Dear Senderos,

For today’s posting, I am going to reprint an article I wrote in 2013 titled, “Letter from a Long Lost Lover.”

I am doing so for two reasons.

The first is that I am a bit time-pressed due to the welcome fact that we are heading back to our home in La Estancia de Cafayate for the “season.” The “season” being when the residents flock south to enjoy a winter free of cold and full of the best things in life.

The second reason for republishing this particular article is because it contains philosophical musings about the paths our lives take, versus those we expect them to.

That particular theme rang loud early last week when I was told the EKG I had had during my annual physical revealed that some part of the wall of my heart had apparently stopped working properly. Further testing was needed to gauge the extent of the damage.

The medical term for this particular condition is “heart failure,” and while it doesn’t mean your heart has stopped (obviously), my subsequent research could find no favorable outcome.

Typically, the heart compensates the best it can, but over time it can’t keep up with its core function of pushing a sufficient amount of blood throughout the body, and you enter into a condition called “congestive heart failure.” After which you basically have three to five years to live, with the later years increasingly uncomfortable and then downright miserable.

So, that’s the starting point for this missive. At the end, I’ll circle back as I have just had a call from the doctor, and we’ll take it from there.
But first, this…

Letter from a Long-Lost Lover

My wife, an altogether incredible person whom, out of respect for her privacy, I don’t write about very often, jokes that I may have a mild case of Tourette’s syndrome because I tend to say and write pretty much whatever’s on my mind at the moment.

I may be about to prove the point.

You see, that my mind is wandering to less business-like pastures this morning is because the receipt yesterday of a letter from a long-lost lover.

We met in Chicago when I was first starting out in business, just barely out of my teens. I forget how we met or our first kiss, but I’ve never forgotten the time we shared or the influence our relationship had on my personal development and, by extension, my entire life.

Over the years I have often thought of Christine, and often wondered how life had treated her. Her letter expressed much the same sentiments.

Why our paths separated follows a script that will be familiar in that it stretches back to the beginning of humanity’s time on earth. Her mother, a well-known figure in the Chicago art scene and a fiercely independent and controlling woman, didn’t think I was the right man for her fair daughter.

Simply, even though we were really just barely out of childhood, the mother thought her daughter should only be involved with the marrying sort, a club she didn’t think I belonged to.

At the time, I remember being deeply surprised that Chris bent so easily to the will of her mother, but she did and so announced we must part ways.

Perhaps to prove her mother wrong, but mostly because I deeply cared for Chris, I proposed to her on one of the last nights we were together, but we had both had a couple of drinks and she didn’t take me seriously. While I can never know what would have happened if she had said yes, shortly thereafter we separated and were lost to each other in the crowd.

Our paths crossed again, albeit briefly, some years later when we found ourselves both living in the Los Angeles area. We had a nice dinner together, followed by a somewhat awkward moment as I was dropping her off, and then she stepped out of my life for the next few decades. That is, until her letter arrived a few days ago.

In her letter she told me that on that final night together, she had been trying to play it cool with me, but that at some point not much later she tried to get a hold of me to tell me that her feelings for me remained strong—and had never dampened. That listening to her mother was a mistake. But, her letter explained, when she called, my former brother-in-law answered and he coldly told her I was dating someone else and that she should let me go.

Besides being shocked that my brother-in-law had meddled in my affairs, I was sad to learn that Chris had thought I was somehow mad at her and didn’t want anything more to do with her, and so she got on with her life and I with mine.

While one can never recall the full details of something that occurred more than 30 years in the past, I have no doubt that the time Chris and I shared in Chicago was special and one of the most important relationships in my life, but I do have doubts that we could have ever rekindled the relationship once that chapter ended. And, as likely as not, if we had tried to appease her mother by getting married at such a young age, the marriage probably wouldn’t have lasted.

But Chris’s letter, bringing with it so many memories, made me further reflect on the chaotic nature of life. As much as we humans like to plan ahead and even dream of a glorious future—dreams that are especially vivid in our youth—the lives we ultimately live will be the result of a number of variables, maternal influences being just one, most of which are completely out of our control.

As an example of what I’m trying to communicate, I’ll point to the aspirations of many teens to get good grades, get into a good college, move on to a good job, marry the perfect mate, buy a nice house in a nice neighborhood with nice neighbors, have intelligent children, make money, and, in time, lay down the tools and spend the leisurely years of latter life in the bosom of a comfortable relationship, surrounded by legions of reasonably well-behaved progeny.

Even a casual glance around, however, reveals the American Dream—as the scenario I just described has been termed—as little more than a fantasy for most. Reflecting on the life experiences of as many friends and acquaintances as I can quickly dredge up provides a litany of bad and broken marriages, dread disease, business failures, persistent health problems or even unexpected death, substance abuse, job dissatisfaction, poverty, disappointments with children, frustration, stress, and more.

Of course, I can also point to examples of individuals who have enjoyed great success and happiness—and I think my friends actually skew more heavily in that direction than most—but the overall condition of humankind, I suspect, falls well short of youthful expectations.

Which brought me to the idea that the overarching challenge of life might not have to do so much with the frailties and failings of individuals, or even the vicissitudes of everyday life that can lay anyone low at any time, but rather with the expectations we develop in our youth.

Bear with my philosophizing just a bit longer and let me explain.

The way modern society is structured, the state encourages education in order to build certain core skills useful to the average worker bee. As parents who have been through the same indoctrination, we share this enthusiasm for such skill building but naturally want more, for the simple reason that we don’t want our children to be average. We want them to be exceptional, growing into the sort of adult we can talk proudly about to our peers, casually dropping news of citations won and rewards earned into conversation at every opportunity.

It is perfectly natural for a parent to want their child to do well—or, at the least, for them to avoid becoming a “problem” child, a troubled youth, or a dysfunctional adult. (So much so that over 6 million children are now receiving daily doses of drugs for ADD/ADHD—up from 500,000 in 1985. But that’s another story.)

And so parents, in conjunction with state-run schools and popular media, promote certain expectations from the earliest age. As a consequence, by the time the children have exited their most formative years, their expectations are largely hard wired—and thus they sally forth into life, only to quickly begin hitting the headwinds of reality.

Some kids barely make it into middle school before gritty reality begins wearing the shine off their early expectations. A bad teacher, a poor report card, a dysfunctional or over-controlling parent—and much more—might come into play.

Others might make it to college before they realize they’re not the sharpest knife in the drawer as their parents told them they were, but they soldier on because that’s what they expect to do, and are expected to do.

Following school—and for many, school ends with high school—the waves of reality rise high and the struggle to hold on to expectations becomes as hard as holding on to a surfboard in a surge of whitewater.

The strongest and the luckiest among us pull through the chop to calmer waters with expectations intact. But with each passing year, more and more people abandon their outsized expectations and settle in the smaller shore break of lesser aspirations. Some percentage, unfortunately, end up broken on the rocks.

Switching metaphors, in our youth, we envision the road ahead as being lit by the lanterns of our expectations. As a teen, we might visualize a higher degree, a good job, a good marriage, and all the trappings of success. But as we wander down the path of life, as often as not, the lanterns go out. The relationship you thought would be wonderful forever becomes a disaster, haunting your every waking moment. The job you wanted goes to someone else, and you end up an unappreciated cubicle jockey.

For many, the extinguishing of important expectations leaves them stumbling around in the dark, their way suddenly lost, their entire mental construct about their lives in ruins. At that point, many give up or turn to destructive behaviors to ease the pain, in turn leading to more pain.

Material success is no guarantee for happiness. In fact, some of the unhappiest people I have known were those who have exceeded all possible expectations for building wealth—only to find that money can’t, in fact, buy them love or even contentment. Having arrived, they find their penthouse suite empty, lonely, and unfulfilling. At that point they, too, can lose their way.

Wow, I can almost hear some of you dear readers thinking, he must be in a hell of a funk today.

But, actually, I’m not.

In fact, the message I’m trying to communicate is actually one of positivity and encouragement—or at least that’s how I mean it to be. You see, if you can ignore for a moment the social programming you received in your youth—no easy feat—I think it becomes possible to view life through a more realistic and, in my opinion, a much healthier lens.

For instance, instead of having any hard-wired expectations about how your life should unfold, start by accepting that the world we live in is chaotic in the extreme. And by chaotic, I mean changeable. What’s here today—the young love that Chris and I had, for instance—very likely will be gone tomorrow, regardless of how hard you try to hold on to it.

Therefore, rather than building a long-term future in your imagination that revolves around the relationship, enjoy the moment to the fullest, but in the knowledge that it can end at any time, for any reason.

That doesn’t mean it will, but to expect that it won’t means setting yourself up for disappointment if it does. (From a practical standpoint, anybody who gets married these days without a prenuptial agreement—a contract outlining each party’s responsibilities should the relationship end—is being naïve.)

Likewise, the job you think you want may not work out—or it might work out just fine. The investment you’ve made might blow up—or do really, really well. The neighborhood you buy a house in might deteriorate or appreciate, and the country you live in might not turn out to be the best or will be just fine.

I know that is stating the obvious—but then why is it that so many people get so heavily invested in their positive expectations that they are positively crushed when those expectations are disappointed?

Life is a crap shoot, and at any moment, the wrong die can come up—plan for it.

That said, one can’t just wander aimlessly through life. So how does one navigate in the absence of hard expectations? In my view, the key is to build core skills and adopt principles of such a strength and conviction that they’ll hold up under almost any conceivable scenario.

For instance, I think the well-equipped life traveler will want to be well read and widely informed about the world we live in. Ignorance may be bliss, but it’s also a ticket to a lifetime of working the counter down at the local Walmart.

To the extent that your reading leads you to becoming passionate about a profession that requires a higher degree, by all means, go for it. Just don’t do it for the future earnings potential or because it will please your parents, as that is setting yourself up for an empty life, versus one that is both fascinating and invigorating.

Learn about investing. After all, being able to intelligently deploy what capital you earn will serve you well in pretty much any economy, anywhere in the world.

Honesty seems to me a core principle that will make your life better no matter what, if for no other reason than that it will provide you with a good reputation... and people like to do business and interact with people of good, versus bad, reputation.

Pay attention to your health. It’s a challenging world out there, and you’ll need all the health and vigor you can muster—maybe even to help you recover from an accident or dread disease.

Being willing to put in a hard day’s work has always made sense to me. After all, people are far more attracted to hard workers than they are to the slothful.

Most of all, go where your passions lead you. As with higher education, doing something for the wrong reasons, or because it’s expected, will almost certainly lead to disappointment, which will only rarely happen when you do something you love, and you do it solely for the doing and not for some expected outcome.

I am sure there are other skills and principles you can add to that list, but if you were to approach life with just those, I think you’d be well prepared for pretty much whatever comes your way.

And with those core skills and principles in your quiver, you can then approach life in a way that I think is far more interesting and exciting than if you take a more conventional route.

Simply, view the world you inhabit as it actually is, an ever-changing, wildly fluid collection of new experiences waiting around each and every corner.

Sure, some of those experiences will be negative—in which case your refusal to be rigid in your expectations will leave you ready to duck, bounce, or just move on to whatever’s next. And many will be fulfilling and positive in the extreme, and you’ll be just as prepared to enjoy those experiences to the fullest.

The key is not to get so cemented in your expectations and your ways that you hunker down in a life not worth living and miss out on all the new adventures the world has to offer.

Eleanor Roosevelt, of all people, said that “Great minds discuss ideas; average minds discuss events; small minds discuss people.”

I wrote what I just wrote because I think that you and I, dear reader, are capable of discussing ideas beyond just where the price of gold is headed or the latest political shenanigans. I hope you concur.

In closing, I want to say how happy I was to receive the letter from my long-lost lover, as it evoked strong emotions despite the many years since last our paths crossed. As much as anything, I was happy to read she has lived a good life, as have I.

Back to the Present

Not so long ago, I wrote about the time that a former doctor of mine, after looking at my chest X-ray, broke into tears and told me through his sobs that I had advanced lung cancer.

His tears were because he was the emotional sort and because he had been my doctor for some years and felt guilty about having missed the cancer back when something could have been done about it.

For about four hours—until a follow-up X-ray at the hospital revealed that the problem wasn’t cancer but a collapsed lung—I was able to take a clear measure of my views on mortality. It was an eye-opening experience.

Well, I am happy to report that once again the inevitable is not imminent.

As the doctor just explained, the EKG said one thing—but the echocardiogram, a comprehensive study of the heart, showed that my heart was perfectly normal.

And so it is that this evening finds me seated on the back porch overlooking a beautiful Vermont sunset, reflecting on the past 10 days with the news hanging over my head that the sands of time were probably going to run out a lot sooner than I had expected.

Expectations encouraged, I might add, by the fact that my 90-year-old mother is still winning golf tournaments.

Naturally, when confronted with such news, one reflects on how to spend the time left if the follow-up test results were bad.

As mentioned, the prognosis for a damaged heart is a progressive downward spiral leaving me approximately three reasonably good years. So, I pondered, how would I spend those years?

Traveling the globe ticking items off a bucket list?

Hunkering down in Cafayate in the company of my family and friends while my health degrades?

Chasing about the world looking for a cure that doesn’t exist—or failing that, trying to get on a list for a heart transplant?

Or wait until my health began to seriously deteriorate, then climb on my horse Charming and ride off into the desert to face my end alone?
Some combination of the above?

At the end of the day, I came to a few conclusions.

  1. I wouldn’t want to be a burden on my family. I don’t suffer even the commonest of common colds quietly, so I’m pretty sure I’d make a terrible terminally ill patient.

  2. Based on the experience of being anchored to a tube in my chest in a hospital for five days—to repair the collapsed lung—I also know that I very definitely don’t want my last days to be spent in a hospital bed. Nothing could be more dehumanizing or degrading. Ergo the horse ride into the desert.

  3. I also realized that while the family finances are somewhat organized, if the news were bad, I would have to spend time tidying up and consolidating. I have known people who died with assets here, there, and everywhere, unnecessarily stretching the probate process out for years.

That’s about as deep as my contemplations ran. At the end of the day, I came to the conclusion that until you know for a fact that the inevitable is also imminent, it is impossible to make any firm plans.

As was the case with the faulty cancer diagnosis, I surprised myself by feeling at peace with the situation. I like to think that’s because there is nothing of any real consequence I have wanted to do in my life, but haven’t… if there were, I would have already done it.

So, no bucket list and no desire to start jumping out of planes.

The point of all this is a simple reminder that as much as we like to think otherwise, each of us is mortal, and none of us knows what tomorrow will bring.

In my case, I walked into a doctor’s office for a routine physical, which set into motion a celestial flip of the coin.

It came up heads, but it could have just as well been tails.

Winston Churchill once said, “Nothing is more exhilarating as to be shot at without result.”

Which I might rephrase as, “Nothing makes you appreciate your life more than a brush with your own mortality.”

And so it is that, sitting here on the porch, I am reinvigorated as I contemplate the trail ahead. I can have no real idea of where it will lead, but I am very much looking forward to finding out.

With that, I will sign off until next week or maybe the week after, depending on travel logistics.

Until next time, I hope you enjoy your own particular trail to the fullest because, really, you never know...

Speaking of trails, I mention La Estancia de Cafayate often because, frankly, I’m enamored of the place.

If you’d like to experience it for yourself, the very best time to visit is during one of the semi-annual Owners & Guests events. The next one will be held from October 28 through November 1.

Typically, about 50 of us get together for a week of fine dining, interesting conversations, wine tastings, golf, hikes, horseback riding, and generally enjoying each other’s company in the scenic wine country of Cafayate.

More information is available at If you do decide to join, let me know and I’ll be happy to buy the first bottle of wine!

Hasta próxima!


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