It started with a casual conversation about retirement, something that’s been on our minds a lot more recently, and evolved into an exercise of financial what-if models to determine our shorter term options. We had been talking about it for only two to three days before James created the Sailing Adventure folder on our shared drive.

With that minimal structure in place, I proceeded to use my project management and OCD strengths to initiate several other lists, to figure out exactly what we need to learn, the path to living on a boat, whether we want to, the timing of big events, the cost of this idea, the definition of the idea for each of the people involved, and what we need to know to get there.

Sailing enthusiasts may be laughing at my word choice of “exactly”, since with sailing as well as with other adventures, plans can’t be followed exactly. You set a course and have contingency plans, and make sure you know enough to be able to react appropriately and safely when things don’t go as expected (when, not if).

As we refine the goals, the path, and the steps that will guide this journey, we will share a glimpse of the effort, the ah-ha moments, and tools that help us along the way. And we’ll provide this information through three different lenses, those of the man with the sailing dream, the woman with the adventurous spirit, and the easy-going boy who can sink his teeth into any idea that has the potential to be an epic adventure.

Twenty years from now you will be more disappointed by the things that you didn't do than by the ones you did do. So throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover. - Sarah Frances Brown


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Written by Deanna