Hatching the Plan, Part One: My Wake-Up Call

You might say that this adventure started a year and a half ago, when Hallie (my wife) and I were sitting in bed reading, and I said, seemingly out of the blue, “When I sail around the world, I’m going to focus on the sailing, and only stop in a few places, like Cape Town and somewhere in Australia.” To which she replied, “You’re not going to sail around the world. You’re getting too old for that.”

  Wow, did that ever get my attention! I’ve always thought that I might sail around the world; that it was an option that I might exercise. The idea that the option might be expiring soon was a wake-up call. And I knew she was right that I didn’t have much time left before my physical abilities would decline, and my internal drive wane, and it just wouldn’t seem worth it to take the big plunge. Little did Hallie know that her comment, made without looking up from her book, was changing the trajectory of our lives.

No Regrets 010
Hallie

At approximately the same time, a conversation about retirement was happening with my mens team (much more about that at some point, but for now: we are seven men who have met for an evening every other week for 30 years, to support each other to be the kind of man we each dream of being). I reported that I had achieved a financial goal that I had set 14 years earlier. My intention had been to retire when I reached this goal, but now I was comfortably enjoying working three days/week, with no end in sight. The team challenged me on this. “When are you going to retire?” “Why are you continuing to work if you’ve met your financial goal?” “What is your purpose at this point?”

I didn’t see anything wrong with continuing to enjoy my work, continuing to have an income, and besides – the dollar target that I had set 14 years prior didn’t look so big and “safe” as it did back then (even after adjusting for inflation). The threat of permanently shutting off the income spigot changed my perspective on finances. One of my teammates said, “I know when you’re going to retire. It will be when something shows up that pulls you away, rather than you choosing to get out.”

 This resonated. Something was brewing that would pull me away. But still I thought things would proceed in a logical sequence:

  1. I would finish building the small boat in my basement boat shop, that I had started building 20 years before and was 2/3 complete. Although I hadn’t worked on it much for many years, now that my work was only 3 days/week I would put more time into boatbuilding.
  2. Meanwhile I would shop around for the right boat for a circumnavigation, buy it in a couple years, and spend a couple years getting ready to go.
  3. I would retire perhaps at age 65 when Medicare would kick in, and go. Probably the voyage would only be about a year long, as I planned to spend my time sailing (going East below Cape of Good Hope and Cape Horn) rather than “seeing the world.”

As John Lennon wrote, “Life is what happens to you while you are busy making other plans.”

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