When “If” Became “When”

Each year I write a letter to enclose in our Christmas cards. It encapsulates the highlights of our family’s year just ended. I’m told it’s pretty good. In fact, I joke (somewhat seriously) that all the positive feedback I’ve received is what convinced me that I should try writing a novel.

For the last half dozen years, each letter has concluded with a brief note about how we are considering downsizing our lives, moving aboard a sailboat, retiring early and heading over the horizon to see what the world has to offer.

About two years ago, I typed up some ideas on how we might actually make that happen and sent it to Rhonda. In typical two-career-couple fashion, we do much of our communicating during the day via email from our respective offices. I outlined a possible timeline in an attachment and sent it to her.  It was the first time we had something on paper that stepped through the process of fixing up our house, putting it on the market, selling our current boat, shopping for a larger one, moving aboard, retiring, and taking off.  I included a proposed itinerary of possible destinations for the first three years of our journey.

Putting something on paper gives it substance. It stops being an idle thought and starts becoming a strategy. But through it all, we’ve always said if, not when we go. We always hedged, because in our hearts I’m not sure we truly believed it would happen. Seeing it on paper was both thrilling and frightening, but it still felt more like wouldn’t it be nice than this could be real.

But yesterday, things just got very real. A big piece of the dream fell into place. A huge piece— probably the biggest piece necessary.

Our new boat arrived. The magic carpet that will transport us to all those places that have only been a wish and a dream.

And suddenly, I realize it’s no longer if. We’re on our way. The pieces are falling into place. The plan is becoming action. There’s momentum now.

It’s frightening. Change this large is hard. But they say if your dreams don’t frighten you, they’re not big enough. And so I’m excited about our future.

Because yesterday, I believe if finally became when.

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One thought on “When “If” Became “When”

  1. anniedike

    Robert … truly touching words. “When” needs to always be as soon as you can. And while the “can” component will always frighten you, if it excites you at the same time then you’re there. You can. Find a way. Congratulations to you and Rhonda both. This is a BIG step.


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