Unfulfilled Dreams Can Make Us Suffer Even If Our Dreams Were Impossible

I dreamed of being a “magnificent ruthless fellow” as did Newland Archer from The Age of Innocence

I’ve always wanted to be in a position where I could make decisions that would affect the course of history. When I was five, I declared my intention to become President.

When I was twelve, I’d play an Avalon Hill WW2 war game against myself and slip into the fantasy that I was the commander-in-chief of combatant nations deploying millions of men to fight each other.  The armies were represented by small cardboard squares, but to me they were real enough to have conversations with.

While playing that game, I made no moral distinctions. I commanded the armed forces of America, the British Commonwealth, the Soviets, and the Germans with an equal sense of ardent responsibility. In fact, I’d try to rig the game so that the Germans conquered the Soviets as proof that the brilliance of my strategy could lead to a different result than actual history. ¹

When it came time to apply to college, I decided I’d go to Princeton’s Woodrow Wilson School of International Relations, then join the State Department, and rise rapidly until I was in the Oval Office advising presidents on grand geopolitical strategy. By then I had recognized my shyness but I believed my superiority in academics and my accumulation of knowledge could carry me forward to anywhere I wanted to go.

Then Princeton rejected me. I wound up at Penn in the Wharton School for business, which I dismissed as a mere trade school, devalued by how easy I found it to be. I could skip all my classes, read the textbooks, ace the exams, and get “A’s.”

I graduated a year early and went to Wall Street, carrying with me the idea that someday I’d start my real career. Until then I’d make money.

Shadows of Regret

This post came together after I read a masterful and thought-provoking Substack essay by

Laurie Stone

called The Grandstand and the Arena. In her essay, Laurie speculates that she’s been living under the shadow of a many decades-old comment made by a “friend” who proclaimed that Laurie lived in the “Grandstand” while she, the friend, lived in the “Arena.”

There’s much to be gleaned from Laurie’s essay and her writing. I recommend subscribing.

What captured my attention was Laurie’s metaphor of the shadow. We can all recognize shadows of regret from our past, whether in the form of hurtful and defining comments you can’t forget, the loss of a first love, and, in my case, the shadow of unfulfilled ambitions.

Some shadows are permanent, unavoidable and can never be cast aside. They are tragic and nothing can be done. For example, the death of a youthful first love, so memorably and achingly described in James Joyce’s The Dead. (For more on The Dead, read the footnote at the bottom.² )

But some shadows are illusory because the regret they represent could never have been realized. And to carry the burden of an impossible shadow with you for life is a different sort of tragedy, arguably worse because it’s unnecessary and self-inflicted.

Newland and me: two wannabe “major dudes” ³

When I encountered Newland Archer, the main character in Edith Wharton’s The Age Of Innocence,⁴ I recognized in him parts of my youthful self. Newland is a young paragon of New York society in the 1870s. He’s wealthy, spends his days dabbling in the law and reading to satisfy his intellectual curiosity. He’s engaged to a female version of himself, a pretty, well connected society girl.

But then Newland falls hard in love with his fiancé’s exotic cousin Countess Olensaka. And his love is not only for this woman but for the possibilities of escape she represents. He believes his entire future turns on the question of whether he can ditch his proper wife and run away with the Countess as far as India and Japan if necessary.  

Like I did, Newland longs for a more meaningful existence, an adventure, a true life of the mind, away from the strictures of his world, where his future lies before him as a deep dark rut of law and books, books and law.

Where I differ from Newland is that in romance, I have no shadows. I got to marry my version of Newland’s Countess Olenska, and my marriage has been an extraordinary adventure in making a life together over the course of forty years.

(Soon after we were married, in 1986, my wife Debbie and I did flee Manhattan’s East Side for the then “bohemian” West Side; it wasn’t India or Japan, but it seemed like a big deal to us.)

As for Newland, his escape from NYC with the Countess is thwarted by his extended family. The Countess goes to live in Europe without him. Thirty years later, we see Newland, aged fifty-seven, sad and lonely as a tourist in Paris,

“he felt shy, old-fashioned, inadequate: a mere grey speck of a man compared with the ruthless magnificent fellow he had dreamed of being...”. (the bolding is mine)

When being a ruthless magnificent fellow is out of reach

I eventually came to realize that my youthful ambitions were fantastical because making them happen was diametrically opposed to my character traits and abilities.

In terms of ruthlessness, the thought of being responsible for any human suffering horrifies me. In the course of my finance career I had to fire people. And each firing was a torment to me. I hate the idea of anyone being angry or even displeased with me. I’d be a wreck if I had to make decisions about sending people into harm’s way.

As for magnificence and seeking a path to political prominence, I’m an introvert. The idea of a politician’s tight, relentless schedule of meetings and fundraisers is a nightmare to me. And my one experience with being inside a political administration taught me that I lack the patience to deal with bureaucracies.

In contrast, poor Newland––who is as real to me as most people I know––lived permanently under the immense shadow of a regret that he never realized was impossible for him to achieve.

He never understood that had he succeeded in escaping with Countess Olenska, it would have been a disaster. He never fully grasped that his appeal to the Countess was wrapped up in her admiration for his sense of duty and doing the right thing, and that by running away with her, he would have squandered that appeal.

As well, Newland never would have been comfortable or been able to tolerate violating the code of the New York Society that was so native to him. He would have been like Anna Karenina crushed either literally or spiritually underneath the wheels of some train.

My shadow sometimes returns and bumps into reality

“I was the shadow of the waxwing slain By the false azure of the windowpane;” (Nabokov, Pale Fire) ⁵

I’m not totally rid of my “false azure,” the idea that I’m capable of influencing issues of great scope. As much as I tell myself that my grand ambitions have always been at odds with my character, periodically my hopes and regrets still rise up. Something will happen to convince me that I possess exceptional problem solving and decision making skills, and that I should use them on a bigger stage. That I’m capable of bending history with my mind the way that mentalist Uri Geller was said to be able to bend spoons just by looking at them. ⁶

For example, I identified with Newland Archer’s hopes when he tried to find his life’s meaning in politics. Asked by the Governor to serve in the New York Assembly, Newland quickly determined he was ill-suited for politics. That hope and its quick departure happened to me too.

I’ll watch and re-watch the TV show The West Wing and think I could be one of those youthful advisors, preternaturally bright and well-spoken, guiding the president to make decisions of great import. But then with some regret, I'll realize that they’re half my age, have already put in their dues to gain their positions, and work at a pace that leaves no time for their families or frequent naps and tennis games.

As I grow older and have more time to think, the shadow of my youthful ambition seems to be coming back more frequently.

I can still dream that one day someone will knock on my door and give me a chance to use my self-perceived brilliance to change history.

You have to listen very attentively to hear the sound of a knock that never comes.

Newland Archer in Paris. looking at the home of his “lost” Countess. At fifty-seven, he looks old and defeated..

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Question for the comments: What are your shadows, and were they unavoidable, realistic misses, or impossible dreams?

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1. The game I loved was called (embarrassing to admit) Third Reich. The rules were impossibly complex for a twelve year old so I simplified and improvised. There were ships and planes and Lend-Lease convoys and management of each combatant’s economy––spend it all in one year on armed forces or save some resources to boost permanently your war-making capacity.

Once, I let my younger brother Samuel (seven years old) play the Soviet Union. When his Soviet troops were annihilated by the German army, I told him he was responsible for the deaths of millions. Sorry, Samuel!

2. A powerful literary example of the permanent shadow caused by the death of a first love takes place in James Joyce’s short story “The Dead.”

Middle-aged Gabriel Conroy comes to realize he will always be eclipsed by the shadow of Michael Furey, his wife Gretta’s childhood love. Michael rose from his sickbed to travel through a storm to see Gretta, and that ill-advised mission of love led to young Michael’s death at seventeen.

Most people, including me, recall the famous last paragraph of The Dead. But unless you read and recall what comes before it, you forsake some of the impact of those last perfect sentences.

Here is Gretta revealing her lost, dead love to Gabriel who had hoped for a romantic evening in their hotel room.

“Then the night before I left I was in my grandmother’s house in Nuns’ Island, packing up, and I heard gravel thrown up against the window. The window was so wet I couldn’t see so I ran downstairs as I was and slipped out the back into the garden and there was the poor fellow at the end of the garden, shivering.”

“And did you not tell him to go back?” asked Gabriel.

“I implored of him to go home at once and told him he would get his death in the rain. But he said he did not want to live. I can see his eyes as well as well! He was standing at the end of the wall where there was a tree.”

“And did he go home?” asked Gabriel.

“Yes, he went home. And when I was only a week in the convent he died and he was buried in Oughterard where his people came from. O, the day I heard that, that he was dead!”

She stopped, choking with sobs and, overcome by emotion, flung herself face downward on the bed, sobbing in the quilt. Gabriel held her hand for a moment longer, irresolutely, and then, shy of intruding on her grief, let it fall gently and walked quietly to the window.

And here’s the famous last paragraph because you can never read it too often.

A few light taps upon the pane made [Gabriel] turn to the window. It had begun to snow again. He watched sleepily the flakes, silver and dark, falling obliquely against the lamplight. The time had come for him to set out on his journey westward. Yes, the newspapers were right: snow was general all over Ireland. It was falling on every part of the dark central plain, on the treeless hills, falling softly upon the Bog of Allen and, farther westward, softly falling into the dark mutinous Shannon waves. It was falling, too, upon every part of the lonely churchyard on the hill where Michael Furey lay buried. It lay thickly drifted on the crooked crosses and headstones, on the spears of the little gate, on the barren thorns. His soul swooned slowly as he heard the snow falling faintly through the universe and faintly falling, like the descent of their last end, upon all the living and the dead.

3. Reference to Steely Dan song, Any Major Dude:

“Any major dude with half a heart surely will tell you my friend 
Any minor world that breaks apart falls together again.” 

4. I’ve been reading Age Of Innocence as part of a reading group led expertly by

haley larsen, phd

who writes the Substack Closely Reading. I recommend her reading groups and others like it. I tend to read much more deeply when I know Haley’s going to ask questions to which I’ll want to respond. And when I know I’ll be reading the answers and the opinions of other readers.

5. The opening lines of the fictional poet John Shade’s poem in Nabokov’s Pale Fire, a book consisting of that epic poem and the even longer footnotes by the fictional narrator Charles Kinbote.

6. Uri Geller per Wikipedia.