Chris Gardner Beyond the Pursuit of Happyness: The Work Begins

What comes to mind when you think of wealth? Dollar signs? A photoshoot-ready home in a highly-polished suburb? Frequent trips to exotic locations and five-star dining? Or maybe the symbol of wealth for you is a freshly-valeted Ferrari, with bright red paint you can see your reflection in, leather seats, and an exhaust mistaken for the turbo-charged thunder of a jet engine.

It was a red Ferrari that mesmerized a 27-year-old struggling salesman one day in the early 80s, in a parking lot outside of San Francisco General Hospital. As the salesman was walking by, the car pulled up to the curb. Stirred by what he saw, he decided to approach the car’s owner, who was dressed to impress in a tailor-fit suit.

Instinctually the salesman approached the man with two questions: “What do you do, and how do you do it?” Those two questions sparked a chain of events that led to the salesman’s rapid rise in fortune, a bestselling memoir, a Hollywood film about his life, millions in the bank, and his own Ferrari. Not any Ferrari. A Ferrari once owned by sporting legend Michael Jordan.

Before the wealth and success, though, the salesman spent a year homeless on the streets of San Francisco, with his toddler son, moving between homeless shelters, park benches, and public toilets. Does the story sound familiar? The movie is The Pursuit of Happyness. And the man behind the story is Chris Gardner.

Despite his rags to riches tale, money isn’t everything for Gardner. Years after the film’s conclusion, Gardner turned away from riches, and away the successful business he’d developed. After 30 years in the finance industry, a heartbreaking loss led him to take his own advice — to pursue his own version of happiness. And to inspire others to dream.

A Fatherly Bond

Will Smith has only starred in two biographies. In 2001 he played the legendary boxer Muhammad Ali. Five years later, in 2006, he was playing Chris Gardner. Coincidentally, these portrayals earned Smith his only two Oscar nominations, both for Best Actor, in 2002 and 2007. In an interview with AALBC, Smith explained his reasons for choosing the role:

“I saw the 20-20 piece [on ABC-TV ] on Chris' life, and the power of the story blew me away. There was a look in his eyes, a confidence, and a strength, after having traveled that journey. He personified the American Dream. It felt to me that the reason that America has been successful in this world is based on the idea that Gardner is possible.”

Part of the attraction to Gardner’s story was the American Dream, combined with his unwavering care for his son, his desire to never give up. It’s hard to imagine Smith acting opposite anyone other than his real-life son, Jayden. The pair’s natural love and care shines through the screen. But Smith had to fight for Jayden to be cast, due to concerns of nepotism by executives involved in the movie.

To compensate for the conflict of interest, Jayden, who was six-years-old at the time, had to audition nine times. When the studio asked for a 10th audition, the film’s director, Gabriele Muccino, put his foot down. He told producers he was “emotionally incapable” of making the film without Jayden in the role. It was a fight worthy of the character Smith was playing.

To understand the fatherly bond, you have to look back in time. Gardner’s upbringing was one of violence and uncertainty. Born in Milwaukee, Wisconsin, in 1954, he never knew his own father. He was raised in poverty by his mother, Bettye Jean, and his stepfather, who was physically abusive.

Making a vow to be the father he never had, he was committed to providing for his children and being present. His daughter Jacintha was born in 1985, after the events in the movie. Christopher Gardner Jr. was only two-years-old during the spell of homelessness.

Gardner, whose daughter had to convince him Smith was up to the task of portraying him by reminding him he played Ali, worked closely with the actor through the production and filming process. The pair enjoyed strong chemistry, which shows in Smith’s portrayal. Mirroring Gardner’s love for his son, Smith said:

“Jaden and I got to spend every single day, 10 or 12 hours a day, together, working on this film and it became clear that whatever you have to offer financially doesn't matter. Whatever situation you are in, it doesn't matter. You have to be there. You have to be with your child. To be able to spend that many hours a day together, our bond took off in a way that I never imagined.”

Although Gardner went on to earn his fortune — his current-day worth is estimated to be around $60 million — it was never his true motivation. His pursuit of happiness was something money couldn’t buy.

Ironically, it would be years until Gardner took his own advice and turned his back on the finance industry to follow his passion.

Pursuit of Happyness to Happily Ever After?

When capturing someone’s life story into a film lasting a few hours, what do you include? What do you leave out? Feel-good stories often end at a moment of triumph, celebration, or redemption. Stories can’t go on forever, they have to end. The credits have to roll, the audience has to return to their lives. In the Pursuit of Happyness, the happily ever after ending packages the uncertainty of life into a neat conclusion.

The immortalized story zooms in on a few years in Gardner’s life. Over two hours, we see his journey from struggling salesman, single father, homeless and broke, attempting to earn a job at a top stockbroker firm, Dean Witter Reynolds — an opportunity offered by a man in the red Ferrari, Jay Twistle (Brian Howe), who was a successful stockbroker.

Before his opportunity to change career, Gardner attempts to sell medical equipment, which he’d gambled his life savings on. Growing debt and pressure to provide for his family led to the breakdown of his marriage, and eventually, his wife leaves with his son. Gardner tells his wife to return him, which he does. That’s when his financial situation escalates.

Unable to pay for rent, he’s told to leave his apartment in a week’s time. The day before his internship interview, Gardner is arrested for unpaid parking fines and has to stay in prison overnight. He sprints from his cell to his interview, arriving in a vest and trainers, covered in paint from last-minute apartment renovations.

Yet he charms the panel and lands the internship, only to find out it's unpaid. Dedicated to making a better life for himself, Gardner agrees. He moves to a nearby motel with his son, where he is soon kicked out for unpaid rent, leaving him on the streets. The most poignant moment comes as he and Chris Jr. spend a night sleeping rough in a public toilet.

Through spells in soup kitchens and homeless shelters, Gardner keeps his homelessness secret from his colleagues, doing all he can to earn enough to impress enough to be offered a full-time role. Against all odds, Gardner makes it through his internship whilst struggling to look after his son and keep his life together.

As the film approaches the conclusion, the fateful day arrives. In an emotional scene, Gardner is called into the office and offered a full-time position. With tears in his eyes, he walks the streets in disbelief, picks up his son, and walks into the sunset, as the real-life Gardner walks by.

The uncertainty of life, packaged into a neat conclusion, and Gardner is set up for financial security and happiness. His first step was affording an apartment and a roof over his head, already a leap from sleeping in public toilets and homeless shelters. In 1987 Gardner founded his own firm, Gardner Rich. He became a multimillionaire. But this wasn’t happily ever after.

Life goes on, after moments of triumph, celebration, redemption. Events in Gardner’s life once the credits rolled would make for an equally-compelling sequel. His biggest challenge, greatest loss, and most heroic chapter was yet to come.

The ‘Y’ in happyness

Pursuit of Happyness is noticeable for its deliberate misspelling of the famous phrase from the United States Declaration of Independence. Gardner’s inspiration came from a daycare center he sent his son to, as shown in the film. But the meaning stretches back to a 1776 essay by a biracial man, Lemuel Haynes, who argued blacks and whites were created equal.

Gardner has added his own meaning, too. The Y is about “you” — finding your unique happiness, in whatever way that looks. With that comes the responsibility to work for it, to understand what you want, and make it happen, not to rely on others, or chance. Asked in 2009 if he was happy, Gardner responded:

“I am healthy. As a single parent, with a lot of help, I've raised two children that have become very special young people. And I'm doing work that reflects my values. That makes me happy. And you'll notice I did not mention movies or money. Money is the least significant aspect of wealth.”

Certain facts in the movie deviated from real life. The internship paid a salary of $1,000 per month, which he spent on daycare for Chris Jr. The man in the Ferrari was Bob Bridges, not Jay Twistle. He sold various medical equipment and didn’t invest his life’s savings. Most importantly, his onscreen wife, Linda (played by Thandiwe Newton) is a combination of two women: Sherry Dyson, Gardner’s ex-wife, who he was married to between 1977 and 1987, and Jackie Medina, the mother of his two children.

This creative retelling meant that another woman, Holly, wasn’t shown in the film. Yet she was the person Garnder calls “the love of my life.” And it was Holly who catalyzed his change of direction. “You can lose a house, get a new house. Lose a job, get a new job. But when you lose the person that you love more than life… that's irreplaceable,” Gardner told Goalcast in an exclusive interview.

The romance started unexpectedly, on what appeared to be a normal day. “I'm on the stationary bike, and suddenly the most incredibly beautiful woman I've ever seen in my life walked into the gym. She's got no makeup. She's drenched in sweat from head to toe,” he said. But the attraction was far beyond physical. “It wasn't what she looked like — it was what I saw and felt,” he added.

Overcome by a desire to get to know her, Gardner followed the same instinct and courage that encouraged him to ask the man in the red Ferrari. Whilst that question led to his ultimate fortune, Gardner’s question to Holly led to another kind of wealth. He approached her and asked her out. “She could have said no. She could have said, I'm in a relationship. She could have said, I'm not interested. I had to know. And I'm glad I did.”

In 2012, six years after the release of Pursuit of Happyness and 20 years after they met, Holly died at the age of 55. “I will never forget waking up one morning. Holly would always bring me a cup of coffee to bed. She said, ‘I have to tell you something. I'm losing my vision.’ And it wasn't the words but how she said them that made me sit up on the bed.” His fear was founded. Holly had an inoperable brain tumor.

After initial denial, Gardner faced up to another level of suffering and hardship. “It has given me a new perspective on what it means to struggle. I had overcome every obstacle achieved, every goal, slayed every dragon. I had done everything that I was supposed to do in that business, started at the absolute bottom, scratched, fought, crawled, and worked to the absolute top.”

“I could have continued to sit at that desk and chase some more stocks. Chase some more bonds. Chase some more deals… I could have done that, but when Holly was diagnosed, it changed everything.” Over the next four years, Gardner was Holly’s prime carer, which he calls an honor. Despite the struggle, the pair experienced moments of joy, love, and intimacy. It led to a profound change in his life.

Still working tirelessly at his successful company (his work ethic is symbolized by the fact he wears two watches), Holly’s nearness to death led to a re-prioritizing of values. “She kept asking me the same question,” Gardner told Goalcast. “‘Now that we can see how truly short life can be, what are you going to do with the rest of your life?’”

A Change of Direction For Chris Gardner

Before her first session of chemotherapy, Holly had a stroke and fell into a coma for months. One evening at the hospital, Gardner whispered words of reassurance in her ear. “I leaned down and I said to her ‘baby, if you want to let go, if you want to stop fighting, I'm okay, I'm gonna be okay,’”. After months of being motionless, Holly’s leg moved. Her foot caressed his arm. She died the next day.

There was no going back. Although highly successful and enjoying his work, at the deepest level, Gardner wasn’t fulfilled. He quit his job the day she died. “I had to start taking some of my own advice,” he said. “I had written about it for a very long time, that if you're doing something that you're not totally committed to, that you're not totally passionate about, you're compromising yourself every day.” Turning his back on bonds, Gardner chose a new mission — to help others in their own pursuit of happiness.

He started a new career as a motivational speaker and author, traveling all across the world for 200 days per year. Prior to the pandemic of 2020, Gardner was regularly speaking to crowds of thousands. “So many people around the world are now having their own pursuit of happiness moments and experiences,” he says. “Part of my journey right now is to empower others as they begin and continue to take these baby steps on the journey to their dreams.”

Since Pursuit of Happyness was released in 2006, Gardner has written two more books. In 2009 he released Start Where You Are, a book filled with life lessons in how to follow a similar path of moving from the impossible to the possible, aptly answering the two questions he asked all those years ago: “what do you do, and how can I do it?”

In 2021, Gardner released his third book, Permission to Dream, inspired by Holly’s death. In an attempt to answer the question, “what will you do with the time you have left?” Gardner shares the true fable of an adventure with his nine-year-old granddaughter, Brooke, and in turn how he worked on giving himself permission to dream.

In between the change of career and writing, Gardner never forgot his roots and his spell of homelessness. He helped fund a $50 million project for low-income housing and job opportunities in the very same place he spent time on the streets with his son. He regularly donates clothes and shoes, and spends time volunteering in homeless shelters.

This Part is Called: The Hero

All stories have to end, but you can’t help but feel Hollywood’s depiction of Gardner’s life ended prematurely. The credits roll, but Gardner didn’t stop being an inspiration. Hollywood got to see the Chris Gardner who could overcome all obstacles, to transform rags to riches. But if the chapter after the film’s events had its own title — from building his empire, caring for Holly, and choosing to change his life direction to help others — it would be “the hero.”

Chris Gardner might have been immortalized for his rags to riches story. But more than anything, Gardner epitomizes a winner’s mindset. A man pursuing purpose, not profit. Gardner faced more tragedy and turmoil after the “happily ever after” his story depicted. But despite trying times, his approach to life continues to be an inspiration. Gardner is a man of value and determination, two things money can’t buy.

Perhaps that’s a criticism of the movie — it captures the love he has for his son, but it emphasizes money, and success, as true wealth. Gardner sees money as the least important aspect of wealth, a perspective that only increased after Holly’s death. “I no longer connect net worth and self-worth,” he says. “What you do doesn’t determine who you are.”

Gardner’s life changed that day in the parking lot, in ways he couldn’t have imagined. All it took was the courage to ask a stranger two questions, to follow his instinct. Asking a question in the gym led to 20 years of love and companionship with his wife, Holly. What questions can you ask, and where will they lead you?

What opportunities are waiting for you? How can you make your own luck? How can you live a life of value, purpose, and the type of wealth that comes from within?

“You can make money, you can lose money. You can't make time. How much time you got left in your life? Don't nobody know,” Gardner says. A man humbled by the raw reality of life, and what he terms “spiritual genetics” passed on by his mother, Gardner oozes as much wisdom as he does charisma. “There is no exit ramp for happiness,” he reflects. “There's no exit ramp for peace, tranquility, beauty, all those things sometimes are on this road.”

In Permission to Dream, Gardner shares his idea of Atomic Time— the desire to make every minute meaningful. With time the most precious commodity, how do you choose to use it? Go after opportunities, don’t look for exit ramps, stay the course. But don’t forget that the most important part of the pursuit is to occasionally slow down, pause, reflect, and take in the scenery, enjoy atomic time.

“Sometimes,” Gardner says, “the beauty is the journey.”

Looking at Chris Gardner’s journey, it’s hard not to agree.