The Last Voyage

Dean Pagani
5 min readJun 1, 2023

Next month I will be board a schooner built in 1916 for a four day sail off the coast of Maine. It is something I have wanted to do for about 40 years and I’m just getting around to it now.

There is no easy answer to the question why it has taken so long, but one simple answer is a lack of urgency on my part. I have always known the opportunity was there and every other summer, or so, the thought would cross my mind and I’d think — very dismissively — not this year. In all honesty I have to say that in recent years I’ve forgotten about the possibility of the adventure altogether.

Then, a few weeks ago, while planning my summer I went on line to find out whether a schooner cruise was available and how much it would cost. I found out the typical cruise is for four days, including meals, you can work on board or not — it’s up to you — and the price is reasonable. Living in Connecticut I could drive up and drive back in a few hours each way. I signed up immediately.

And so it is that in my early sixties I will now do something I have wanted to do since I was in my early twenties.

Over the last decade I have been making these kinds of decisions more often than not. The decision to do not to wait. It’s because there seems to be less at risk, less chance of making a fatal error that will haunt me for the rest of my life, and even if it does haunt me for the rest of my life — how long are we really talking here? Another week? Another twenty to thirty years? I know now that even thirty years goes by very quickly. It took living this long to figure that out.

At my age, deciding to splurge on a trip, travel around the world, learn a new skill, get an advanced degree, or start a new business carries less weight. It’s not like making the same kind of decision when you first graduate from high school. In those early years every decision feels like a lifetime commitment. One wrong move and you are locked in forever. When you are younger you still believe in forever.

During the pandemic I met a woman on You Tube — and when I say I met her I mean she caught my attention and I follow her latest posts from time to time. I do not know her entire personal story, because she doesn’t share a lot of details, but it is obvious that at some point she realized she did not like the life she was living and decided to make a radical change. In her case, as is the case for many people who find themselves producing You Tube content, her new journey involves motorcycles.

I introduce her here, because she has a saying she is fond of sharing. It goes something like this; “You are born twice. The day you are born and the day you realize you will not live forever.” This saying might evolve from the quote attributed to Mark Twain that says, “The two most important days in your life are the day you are born and the day you find out why.”

I do not worry about death. I am lucky. I am healthy and I do not feel my age. I do not think about when I am going to stop working. I think about what I am going to do next. I will say again, I am lucky, but I do know that my luck can run out at any moment.

I sometimes mention this in conversation with friends of mine and they usually react the same way. “Don’t say that!” Don’t tempt fate is what they mean. If we don’t talk about the end it will never happen.

This article is not about death, it’s about life. My father was obsessed with death. He spent the last forty years of his life worrying about what the end would be like and which of his perceived enemies would have the nerve to show up at his funeral. In the end it didn’t matter because he died in an unconscious state following surgery and he chose not to have a funeral. He was 90 and had spent nearly half his life worrying about an end he didn’t get to see. As far as we know.

There are people who have the good fortune to know what they want from life early on. They make their path and never turn back. There are others who discover new paths along the way and don’t question what came before. I am not one of those people. I question everything and I have a memory like an elephant when it comes to key moments and key decisions in my life. I revisit them often and I analyze why I made certain decisions and how things would have turned out differently if I had gone in another direction. I have no regrets about my life decisions, but I can’t help wondering how things might have been different.

The additional perspective I have gained only recently is — that in general — very few of the decisions we think are big decisions really matter. There are very few bad decisions we can’t recover from, quickly, or at some point. The things we own, the money we have, the property of various types; none of it really belongs to us. We only have temporary access to it.

I do not believe or buy into the advice some people give that you should live life with reckless abandon, especially when it comes to financial decisions, but I have come to believe with greater clarity that there is almost always room for a come back. Because we don’t know how much time we have it is a mistake to think something we decide to do today will effect us forever. There is no such thing.

Here’s a story that is so good it doesn’t matter whether it’s true. It has been reported that in the final years of his life, Pablo Picasso worked harder than ever, because his mind was over-flowing with ideas, but he was fully aware he was running out of time. The lesson in the example is more important than the truth of the story. Don’t put off learning the lesson until the last half of your life. No matter your age, don’t let prudence keep you from taking a risk or responsibly pursuing a dream. Board the schooner as if it is your last voyage.

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