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5 Lessons From Will Smith’s Memoir

Growing up in South Jersey in the ’80s, just across the river from Philadelphia, I was an early fan of the local artists DJ Jazzy Jeff and The Fresh Prince (Jeff Townes and Will Smith, respectively).  

Memories of shopping at the Gallery Mall; buying mixtapes (actual cassettes) at Funk-O-Mart in Center City; hearing them and other pioneers of hip-hop on the local radio station Power 99 (way before streaming!); and even the strange coincidence of being classmates in a summer high school program with Will’s cousin, are still fresh in my mind.  

This was all before the sitcom actor, action movie star, Academy Award-nominated actor, and global icon Will Smith arrived. Could anyone have predicted that a hip-hop MC who signed his record deal while a senior in high school would go on to dominate Hollywood in the next decade and beyond – especially in the days before we had platforms like Instagram and YouTube?  

It’s because of those earliest memories rather than his fame and fortune that I’ve always seen Will Smith as a worthy role model from whose career path there is a great deal to learn. And it’s perhaps not surprising why he stands out so much for me, just as you may have someone in the public eye whose experiences always seem to resonate with you. 

Research has shown that we have “near-peers” with whom we notice commonalities in shared experiences, age, gender, ethnicity, or struggles.  

Perhaps the mental proximity in things like hometown memories, age, and the story of a black man (and in my case, brown) transcending social barriers toward global acceptance has made him always be a unique source of inspiration for me, relative to other successful people. 

So as you can imagine, I was excited to pick up his memoir, which came out on Tuesday, entitled Will. And on a personal level, it was gratifying and well-written (co-authored by the prolific Mark Manson who wrote the monumental bestseller “The Subtle Art of Not Giving a F***”).  

But I also read it from the lens of my work as an executive coach to highly successful people.  

As a coach, I’m constantly deconstructing what is working and not working for my clients to pursue goals effectively. I help them imagine operating as their “future self” and at their highest potential in current situations so they can creatively achieve the growth they desire but may not know how to attain.

And sometimes, helping them deconstruct the stories of their role models to learn from is a powerful method to explore innovative ways of approaching the challenges in front of them. 

On both fronts for me – as a Will Smith fan and as a coach analyzing his story for ideas – I was pleased to see one thing that he rarely has ever shown in his 30+ years of celebrity:  deep vulnerability.  

We all know the exceedingly funny, entertaining, and crowd-pleasing Will Smith. In later decades of his career, he also became famous not just for his movies but by sharing his philosophies on life, like having a killer work ethic and a “never-say-die” mindset. You can find a plethora of articles and video clips on these aspects of him. 

But in this memoir, he was refreshingly introspective and vulnerable, letting us in on not just what he accomplished and how but also why he did. And that the Will Smith attitude we all have come to know was in large part expertly crafted by him to avoid deep-seated pain and fear stemming from childhood. 

There are way too many thought-provoking passages in the 400+ pages memoir to discuss here, but here are five of my favorites, and after each, I’ve offered some of my coaching questions for you to consider relating to your life and work based on them. 

“The constant fear during my childhood honed my sensitivity to every detail in my environment.”

The primary source of Will’s fear was the militaristic style of his father, who he called Daddio.  

When he observed his father’s violence toward his mother but was frozen in fear of doing anything (while his younger brother, Harry, was unafraid to stand up to their father), Will developed the deep belief that he was “a coward.” 

He would spend the rest of his life and career haunted by this belief and triggered by people he believed were fearless and “hard” while he felt sensitive and scared.  

 These triggers could prompt jealousy (as in his self-comparison with Tupac Shakur, his wife’s childhood friend and deemed a poet and hero in the hip hop culture compared to Will’s more pop-centric style). 

The triggers would also lead him to desperately find safety in humor by cracking jokes (even if it meant going too far, as seen in him getting knocked unconscious by a classmate on his first day of high school).  

As he reflected on that first day at Overbrook High, he wrote, “I was always talking, always joking—I never shut up. I talked not because I had anything particularly important to say but because I was afraid. 

“It began to dawn on me that my overcompensation and fake bravado were really just another, more insidious, manifestation of the coward.”

 Your turn: Our upbringings define us in so many ways, often unexplored. And without reflection, we can find ourselves continuing to hide or push away the painful parts of our past through ineffective behaviors. What is something from your past that is worth some deeper introspection today? 

“My imagination is my gift, and when it merges with my work ethic, I can make money rain from the heavens.”

Will shares that his imagination ran so wild and rampant that his friends and family considered him an outright liar about most things. 

“I could make my mind believe anything,” he writes. “I was able to cultivate an almost delusional level of confidence. And while this somewhat skewed perception of myself would often end in ridicule or getting my ass kicked when I was young, on many occasions throughout my life, it served as a superpower.”

But he also credits his father for his superhuman work ethic, which is why his imagination could lead to pragmatic results. 

“My father tormented me. And he was also one of the greatest men I’ve ever known,” Will writes.  

In writing this book, he offers sympathy and understanding for the volatile man his father was while also honoring his mother for her quiet intelligence and emphasis on learning – someone who believed in only speaking “when it improves on silence.”  

As he shared, “these three ideas-discipline [from his father], education [from his mother] and love [from his grandmother] would fight for my attention for the rest of my life.”

Your turn: Creativity and execution need to go together, otherwise dreamers won’t get results, and doers won’t change anything. Where do you see yourself having a bias for one or the other, and when? How might you begin to increase their coexistence in your life? 

“If Harry was ‘fight,’ Ellen was ‘flight,’ and I became a pleaser.”

Amidst the stress in their household, Will shares that he and his younger siblings (twins Harry and Ellen) managed it differently and ultimately resented each other for that. 

In addition to fearing his father, Will felt even worse when compared to his younger brother and sister, considering he was the eldest yet couldn’t muster the courage to stand up to him like Harry or disappear like Ellen.  

Instead, during conflict, he chose a different lane, which was to be the one that would aim to please and keep everyone smiling no matter what.  

“I decided to be funny,” he writes.  

I often use the Hogan personality assessment with my clients, which helps people recognize how they show up under stress relative to others.  

The Hogan Development Survey looks at components around withdrawing from people versus becoming bolder and dominant when under pressure. And there is an element related to becoming “dutiful” or diligent”: you may become more of a people-pleaser or more of a rule-follower when stressed.  

When Will wrote about his family dynamics, he touched on the same components. But sadly, as a child, you don’t know that these are natural coping strategies and that it wasn’t his fault when he couldn’t appease his father. And without that objective perspective, you can spend your whole life just coping and self-loathing rather than being compassionate toward yourself and transcending the stress.

Your turn:  How do you typically operate under stress? Do you withdraw? Do you become emboldened? Or do you become a follower? Then consider, how is your current approach working for you? Would you like to try on a different response that better honors your needs?

“Boy, why you need three cars?” [Daddio] said. “You only got one ass.”

As Will became a bona fide music star, he started “acting out,” buying cars, motorcycles, and other toys to gratify his ego. His father, ever the practical man, questioned the point of all these purchases.  

For a time, when it came to rethinking whether these purchases were necessary, Will “dismissed that foolishness quickly” and continued on the hunt for “more money, more women, more Grammys.” 

But he became a different person, one who was angry, defensive, and sensitive to “anybody who even looked at me sideways.” He wrote that none of the toys and the Grammys could “begin to fill the holes inside of me.”

We all can find ourselves pursuing extrinsic and intrinsic success; we want the outer world to see us, and we also want to feel that we are enough inside. Buying stuff when you make it big isn’t a bad thing; it’s what most people would do at first. 

But throughout the book, Will always connects his behaviors – whether it’s talking too much, chasing girls, buying cars, or constantly seeking validation – back to his earliest fears. And upon deeper reflection, he recognizes that acting out had its time and place, and then he needed to evolve.  

He writes, 

“…the same angry, aggressive persona you cultivated as a child to protect yourself from bullies and predators will now destroy every relationship you have if you’re unwilling to let it go. 

“Things can be perfectly useful and absolutely necessary during certain periods of our lives. But a time will come when we must put them aside or die.”

Your turn:  One of the most important areas I coach leaders is letting go of what worked in the past to make room for your extraordinary potential. What do you need to let go of now, and what new, albeit scary, phase do you need to step into with courage?

“We gotta go against stereotypical roles. We need to make people forget that they’re watching a rapper. We gotta make them see a movie star.”

When I’m coaching my clients, I can tell when they are “playing small.” 

There is a hyper-focus on the things right in front of them rather than their true aspirations. They are stuck in reactive mode rather than proactively strategizing about how they want their future to look. 

And they will often act in a way that says, “who am I to be doing that?” 

When this happens, I hold a quiet space with them where they have full permission to dream big without judgment. We suspend all disbelief and begin to create and then strategize.  

Will didn’t seem to have that problem; he constantly was dreaming big.

He wrote, “I didn’t deserve to dream this big. But in my quietest moments, alone, there was a consistent yearning, an emotional compass that was always trained on the Hollywood sign. [I decided] I want to be the biggest movie star in the world.” 

In his book, Will goes into great detail about how his friend and manager, James Lassiter, set that dream into existence by reverse-engineering the process.  

Rather than working hard and hoping, they deeply analyzed what made movie stars different from other actors and what the top films of all time and the top box office earners had in common.  

He had a “clarity of mission” based on his big dream, and he set out to do everything following the model of success before him. 

Now it’s one thing to believe you can do anything and have the work ethic behind it. It’s quite another to get others to believe in you. So for a sitcom star like Will Smith to get into the movies, he not only had to learn to act on a cinematic level, but he had to shed the one-note image he had until then.  

He could have easily auditioned for any comedy movie and started his entry from TV to film at this point in his career. And he probably could have commanded a nice payday based on the success of The Fresh Prince of Bel-Air. But that would have perpetuated his current brand instead of disrupting perceptions and preparing the world for his reinvention.  

So on his manager’s suggestion, he took a supporting role in Six Degrees of Separation, the film adaptation of a play starring cinema veterans like Stockard Channing, Donald Sutherland, and Sir Ian McKellen.

It was entirely out of his comfort zone and led to some unpleasant lessons in trying Method acting, but this decision is the pivot that got him one step closer to his big dream of dominating Hollywood. 

Your Turn: What’s a big, crazy dream you could imagine if you had to? Never mind if it’s reasonable; there’s no harm in imagining. And if you were to start pursuing it, what’s the shift that needs to happen in yourself and how others perceive you? Is there anything that you can learn from those who have already achieved that dream? 


As I tell my coaching clients, “Knowing why you need to keep proving yourself will finally set you free from the cycle of having to.” Otherwise, the feeling of never being enough will haunt you forever. 

And being honest about your pain will also cement an even deeper connection with those that support you. It will keep you from alienating them by your “never show imperfections” approach.  

In reading Will, I believe Will Smith, as he has become older and wiser, distilled his “why” so beautifully for all of us to read because there was something more motivating him than to be “the best.”  

Recognizing that his drive was based on ambition and avoiding pain and fear, he seems to have found more peace in his journey. But in the process, he has also created a more profound relationship with the public, on a different plane than just Will the entertainer.  

And for me, it was his vulnerable, often heartbreaking, introspection that made this the powerful book that it is.

Nihar Chhaya is an executive coach to founders, CEOs, influencers and C-suite leaders at global companies. 

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