Kris and I packed up some notebook paper and a couple of reference books and went looking for a coffee shop one Saturday morning with the intent of creating a plan for our life. It very quickly started to feel like a business meeting, so we surrendered to the moment, threw everything back in a bag, went to Kris's office, which was nearby, and started drafting our ideas with a more formal approach.
The s/w firm I'm currently working for (look for this to change soon) employs an agile development approach and at the end of each two-week sprint we do a post-mortem exercise to review what is working well and what isn't. The approach there is to have each individual write down on post-it notes the things they want more of, less of, and stay the same. Kris and I took the approach of writing down every discrete item we were thinking about with regards to our desire to make the move to a cruising life.
We took all of the notes and stuck them up on the wall. There were about sixty notes posted all over and the next step we took was to begin moving them around and arranging them into groups that made sense. We ended with three groups: business/financial concerns, transition tasks, and knowledge and experience we need to gain over the next five years.
After this we pinned up a couple of 2'x3' sheets of paper on the wall, added headings to the top and ended up with four categories, having split the business category into a Portland living-aboard phase and an underway phase.
The next step we have to take is to organize all of this into a timeline. So, that's where I will be this coming Sunday morning.
Oh, yeah, the intial phase involves selling a bunch of stuff, including a house, a condo, a BMW Z4, a pick-up, and a bunch of smaller things. I took the first step and posted a surfboard and a bike on Craigslist. The bike went the first day.