Sometime July 2021 everything crystalized into a single thought: We should sell everything, buy a sailboat and live on it.
Dialing back time quite a bit.
I've had a goal for decades to one day retire on a sailboat and travel the world. Throughout these many years, it was always a retirement goal 10, 20, 30 years into the future. While waiting for this future to arrive, we worked to eliminate debt, pay mortgage(s), utility bills, the various hobbies and activities necessary to pass time over decades, and if everything was balanced responsibly, then elimination of debt, plus savings, plus retirement investments, plus (maybe) social security and a house sale should be able to finance 13 years of enjoyment before I statistically kick the bucket.
Professionally I can't complain. I've done a good middle-class job of entering into the Director/VP layer of IT, but truthfully, information technology has never triggered any enthusiastic feelings in me. More so, I think my overwhelming introversion and inherent objectivity made it a natural fit, though not an enjoyable one.
Maybe it was COVID, maybe age (I'm 42 mid-2021), maybe a growing realization that life isn't supposed to be a carrot on a stick, or maybe it was a mix of these and many other small conditions leading to me meeting my wife after work one day in July with: "What do you think about getting rid of everything and moving onto a sailboat?"
Absolutely, let's do it!
Simple and entirely unexpected. At this point, we live in South Dakota, my wife and kids have never set foot on a sailboat, but this led us down a path we have yet to figure out where leads. Early August we listed our house for sale, by late August 2021, we had a list of sailboat requirements and preferences identified. These included a U shaped galley, two heads, ketch rig, large diesel and fresh water capacity and a desire for center cockpit. By mid September after a few weeks of looking around, I stumbled on Aries, a Shannon 43 ketch from 94 located in Chicago, seemingly in good shape. The only bullet on the list of wants missed was the center cockpit. But as far as cruising sailboats goes, this Shannon was high on the candidate list.
By mid October we had sold our house and inspected Aries in person, and I had out of nowhere lost my job early October.
No house, no job, a sailboat in Chicago where it was going to stay over winter. If this wasn't stressful enough, we have two daughters ages two and four at the time, and oh, as mentioned, very little sailing experience.
How you process your experience, what your motivations are, and your confidence in the face of uncertainty is unknown to me, I just know myself and to a lesser degree my family. The loss of income probably triggered a need for stability and I spent the next weeks networking and establishing contingency plans, in other words, a new job.
Fortunately a recruiter connected me with a company in Connecticut and a new job starting January 2022. With rental cost being what they were early 2022, we decided to buy a house and in doing so dramatically downsize from our cozy life in the mid-west. By early March, we had relocated everything, including three dogs, but not including a sailboat to our new home in New England, comforted by the location feeling like a "responsible" stepping stone on our path to the dream.