This sailing season is dwindling down and once again we are faced with a million and one questions about what our future holds. For the longest time we were ok with flying on a whim and making decisions at the latest possible moment, but things have started to change a bit. We have two sets of close friends that have just made very “grownup” decisions that change the way they live. The one couple recently sold their long-running businesses that they had given a 1/4 of their lives to set up, and are now retired. And the other friends are making a business choice that will commit them to one place for the next 5-10 years. This decision will also hopefully set them up financial for the rest of their lives. When close friends that you love and look up to start making life-altering decisions, you start to look at your own life and wonder if you should be doing something similar. 

   Should we be trying to get financial stable. To “grow” our own business? To commit to something we love that will also earn us a living? Or should we keep island hoping, doing little jobs that can sustain our lifestyle, and see where that takes us? Should we head south this hurricane season and go chill with a ton of other boats in Grenada? Or should we try and find a land-base where we could start focusing on a business? Do we currently have the funds to invest into a “start-up”? Or do we need to work for the next year to grow a nest egg for that? Do we have enough money to keep sailing, and how low are we willing to let our savings get?
   These are all the questions that are plaguing us as we try and fall asleep at night. And I totally realize that these are “first-world” problems/questions. I am completely thankful that these are the questions that bug me at night and not ones that some other people in the world face, like can I afford food for my family tomorrow. But this is the position that we are in, those are the questions that we have, and soon, very soon, we will have to put on our grown-up pants and make some decisions that will take our family one way or another.
   But for now we are procrastinating making any definitive decisions, and I am whole-heartedly procrastinating having to put pants on. 
   But as far as VERY vague plans go, we have thought of heading to Grenada for hurricane season. However we have also thought about going back to live in the Dominican Republic. As you can see the dilemma, these are in completely opposite directions! We could sail to Grenada, haul out and fly to DR, or we could face the Mona Passage a fourth time and bring our boat back to DR, or we could forget about DR and see if there are any opportunities for us in Grenada. All confusing, and no matter how much we discuss these options we don’t ever seem to make much headway.

But at least, for now, we have this view while we debate