Creative Regret — What We Can Learn from “The Art of the Deal”

As the political news cycle churned on these last few weeks, Tony Schwartz was introduced to the world as a man haunted by a compromise he made with himself almost 30 years ago. Schwartz (who I should disclaim is a friend) describes his compromise and his regret in epic proportions, but they should feel familiar to anyone who earns a living off his or her creativity.

“I knew I was selling out. Literally, the term was invented to describe what I did,” Schwartz told The New Yorker of his decision to ghostwrite The Art of the Deal, a book that would define Donald Trump as an unrivaled negotiator and businessman.

Credit: ABC

For storytellers and creative people, here’s the scenario: A powerful client offers a high-challenge, high-reward assignment that immediately sets off alarm bells. You’re “putting lipstick on a pig” as Schwartz describes it. Afraid to say yes, but unwilling to say no, you twist the opportunity to something that seems benign enough by drawing some boundaries within the project you will not cross (though you often wind up doing so anyway). You focus on the financial upside. You convince yourself the project won’t have much impact. You proceed.

Flattered by Trump’s attention and lured in by a half of the advance and royalties which would eventually total in the millions, Schwartz signed on. As the ghostwriter, he came up with the book’s theme and then developed a mythical Trump character: a man who could do no wrong. It’s a character Schwartz now says is totally fabricated.

The book would sell more than a million copies before reality TV producer Mark Burnett read it and got inspired to create The Apprentice. The show, in turn, would become a real-life expression of Schwartz’s invented character, a character that convinced millions of the real estate mogul’s genius and ultimately convinced Trump himself to run for president.

When I met Schwartz a few years ago, The Art of the Deal was an amusing footnote of his past. The compromise seemed to have gone as planned. Yeah, he’d written a book he wasn’t proud of, but what had been the harm? His client was happy, and Schwartz had received enough royalties to launch a very successful company, The Energy Project, a company that teaches inclusion and compassion in the workplace. His company, unlike his book expresses his highest values. He’d moved on.

Since 1999, we’ve been building Free Range, which is a social change-focused brand and innovation studio. Values are at the heart of our brand. We live by them, but still, choices about where to direct our creativity aren’t always easy. When I first spoke with Schwartz, I remember thinking about a few occasions when the studio was presented projects that posed a similar risk. Like Schwartz, I’d been flattered and tempted by clients who seemed intriguing and sincere at first. Maybe even harmless. Some of these opportunities were financially tempting but obviously troubling, greenwashing projects or astroturf political campaigns. Other opportunities were more subtly problematic, like international development schemes with good intentions but that were ineffective with donor money and sometimes even negatively impacted the communities they were meant to serve.

There was a rare occasion or two, when I realized a partner might not be 100% genuine in their intentions or effectiveness where I convinced myself it was too late to stop work. By then, I’d created a list of reasons why it was ok to soldier on. And like Schwartz, the consequences of these decisions in the short-term would prove minor.

Of course, Schwartz’s life would unexpectedly be upended decades after the decision when Trump emerged as a serious national political figure and then the Republican nominee. His footnote suddenly became his headline. “I’ll carry this until the end of my life,” he told The New Yorker. “There’s no righting it.”

Though Trump supporters have made Schwartz out to be an opportunist and disloyal friend, I believe he is sincere in his regrets and his desire to atone for his lack of commitment to his own principles — principles to which he has since admirably devoted his life. Whatever his true motivations for speaking up now, these are Schwartz’s demons to wrestle with.

But the story carries a message for all of us. Creatives — writers, product designers, user experience designers, illustrators — we each carry our own demons, the projects we participate in and the clients we take on despite our inner knowing of how our creativity should be used.

Schwartz’s story offers us an important reminder that the things we create will often outlive us, rippling far beyond the desks upon which we create them.

The more talented and hardworking we are, the larger the ripples. We can never anticipate their consequences but we usually have no trouble evaluating in the moment we act whether we are acting in line with or in opposition to our best natures. Of course, there are times when feeding our families or keeping our business from going under make us choose the “devil over our higher side.” (Schwartz’s words). Sometimes those decisions have to be made. More often, however, if we are willing to look or work a bit harder, we have the power to choose something else.

Like Schwartz’s mastery of language, the creativity we each possess is a gift. It is likely the most powerful tool for impact we possess — more than the purchasing choices we make, the charities we support or the votes we cast. Thirty years ago, Schwartz misused his gift, but this year he’s given us one by sharing his story and reminding each of us of the creative power we have to craft (or undermine) the world we’d like to create.


Written by Jonah Sachs, Founder and Partner at Free Range. Jonah is an internationally recognized storyteller, author and entrepreneur. His book, “Winning the Story Wars,” shows how values-driven stories are not only revolutionizing marketing, but represent humanity’s greatest hope for the future.

At Free Range, we love creative challenges with brilliant partners. So chime in with questions, comments, and other ideas, because the only way we’re going to make this happen is when we do it together. Get in touch at freerange.com.