Earlier in my life I was a publishing mogul. Or maybe I should say that I spent exactly one afternoon thinking about being a publishing mogul.

For reasons I no longer remember, my college friends and I once went to look at an old printing press, one with movable type, a gorgeous turn-of-the-century antique. The person who was selling it kept the thing in his garage where it took up so much room that he had to leave his car outside. Next to the press were boxes of type and ink rollers, all seemingly in pristine condition, all waiting for young men like us with a dream.

We were 18 or 19, I think, and we had never printed anything. The four of us formed the editorial staff of our college newspaper, and all we knew was that we liked the look of our words on paper. And if our words looked beautiful on that cheap newsprint, then just imagine how beautiful they would look on expensive paper, with the type arranged just so. We would publish our own writing, yes, but we would find other writers too—maybe poets and even some novelists—who would write for us. Most writers would want to work with us, we thought, because of how beautiful the finished product would be.

On the way to examine the old printing press, my friends and I talked excitedly in the car about buying the thing as the start of a “publishing empire,” one that would somehow make all of us fabulously wealthy. Our not-very-promising little company, started with only an antique printing press, would one day challenge the giants of the industry.

Wealth, we earnestly said to each other, was not the goal, only one of the happy outcomes. What we really wanted, we said, was to make books, gorgeous books, collectors’ items—books, we began to realize, as we discussed the matter further, that no one would actually read. The books we imagined printing were instead going to be admired. Like the pioneering young men who had the vision to produce them!

Interestingly, not one of us grew up to be printers or publishers or anything close, and only one of us even stayed in the newspaper business after college. We didn’t buy the press that day, or even make an offer for it. I don’t remember that we ever talked about the idea again. We had lots of dreams at the time, and most of them lasted no more than an hour or two.

Becoming a publishing mogul wasn’t my first dream—and hardly my last. An even earlier dream was to become a professional baseball player. I loved the game and devoted hours and hours to playing and practicing it, but I gradually came to see that I wasn’t very good at it, not even good enough to make my high school team. Of all the dreams I had to let go of, that one was one of the most painful. I feel the pain of it now.

But then, as I have come to see, those early dreams are often not realistic, which is what can make them so charming. Early dreams are nearly always full of hope and imagination. Our imaginations, as much as anything, are what propel us into the future. We dream of a life before we live it. We think we can see it so clearly in our mind’s eye that we could describe it in detail, if anyone were to ask.

The life we get of course often doesn’t measure up to those early dreams, but what if we never dream?

*

I had a weekly tennis game for a few years with a physician, someone who had a settled and seemingly prosperous life in the U.S., with a nice house, a lovely wife, and some promising children.

So, I was surprised to hear him tell me one day, after a few sweaty sets, that he had once lived in Europe and played backgammon professionally. As a much younger man, he told me, he had spent months at a time in places like Monte Carlo and wagered what still seemed to him like unimaginable sums of money, in the end winning just enough to earn a modest living.

I never asked him why he quit, why he came back to the U.S. and decided to go to medical school. I had the sense, from the way he told the story, that he lived with a kind of wistfulness about this former life, that he may have given up on it too soon. If he had kept going, he seemed to say, he could have made a decent living at it. Others did, he told me, before he became quiet.

His story, which has stayed with me, made me think of my own lives not lived. I never lived in Europe as a young man, and I never played backgammon professionally, but I have had more than a few dreams of my own, roads not taken, lives not lived.

Sometimes I wonder what my life would have been like if I had followed through on one in particular. Not the dream of playing professional baseball. Or even the dream of starting a publishing business.

One early dream, which was surprisingly hard to let go of, was my dream of becoming a famous novelist. Before I was finished with high school, I had read all of Hemingway, and I could imagine myself, like Papa, living in Paris and writing words so startlingly beautiful that my readers would weep over them, as I did whenever I read his words.

What I never tried to imagine was the act of writing itself, the effort required to put words on a page. Instead, I would imagine the sleek and interesting women I would meet and the bars where we would have flirty conversations long into the night. I had not been to Paris at that point in my life, but the city was easy enough to imagine. I couldn’t wait to leave the uninteresting midwestern town where I grew up, and what better place to imagine living and working than Paris? Truthfully, I would have been happy at the time with any European capital, but when you dream you never think about second best.

The thing is, those dreams from the early years of our lives are nearly always a road not taken, something that could have happened, maybe, but for lots of reasons never did. Each of us has many roads we could have taken, people we could have married, jobs we might have enjoyed, places we could have lived. And any one of those roads would have led us in an entirely different direction from the choices we settled on.

*

My experience is that the number of roads that are open to us, even in our imaginations, narrows considerably as we get older.

At one point, for example, I thought about going to law school and described myself in college to anyone who asked—mostly my parents—as a pre-law student. I even took the LSAT one Saturday morning, as if to acknowledge the very real possibility of becoming a lawyer. But I must have known even then that the practice of law was not in my future. As it turned out, I hated the exam and didn’t care much for the looks of the people around me that day. I remember thinking, “Would I really want to work alongside any of these people?”

By saying no to the practice of law at that point in my life, however, I effectively closed the door on ever having a career in law. I suppose I could still go to law school today, maybe to prove a point, but who cares? And my chances of landing a seat on the Supreme Court? They were never good, but they’re near zero today. Some dreams, if we say no to them early on, remain forever out of our reach. No wonder then that there is often a sadness in older age when we remember what might have been.

*

I read somewhere that my generation was the first to be allowed to dream about the future. The exact words, as I recall, were: “Unled lives are largely a modern preoccupation.” In previous generations you lived pretty much as your parents had, sometimes in the same house, nearly always in the same town or village. That’s what my parents did.

I remember some pressure, when I was old enough to go to college, to stay close to home. The thought of moving away seemed to my parents to be an act of rebellion or maybe a criticism of the choices they had made. “What’s wrong with where you grew up?” they seemed to say, though they never used those exact words. My father came home from World War II and never had the desire to leave home again. It’s not that he wasn’t curious; it’s that he thought the world as he knew it was enough.

Usually there’s nothing “wrong” with where we grow up, except that at a certain age—for people of my generation, apparently—we begin to think about other possibilities, ones we would read about or see in movies or simply imagine on our own. Mine wasn’t the first generation to be curious; mine was the first that didn’t have to work on the farm or go into the family business or take care of aging parents. My generation was free to imagine a different life.

My father, as I remember it, never wanted any of his children to go into advertising, which had been his work since he returned from the Pacific. He always talked about it as though there was something distasteful about it, as if his children should make better choices with their lives. And that seems to have been all the permission I needed to leave my hometown, to explore some of the world, and to figure out what my choices were.

*

Not all of this was easy—at least it hasn’t been easy for me. If I’m making all the dreaming I did as a young man sound adventurous, well, it was—at times—but it could also be unimaginably hard. I remember falling into a depression more than once in my life, and each time it was because I had wanted something, or thought I did, and then I didn’t get it.

For me dreaming has had its downsides. Sometimes what we dream about, what we think we want more than anything in the world, turns out to be the worst possible thing. Dreaming, and then acting on those dreams, can often involve some hard lessons.

I was once offered a job as director of graduate studies at a small school in the Midwest. I was thrilled to be interviewed, and the people I met seemed interesting. I was flattered of course by their interest in me, and as I walked around the campus, I could imagine myself there. The academic world was one I had never explored, and for that reason alone I was interested.

And then, on the ride back to the airport, the person who was my host during my brief visit said to me, in a confidential tone, “things at the school are not as they seem.” He wouldn’t say more and asked me not to tell anyone what he had said. I wondered briefly if it was my host who didn’t want me to come, if he might have been interested in the job. But I thought about his words at the airport and then again in the air as I flew home. By the time I got home I decided to call the school and say that, regrettably, I could not accept the job.

A few weeks later I learned that the president of the school had resigned, after a small scandal, and I realized then that someone I didn’t know (and who didn’t know me) had done me a favor, had helped me to avoid a bad decision. The position I had been offered was eliminated soon after the scandal broke, and I remember feeling relief, mixed with sadness that I had missed out on something. I never again had the opportunity to work in an academic setting. It was another of those lives which was briefly within my grasp and then not lived.

*

I am a spiritual person, but I never liked hearing someone say, especially in the wake of a disappointment, “Well, the Lord must have other plans for you.” I never found any comfort in those words, and I don’t believe them. If “the Lord” had other plans for me, why did he dangle something in front of me that at the time seemed just right?

As a matter of fact, I believe that “the Lord” does have plans for us, but they seldom involve a particular job or a fascinating city or even a certain romantic partner. I doubt that there is just one special person in the whole world who is destined to be my soulmate, as part of “the Lord’s” plan for me, though I sometimes feel as though I am in a minority about that. What “the Lord” really has in mind for us, I believe, is what the Hebrew Bible calls “a future and a hope.” What we make of that future is the most important work we do.

*

I was never a big fan of the Robert Frost poem about the road not taken. When English teachers over the years implied that Frost was encouraging the reader to take “the road less traveled,” I was never convinced. I always thought the meaning of the poem was more ambiguous than that, and deeply frustrating for that reason, but I never dared to raise my hand in class and say so. I thought then, just as I think now, that either road in the poem would have been just fine. What’s important is how we travel it.

I forget now who said it, but I agree with the person who said, "I regret less the road not taken than my all-fired hurry along the road I took." That’s exactly how I feel. Whatever road I chose, I tried my best to enjoy it, but too often I was in an “all-fired hurry” to travel it.

That’s another of my regrets, now that I think about it. I regret having been in such a hurry all the time, treating new opportunities like competitions, wanting to win a medal at the end. Much later in life I have come to see that there will be no medal at the end. And there are no winners, even though some people like to think they are, which I suppose is fine for them. The best part of taking one road over another is enjoying it while we are on it.

Some people, I’ve noticed, like to add YOLO to a text or email about some new adventure in their lives, as though that’s the main reason to try something new. It’s true enough that “you only live once,” but is it important to experience every dream in a single lifetime?

To be honest, I lived a lot of my life with a YOLO attitude, and as a result I was able to see and do a great deal. I eventually did live in Europe, for example, though not in Paris and not as a novelist. Zürich, Switzerland, as it turned out, was quite a nice place to live, and I was able to live and work there for several years. I even learned to speak German while I was there which, believe me, is not easy to do later in life, but I passed the competency test and felt proud of myself for doing it, even though no one will ever mistake me for a native speaker. While living there, I also managed to see much of the rest of the continent, behind the wheel of a 20-year-old Volvo station wagon.

I once climbed Mt. Sinai at night with my nephew, starting at the base of the mountain just after midnight and arriving at the top in time to see the sun rise over the Gulf of Aqaba. I hiked to Machu Picchu one summer and another time, after I retired, walked 500 miles across northern Spain, a pilgrimage called the Camino de Santiago that hundreds of thousands of people have walked since the ninth century. I’ve led mission trips to build houses and dig wells in places like the Philippines, the Dominican Republic, Haiti, South Africa, Peru, and the Galilee region of Israel. I loved doing this and count all of it as living out a dream, but I never felt compelled to say, “Hey, you only live once!”

I still can’t hit a baseball, and I never learned to dance. I can’t paint or sing or do much in the kitchen. I did go to Iceland one time but due to a severe winter storm never got to see the northern lights or even a single whale.

I have never been to China or traveled much in Asia, unless you count a brief stopover in Japan on my way to the Philippines. I once looked into a trek to the base camp at Mount Everest, but my plans were upended due to a global pandemic, which was a deep disappointment. I don’t know if a man my age should be hiking in the Himalayas, so I may never get there.

I once took a ferry from Cape Town to Robben Island and saw the prison cell where Nelson Mandela spent 18 of the 27 years he was incarcerated. I realized as I stood there that Mandela missed out on a lot of his dreams, probably most of them, a realization that has been for me a good reminder whenever I feel regret. He kept a dream alive for his country, though, and in the end that made for an extraordinary life.

*

I must admit that I never dreamed about becoming either a husband or a father, never gave any of that much of a thought. I’m not sure many men do. I kissed a pretty girl one time, though, and then not long after she agreed to marry me. Together we had two remarkable daughters. I was present for their births, piano recitals, graduations, weddings, and most of their other milestones in life. I still feel a sense of wonder whenever I see them. I could cry right now just thinking about them.

Those experiences, getting married and becoming a father, have turned out to be better than any of my dreams, which surprises me. It was not what I expected. It’s possible that the best lives we live aren’t the ones we spent any time dreaming about.

Someone should explain how that works. I wish I had known.