I’m the Guy Who Wrote “The Art of the Deal”

So what is it I've been seeking all these years?

Good morning fellow scribes, wordsmiths, storytellers, unpaid novelists, laid off journalists, untenured scholars, professional inventors and reinventors.

I come to you this morning as a rueful, remorseful and penitent—a product of my own multi-decade redemption and reinvention.  

I accepted this invitation because I believed that you, fellow inventors and reinventors, would understand, and empathize with the fateful choice I made 30 years ago.

I want to talk to you about what you came here this morning to hear me talk about. Beyond, and more than that, I want to talk about the relationship between our inner lives and our outer lives, between conscience and paying for private schools, and about how we make choices in our lives.

Above all, I want to talk about what it means to be a whole human being, for better and for worse, till death do us part.

These are the sorts of dilemmas that have preoccupied me for more than five decades. Among all the roles I have played in my life, the primary way I see myself is as a seeker.  

I’m the guy who organized a “sensitivity training” workshop for my high school classmates at the age of 16.

I’m the guy who wrote The Art of the Deal, and then followed up with a book called What Really Matters: Searching for Wisdom in America.    

I’m the person who launched a company at the age of 47 seeking to convince big companies to better meet the physical, emotional, mental and spiritual needs of their employees.

So what is it I’ve been seeking all these years?

The facile answer is happiness, wisdom, enlightenment, meaning … the pot of gold at the end of the rainbow … the secret sauce … the holy grail … But none of these fully capture what I I’ve craved most fervently.

What I’ve really sought is to feel valued and valuable.

Valued and valuable. This is what I believe all of us are seeking most fundamentally, throughout our lives, even if we don’t always know it … and even if we spend vast energy avoiding the deep and difficult work that makes it possible.

I grew up believing I could never be good enough. I felt I didn’t really deserve love or respect, from others or from myself. But oh how I longed for it …..

My journey was motivated by discontent—the pain of not feeling comfortable in my own skin or fully at home in the world.

I grew up with a mother who I came to realize much later was deeply troubled …. and a father who didn’t have the wherewithal to protect me, or my brother and sister from her. My father was a kind, gentle, but passive man who was as terrified by my mother as my siblings and I were.

At the same time—to complicate it all—my mother was amazingly effective in the world: a passionate social activist and a pioneering feminist who fought all her life to make the world a better and more equitable place, even as she remained a volatile, raging and searingly critical presence at home.

My mother was more like a traditional father—albeit a tyrannical father—and my father who was more like a traditional mother—albeit a mother who worked all the time and wasn’t around much.

It didn’t add up. I never felt safe or secure, nor did my siblings. The experience of safety and security is what makes everything else in life possible.

All children are helplessly dependent on their caregivers. To survive, we each learn to shape ourselves in whatever ways we must to win the love and protection of those we most depend on, no matter how inadequate their care may be. Our hunger for attachment is even more intense if the primary source of our comfort is also the source of our terror.

I spent a great deal of energy trying to survive my mother—to separate from her and find my own identity without losing her love. As it turned out, I couldn’t have both.

I can easily imagine some of you saying to yourselves “Well I’m sure glad that wasn’t me.”

But here’s the thing: it was you, to some degree or another, because all parents fall short of unconditionally loving for their children, and all children grow up feeling … to one extent or another … vulnerable, unsafe, and insecure.

This is part of what it means to be human, much as we don’t want to see it, or feel it, or take it on.

My own solution was to become an achiever.

My mother very much wanted me to be successful in the world, and to make a positive difference, both of which she had done. Achieving and contributing, I concluded, would allow me to be my own person, but also to please her. Her specific ambition was that I become a justice of the Supreme Court—and more specifically the Chief Justice. My mother set a fairly high bar.

By the time I began college at the University of Michigan—disappointed at having been turned down by Harvard and Yale—I had decided I wanted to be a journalist. I wanted to “comfort the afflicted and afflict the comfortable”—a phrase that’s often and inaccurately attributed to H.L. Mencken, and was probably coined by one of your fellow speechwriters who never got credit for it.

But pursuing this noble cause in journalism was never simple, because in addition to afflicting the comfortable, I also wanted to be comfortable myself, and famous, and admired.

I wanted to make a difference …. but not at too much sacrifice to myself—the self that felt so vulnerable and insecure.

My heroes were the New Journalists—people like Tom Wolfe and Gay Talese; David Halberstam and Joan Didion—who were all great reporters, but also wrote stylish novelistic nonfiction and were as much appreciated for their writing as they were for their journalism.

These journalists weren’t ink-stained wretches toiling away in obscurity. They were stars themselves, nearly as well known, well paid and admired as those they wrote about.

I wanted to be like them, which I imagined would make me feel better about myself. It turned out that no matter how much I achieved, I continued to feel I fell short.

I didn’t learn that lessons for many years. Instead, I just kept doubling down, pushing harder, hoping to pile up enough bylines and accolades that no one could doubt my value.

After college, I sought a job in New York City, because I had grown up there and because I believed it was the center of the universe. I got offers in other cities, but somehow nothing counted if it wasn’t in NYC.

I began by writing for a small, hip magazine called New Times, long since defunct. Two years later, I hit my first real crossroads, when an editor from the New York Post, who I had been pursuing since college, agreed to meet. These were the days when the Post was home to much admired writers like Nora Ephron, Pete Hamill, Frank Rich, and Anna Quindlen.

The editor and I ended up having too much to drink, and by the end of the evening he had offered me a job not as a reporter, but as a gossip columnist, replacing Leonard Lyons, a legend in the field who was retiring after 40 years on the beat.

I knew nothing about gossip, and it surely didn’t fit my self-image (nor my mother’s ambition for me).  On the other hand, taking on the assignment would mean having a column in a major New York City daily—with my picture at the top.

It was not the last time I would make an expedient choice and rationalize it away.

For the next four months, I wrote an ingenuous column about how, despite my earnest efforts, I couldn’t seem to track down much good gossip.

At the end of the fourth month, Rupert Murdoch bought the paper, and promptly announced in an interview that one example of what he disliked most about the Post was … my column.

How dare I apologize for being a gossip columnist?

Within a week, just ahead of being fired, I resigned and Murdoch launched the infamous Page 6.

I got hired by Ed Kosner, the editor of Newsweek, who I had met on the cocktail party circuit, while searching for gossip. I felt relieved. It was a more anonymous job, but also more respectable.

I wrote about the media, books and entertainment. I nearly always went into assignments idealizing my subjects, and I often came out disillusioned. My talented and celebrated subjects were often struggling mightily behind their appealing public personas. They didn’t seem have life figured out much better than I did. Three years after I wrote a cover story about John Belushi at the top of his game, he was dead from a drug overdose at the age of 33.

Over and over, I was learning that external achievement is largely unmoored from internal satisfaction.

After three years at Newsweek, impatient for more notice, and more visible success, I got hired by the New York Times. Despite the prestige, I felt like just one among hundreds of reporters. I loved being associated with the Times, but I wasn’t eager to spend my career there.

Four years later, when I got the opportunity to write long-form cover stories for New York Magazine, I jumped at the opportunity.  

It was several years into working for “New York” that I first encountered Donald Trump. At the age of 38, Trump had achieved local renown in New York by building a very successful hotel atop Grand Central Station on 42nd Street, and then a flashy condominium in a prized midtown location, which he modestly named Trump Tower.

In early 1985, I got wind of the fact that Trump had purchased an older apartment building overlooking New York’s Central Park South. It was another prize location, but in this case the tenants in the building were living under the protection of rent control and rent stabilization, and paid very little for their apartments. Trump’s plan was to get rid of them, and turn the building into a luxury condominium.

To help in the effort, he hired a company that specialized in what was known euphemistically as “tenant relocation.” In practical terms, that meant failing to replace burned out lights in hallways, and not fixing the elevators when they broke, so that the mostly elderly tenants were forced to walk up and down the stairs. It also meant refusing to do any kind of general repairs, including leaks, and even threatening to fill vacant apartments with homeless people and drug dealers.

All of this was designed to make life so miserable for the tenants that they felt no choice but to move out. Talk about an opportunity to comfort the afflicted and afflicting the comfortable. This was the perfect opportunity.

To make it even more appealing, Trump was failing miserably in his efforts to push tenants out.

They organized themselves to fight him, hired a savvy lawyer, and refused to leave. In the article, I described Trump’s efforts as a case study in “how not to vacate a building …. the story of a gang that couldn’t shoot straight … a fugue of failure …. a farce of fumbling and bumbling.”

The cover image in the magazine featured an illustration of Trump looking like a thug—red-faced, sweating and scowling. This was journalism I could feel proud of.

To my amazement, Trump loved the article, and especially the cover picture, and he wrote to tell me so. For Trump, any publicity was good publicity. In this case, he especially loved being portrayed as a tough guy. Almost immediately, he had the magazine cover framed, and put it up on the wall in his office.

Trump was like no human being I had ever met. Qualities that most people would do anything to keep secret, Trump embraced. He was also a reporter’s dream. Wherever he went, he was likely to say something outrageous.

Several months later, I went back to conduct the then famous Playboy interview with him. A few minutes into our conversation, he mentioned that he had just signed a deal with the publisher Random House to do a book.

“What’s it about?” I asked.

“It’s my autobiography,” he replied.

“You’re only 38,” I said, half-jokingly. “You really don’t have an autobiography yet.”

“Yea, I know,” he said, “but I’m getting paid a lot of money to do it.”

 “People are a lot more interested in the deals you’ve made than they are in your autobiography,” I said. “If I were you I’d call the book “The Art of the Deal.”

The title had just popped into my head. I’m pretty sure I got it from Joan Didion and that she had used the phrase to describe the real nature of art in Hollywood—deal making—but I’ve never been able to confirm that.

“I like that title,” Trump said without missing a beat. “Do you want to write the book?”

As much as it makes me cringe to say so today, I suspect I was hoping he would say that.

I already knew that Trump was a bad actor, from my previous article. I also knew that writing a book with him would very likely undermine my future credibility as a journalist and subject me to the legitimate charge of having sold out.

The term was virtually invented for what I was about to do.

On the other hand, my wife and I had two young children and a mortgage we were struggling to pay with the relatively modest salaries we earned as journalists. I was very worried about our financial situation—perhaps unduly so. 

Once again, I rationalized my choice.

Writing Trump’s book, I told myself, would give my family some financial security, and even potentially free me to do whatever book I wanted to write next. How bad could it be to write a book about a big-mouth real estate developer?

It wasn’t as if he was ever going to run for president. I pushed my concerns about the kind of man he was—and the kind of man I wanted to be—into the background.

My mother, for one, was appalled by my choice. She disdained any focus on making money, and she saw Trump as a vulgar loudmouth.

Although I didn’t realize it at the time, I now see that writing “The Art of the Deal” was the equivalent of putting my finger in her eye. In hindsight, I realize it was a slightly perverse declaration of independence from my mother. 

Having crossed that moral Rubicon, I focused on making my own good deal with Trump. Most writers for hire receive a flat fee or a relatively modest percentage of any royalties the book earns.

Trump and I haggled back and forth. Ultimately, he agreed to share 50 per cent of his $500,000 advance. My $250,000 share represented five times as much money as I had ever earned in a full year of work as a journalist.

He also agreed to share 50 per cent of any future royalties the book earned.

Once the contract was signed, I arranged to meet Trump on Saturday mornings at his penthouse apartment in Trump Tower. My plan was to interview him for two or three hours at a time, until I had gathered enough material to write the book.

I imagined it would take several dozen such meetings over the subsequent six months—and told him so.   

It didn’t take long to realize I was kidding myself. In our very first interview, Trump got impatient answering my questions in less than 10 minutes.

He was more than willing to provide sound bites to virtually any reporter who called his office, but it was nearly impossible to keep him focused on any single topic for more than a few minutes. He had a stunningly short attention span.

“This is so boring,” he would tell me, with irritation, a few minutes into any interview we did. “I don’t want to talk about what already happened. It’s the past. It’s over.”

If I managed to keep Trump answering questions for 20 minutes, I considered it a major victory. He was like a kindergartener who can’t sit still in a classroom.

In all the time I spent with him, I never saw a book on Trump’s desk. It later dawned on me that he had likely never read a book in his adult life.

Twenty years later, during his presidential campaign, he confirmed as much. Asked at one point to describe a favorite book, he named “All Quiet on the Western Front.”  How old were you when you read that one? 

After a half dozen frustrating interview sessions, it became clear I wasn’t going to get a book’s worth of material by asking Trump questions. Eventually, I decided to simply show up at his office in the mornings and listen in on his phone calls.

I don’t ever remember asking permission. It was clear to me that if Trump could have had his way, the whole world would have been listening in on his calls.

When I arrived each day around 9 am, he was nearly always on the phone. I picked up an extension eight feet away from him, and listened in on his conversations for the next several hours, and often all day long.

Beside reporters, Trump spoke mostly with lawyers, bankers and brokers for the deals he was doing. Many of these people became primary source material for the book. Over time, I went and interviewed each of them, in order to fill in the details Trump was incapable of providing.

It was during these conversations that I realized I couldn’t take anything he told me at face value.

What others told me about Trump’s deals often directly contradicted what Trump had told me. That made me uneasy, but I reminded myself that I was writing this book for hire. It wasn’t meant to be my version of events, nor an objective account. This was Trump’s story, and he was sticking to it.

More than any human being I have ever met, Donald Trump has the ability to convince himself that whatever he is saying at any given moment is true, or sort of true, or at least ought to be true. As we all now know, lying is second nature to him, just one more way to gain advantage.

Facts to Trump are whatever he deems them to be on any given day. When he is challenged, as he has demonstrated over and over, he doubles down—even if what he has just said is demonstrably false.

I’m convinced that Trump believes even his most preposterous lies, and that the more he repeats them, the more true they become to him.

When it came to The Art of the Deal, I wrestled with how to tell stories that I knew included inaccuracies.

Eventually, I came up with this sentence, aimed at covering all potential untruths: “People want to believe that something is the biggest and the greatest and the most spectacular. It’s called truthful hyperbole. It’s an innocent form of exaggeration and a very effective form of promotion.” 

Trump loved that explanation, preposterous as it is. After all, there is no such thing as truthful hyperbole. It’s a sleight of hand, a purposeful misdirection. In the end, truthful hyperbole is just a trumped-up word for lying.

What I did so effectively in The Art of the Deal, I’m ashamed to say, was use language to reshape Donald Trump’s bullying, cynicism and one-dimensionality into a voice that seemed boyish, ingenuous and brashly charming.  

In the end, I created a character far more winning than Trump actually is. Even as I was writing the book, I’d begun to think of him as a black hole. With nothing to sustain him inside, he looked entirely to the external world for nourishment.

No amount of money, success, praise or attention was ever enough. No matter how much he got, the solace it gave him very quickly leaked out.

What I didn’t fully recognize at the time was how much of Trump’s neediness and hunger for affirmation I share. By seeing these distasteful qualities in such an exaggerated version in him, I could feel more righteous about disowning them in myself.

 At the same time, I understood in some deep empathic way Trump’s hope that more money and fame and external success would eventually make him feel better—and serve as substitute for the safety, security and love that he never got in childhood.

And which I didn’t either.

“The ultimate motive for seeking extraordinary success, power, or fame,” writes the psychologist Sue Blogland, “is to make sure that our feared rejection, born in childhood, never happens.”

“We want to believe that if we ourselves could just secure enough recognition and approval from the outside world, if we could feel sufficiently admired, we would be healed and our self-esteem secured.

“But no matter how great the success, the original narcissistic wound remains unhealed.”

Bloland also happens to be the daughter of the revered psychoanalyst Erik Erikson. Her insights grew out of observing the vast gulf between her father’s enormous external success and his inner torment.

In Trump’s case, he has more access to the attention he requires than ever before …. but that’s the equivalent of saying a heroin addict has kicked his problem once he has free and continuous access to the drug.

Trump’s dilemma is that his insatiable need for external validation puts him forever at risk of feeling worthless.

Trump grew up with a very powerful and brutal father, and an overpowered, passive mother who was in no position to defend him. I understood that dynamic, even if the roles were reversed in my parents.  

To survive, Trump determined that he had to go to war with the world. It was a simple choice for him.

He either dominated or he submitted. He either created fear or he succumbed to fear—as his older alcoholic brother had.

Trump treated every encounter as a contest he had to win, because the only other option was to lose, which was the equivalent to him of obliteration.

From early in his life, he deduced that the best way to stay safe was to take no prisoners. So Trump stood up to his father. He dominated his siblings. He became a bully in his neighborhood. When his father dispatched him to military school, Trump managed to get elected head of the Corps of Cadets.

Each of us moves through early childhood with a narrow, self-centered worldview. That’s the nature of development. The difference for Trump is that his worldview never got much wider, or deeper, or longer. By his own declaration, he is essentially the same person today, at 70, that he was at 7.

Along the way, he failed to develop qualities of character that most human beings do in the course of growing up, to one extent or another—empathy, generosity, reflectiveness, the capacity to delay gratification, an appreciation of subtlety and nuance, and above all, a conscience—an inner sense of right and wrong.

Even at 70, his when own sense of self feels at risk, he will lash out at Carmen Cruz, the struggling mayor of San Juan, to lift himself up …. or disparage the service of a war hero like John McCain, or humiliate members of his own administration. And without a moment’s guilt.

Because Trump has never spent time expanding his emotional, intellectual and moral universe, his worldview has congealed. Through his narrow lens, what he sees is a jungle full of predators out to get him.   

Win or lose, dominate or submit—this perspective lies at the heart of Trump’s internal narrative—the story he tells himself about who he is. It informs every choice he makes, much as our own narratives do in our own lives, even when we’re not consciously aware of them.

Trump’s drug of choice, is attention—as it is for so many public figures—but we each have our own ways to anesthetize ourselves against the experience of emptiness, despair, loneliness and inadequacy.

None of us is free of these feelings—they’re an unalterable part of being human. All of us look for ways to keep our pain at bay, precisely because it’s so painful.

We rely on defenses like denial, rationalization, blame and projection … or we turn to drugs, or alcohol, or video games or the Internet … or we turn into workaholics, or relentless achievers, or we become caretakers while failing to take good care of ourselves.

But any addiction has a predictable pattern. The addict keeps chasing the high by upping the ante in an increasingly futile attempt to get the same effect.

When the Art of the Deal was finally published in 1987, it became an instant #1 bestseller. Over the next year, I earned more money than I had in the sum of my previous career as a journalist.  

I liked having more money. Who wouldn’t? But it didn’t make me feel much better. And feeling bad proved to be an unexpected gift.

The ultimate irony is that writing The Art of the Deal led me down the path that I believe saved my life.

I’m reasonably certain I’m only person alive who was led to the dharma by Donald Trump.

In many ways, the last 30 years of my work have been a direct reaction to the values and world view Trump represented.

In my next book, What Really Matters, I set out to write about people who had led more reflective lives and had more inspiring and idealistic goals beyond their own immediate self-interest.

The experience was inspiring in many ways, but life has a habit of confounding our expectations.

In the course of five years of interviewing and getting to know scores of psychologists, philosophers, scientists and mystics who had spent their own lives searching for meaning … what I discovered was complexity and contradiction.

I met people who were often stirring in their words, and skilled in their practices, but who could also devolve, like the rest of us, into more primitive behaviors under stress. Many of them remained nearly as blind to the contradiction between their walk and their talk.

Over time, I’ve come to believe that each of us has an infinite capacity for self-deception.

For all the work I have done to see through my own blind spots, I know they are still there, rising up when I’m feeling most threatened.  

Over most of the past two decades, I have run a company called The Energy Project. We focus on helping organizations to invest more in meeting the needs of their employees. Along the way, we’ve helped thousands of people to more skillfully manage their own energy—physical, emotional, mental and spiritual—so they can lead happier and more productive lives.

All or this has helped me to lead a happier and more productive life myself—in large part because I have found a purpose higher than my own self-interest.

At the same time, I’ve evolved a more nuanced, complex and forgiving perspective on the possible.

Rather than trying to explain it, I’m going to try to show it to you. I’d like you to take out a pen, and a piece of paper, or use you phone, if that’s the way you roll.    

Here’s the exercise. I’d like you to take a few moments to think of a few adjectives that describe who you are at your best.

How did that feel? You wouldn’t mind hanging out with that person would you? 

Ok, now I’d like you to spend a few moments thinking of adjectives that describe who you are at your worst. Take another few seconds to write those qualities down.

So unless you’ve experienced writer’s block, each of you should have the beginnings of two lists.

So here’s the $64,000 question: Which of these lists describe the real you?

Isn’t it pretty obvious that you are both? And that you move regularly along the spectrum between these two poles?  

Isn’t it also plain that these two lists, together, represent a more complete and truthful way of describing yourself?

And finally, isn’t it the case that when you are at your worst, that’s not all of who you are? Or who you are all of the time?

This insight was life changing for me. It freed me from a binary perspective that had burdened me all of my life.

For the first time, the fact that I wasn’t always my best didn’t mean I was bad.

The fact that I wasn’t always right didn’t make me always wrong.

It was more complicated that, and so is life.

We cannot change what we do not notice. This is what true development and growth are really all about: seeing more and excluding less. The more you see, the more you have the potential to influence, and the bigger the human being you can become. 

At times, I can still behave like a frightened, defensive child. I am also still the person who made a fateful decision at 33-years-old to write a book with a man named Donald Trump. The instincts which prompted that choice have not disappeared.

But I am also far more aware of my vulnerable and needy instincts, and I have much more capacity to manage them … to make conscious choices about how I behave in the world, and to make amends and repair when I fall short.

The pull to my worst qualities is less intense, less frequent and it lasts for shorter periods of time. Because I spend less time defending my value, I have far more energy available to create value, and more capacity to love and feel loved.

This is the life Donald Trump has never lived, and never will.

But you can. The choice about who you want to be is one of the very few that no one can ever take away from you. It begins with being conscious in every moment that you have a choice.

“Loving oneself is no easy matter,” the psychologist James Hillman has written, “because it means loving all of oneself, including the shadow where one is so inferior and so socially unacceptable.

“Thus the cure is a paradox requiring two incommensurables: the moral recognition that parts of me are burdensome and intolerable and must change, and the loving, laughing acceptance of them, which takes them exactly as they are, joyfully, forever. One both tries hard and lets go, judges harshly and joins gladly.”

Our current narrative about who we are—the assumptions we hold—need not hold us.

Our fate is not unalterably fixed. The stories we tell ourselves are not immutable facts.

We can rewrite our stories, we can behave better in any given moment, and things can always get better.

At the end of Tony Kushner’s Pulitzer-Prize winning “Angels in America” the character Prior reflects on the horrific wave of death caused by AIDS and the gay community’s challenge. What he says feels poignantly relevant to the challenges we face today, in the era of Trump.

“The world only spins forward,” Prior explains. “We will be citizens. The time has come.

“Bye bye now. You are fabulous creatures, each and every one. And I bless you. More life! The great work begins.”

You, too, are fabulous creatures, each and every one. So bless you. More life. The great work begins.

Hashtag: Resolve to evolve.

Leave a Reply

Download Whitepaper

Thank you for your interest. Please enter your email address to view the report.