of heavy pessimism and a parent to 2 young kids, I know this isn’t gonna be easy. Layer the global pandemic on top of this and I really truly wonder if we’re doing the right thing. The honest truth is Melissa and I have both felt the universe sending us numerous signals and we finally asked, if not now, when? If it weren’t for the pandemic, we’d be THRILLED with the timing. We’ve got two kids who are both enthusiastic sailors, love living aboard the boat and still crave time with their parents. Melissa and I are “young” and “fit” enough to still do some cool shit physically, my FX trading career wrapping up after 18 years, the right boat for our first adventures, each losing a parent…it’s time. I could write a much longer post about why we shouldn’t go. Truly. I know it’s not gonna be easy. At all. There are so many issues and hardships we expect:

Weather/Conditions conspiring to make passages harder, longer, more unpleasant

Motoring our sailboat at least 80% of the time, rather than using our sails to sail our sailboat

Homeschooling 

Pulling my kids from a great school

Losing the French Immersion track my oldest was in

Seasickness

Having a dog. Why on earth would you take your dog?

Stuff breaking

Unexpected costs

Breakdowns

Living on a boat with 2 young children, a super shedding dog and a spouse who views the world a bit differently than me

Things that stop working

Laundry in a bucket. I’ve worked too hard to do laundry in a bucket, right?

Hand washing dishes, 3 times a day, every day 

Managing border crossings in a global pandemic

Keeping my family safe and healthy

Stuff breaking

I’ve read through this list now a number of times. I could easily double it. Why would we give up our great, easy life? It’s certainly not because we want more. We’ve got enough. We’re incredibly happy. I think we’re looking for something different. Money won’t buy me more time with my kids. Getting that promotion won’t make my wife desire me more. Right, sweetie? With risk comes reward…or spectacular failure. Most of the great trades we’ve made in our life have involved hard decisions and not come without risk. I mean, hell, we moved to Canada! This is definitely a risk, but we’re hardly betting the farm on this. As I’ve explained to Oliver, if it doesn’t meet our expectations, we get to come back home! And we’re really happy here!

So why go? Why not? The timing is right for us. We could push our departure a few years later. I could work a few more years, stringing out a career that I’m no longer enjoying, Melissa could reenter the workforce and try to restart a career for, what, 2 or 4 more years? It seems rather disingenuous to both ourselves and our employers. Our kids really do love the boat and their time on it. We already see Oliver’s roots to our community getting deeper and stronger. While we don’t like the idea of tearing out those roots, we think the risk/reward favors leaving now rather than when he’s 10 or 12 and further rooted. We hope the experiences and adventures will outweigh leaving his friends, home, bedroom and school. I learned years ago that “hope” is not a strategy or, at least, a terrible plan. And I think that’s what scares me the most. We’re hoping this is the right time for our departure. We’re hoping this is the right move for us. We’re hoping we can manage a global pandemic, sailing from country to country with borders that were recently closed and may close again. We’re hoping this isn’t financial hare kari. We’re hoping we like it, the kids like it and dragging a dog along won’t be horrific. At some point I think you’ve just got to take the risk, say fuck it and go sailing.

So, fuck it, we’re going sailing.