Choosing to Sail

 

How do you decide to sell everything you own and move aboard a sailboat? Very carefully... with lots of lists, spreadsheets, and planning. Or at least, that's what we did. :)  

For quite a while we had been actively researching new career directions for John along with a new area of the world to live. I’ve been building my experience in the creative realm over the past several years, which has given me the flexibility to work remotely. So it seemed only natural to think big location-wise. As we explored various possibilities, we began to notice some trends in the things we valued and really wanted to build into a natural part of our lives:

  • Work that we both love
  • Jobs that allow us to put life first
  • Travel and exploration - with more time to do them both
  • More time with each other
  • Living in places with different cultures
  • Memorable experiences in our day-to-day life instead of needing to book plane tickets and time off work twice a year to explore someplace new 
  • The ability to frequently be on, in, or near the ocean

When we discovered sailing by accident and John suggested WE could do it, I thought he was kidding. After all, we're just two little suburban dwellers, not daring explorers! After the initial shock of the idea subsided, thoughts of us sailing across oceans to beautiful islands contrasted with terrifying storms, sunken ships, and creatures of the deep made me think we’d either found our dream life or Pandora’s box. ;) It was 100 times bigger and more daring than any of the other options we had been considering, which made it quite terrifying. So, we surrounded ourselves with as much information as we could, to discover if this seemingly crazy idea might actually be a possibility. It took a lot of introspection and critical self-analysis to determine if it was a risk worth taking.

As we considered the parts of our life we would have to give up, the things that would change, along with the things that would be added, our decision began to take shape. Although we’d have to give up a lot (literally almost everything we owned including our house, and the life we’d already built), the things we would gain included every single thing we wanted most out of this next stage of our lives. Including literally living ON the ocean! From there, moving aboard a sailboat just made sense. 

After making the decision that we were actually going for it, for awhile, each day we’d wake up and wonder if we were crazy. After all, when you're waking up in a cozy bed in a beautiful home, and living a somewhat comfortable life... getting rid of all of that to live on a boat can feel a bit jarring. ;) We’d go over all the pros and cons over and over again, and every time we came to the realization that it was still an amazing possibility for us and something we just had to try. Eventually, the craziness (or morning-after shock, if you will) subsided and was replaced with the weight of the daunting tasks ahead. Time spent lingering on the fence of “will we?” or “won’t we?” shifted to time spent making and working on lists of things we needed to learn and prepare in order to make it happen. 

That's where the magic has really happened, in my opinion. As we’ve dived into the thick of it, each new hurdle and task has proven time and time again that we're steadily inching closer to the life we want to live and the people we want to become. We've learned so much about ourselves and what we're capable of through this process, that I honestly wouldn't change it for the world.  

Although the past year has been filled with seemingly endless research, preparation, and work on all fronts, those thoughts of sailing to beautiful islands are starting to return in more clarity than ever before. We are so excited to be on this journey and almost ready to set sail. And even if this grand adventure turns into a colossal failure, it will have been worth it to have tried. It would be the regret of a lifetime to not try to live our dream!

So here we are, on a little sailboat with our dogs, ready to explore this beautiful world.