Escaping the Trap of People-Pleasing


“The world can only see us as we see ourselves.”

― David R. Hawkins

 

 

The year was 1983, and the “Godfather of Soul”, James Brown, was playing an electrifying show in Los Angeles, California.

Just when the show couldn’t get any more exciting, Brown spotted Michael Jackson in the crowd, iconically dressed in a Sgt. Pepper-style blue jacket and aviator sunglasses. Brown promptly invited him onstage, sending the audience into a manic frenzy.

Jackson took the mic and belted out a few lines as Brown’s band played in the background. Then, with effortless grace, he dazzled the audience with his signature dance moves. Like a proud father, Brown looked on in awe, as the young star he had so profoundly influenced earned a standing ovation from the audience.

Before Jackson stepped off from the spotlight, he could be seen whispering to Brown’s ear. Jackson reportedly told Brown, “Call Prince up. I dare him to follow me.”

Brown responded, “Who?”

 


 

At that point in time, Michael Jackson was indisputably the biggest pop star in the world. He had just released his masterpiece, Thriller, a month earlier. And on top of that, he had already been in the limelight for nearly his entire life, having been the singer of The Jackson Five since childhood.

Conversely, Prince had to built his career from scratch. He didn’t have the advantage of a Motown machine or childhood fame. He had to fight his way through, relentlessly proving himself with each album.

By that year, Prince was an emerging star, though he was still chasing the same level of dominance that Michael Jackson had already achieved. It would take Prince another year until his album Purple Rain would make him a legend.

Still, it was clear that there was an intense sense of competition brewing between the two artists.

And it just so happened that they were at the same show that night, tuning in to the same performer that they both grew up idolizing.

“Give (Michael) a big round of applause because he just insisted that I introduce Prince!” Brown announced to the audience.

Eager to gain the upper hand in the situation, Prince attempted to make a dramatic entrance…by piggybacking his bodyguard. Given his short stature, it only made him look even smaller. Things quickly got a lot cringier, as Prince obviously tried too hard to one-up his rival.

He grabbed a guitar from Brown’s band, but barely played anything of note, because it wasn’t tuned to his preference. Not knowing what else to do, he stripped off his shirt, attempted a few awkward dance moves, and made strange shrieking sounds as he gyrated.

Most embarrassingly, he then tried to grab a prop street lamp, which wobbled and caused him to fall off the stage.

It was one of the most humiliating experiences that Prince had ever endured — and a perfect example of how chasing approval can often backfire spectacularly.

 


 

“Maybe he didn’t realize people loved him for the person he is.”

— Karen Krattinger,
Former General Manager of Prince’s PRN Productions

 

A common theme throughout Prince’s life was his obsessive desire for control, particularly of how other people saw him. He wanted — no, he needed others to see him as the perfect, idealized public image that he had finely crafted for himself.

On a positive note, this made him insanely competitive as an artist, leading him to create a radically unique musical style. It prompted critics to create new terms, such as “funk rock”, “dance rock”, or the “Minneapolis Sound”, to describe his music.

This also led him to become one of the most prolific artists in music history. In fact, what contributed to his feuds with his record labels was that he was too productive. He would publish at least once a year, because by the time he put out new music, he was already bored with it and wanted to work on something entirely new.

As his home studio engineer and technician Susan Rogers said of him, “His discipline is one of the greatest assets. He’s always aware of how much talent there is out there and how good he has to be to be competitive.”

But on a more negative end, Prince was just as hard on himself as he was on others. His crew remembered rehearsals and recording sessions that stretched non-stop for over two days, and they didn’t get to go home at all. Needless to say, most people didn’t last very long in working with him.

As Rogers remarked, “You were exhausted, because this was a guy who’d work for 24 hours straight, then sleep for four hours, then work for another 24 hours…We worked so many Christmas Eves and New Year’s Days. It was compulsion, it was ambition, but it also filled a vacancy in his life.”

Perhaps most tragically, Prince was never at peace with himself. He constantly needed validation from others to prove his worth. His desperate attempts to control his image ultimately left him unfulfilled, and the more he sought approval, the more elusive it became.

There was an occasion where, out of his need to control his image, he attempted to create a sanitized documentary about himself, which was never released. He arranged interviews with other musical icons, like Eric Clapton, Randy Newman, and Miles Davis, to ask what they thought of him.

But instead of only getting their praises, Prince also got their criticism — which, by the way, is an entirely normal and healthy aspect of receiving feedback. Many of the interviewees commented on Prince’s self-indulgence and need for control; comments which he couldn’t stomach.

And towards the end of his life, Prince was compulsively scrolling through Prince.org, an online forum for his hardcore fans. He needed to know whether people thought he had lost his edge now that he was older.

Quite poetically, out of his never-ending obsession for such control, Prince passed away in 2016 due to his addiction to painkillers. Even in his failing health, he was still compelled to deliver as the great showman he had portrayed himself to be. He never wanted the world to see himself for he was — that he was just another human being. 

As Jill Jones, an actress and musician who closely worked with Prince said, “At his core, he was a consummate people-pleaser, trapped in the expectation to remain an enigma, always surprising, always beyond reach. The tragedy lies in the fact that so many refuse to acknowledge the truth of who he really was.

“He understood this better than anyone. He knew that revealing his true self — stripped of the carefully crafted persona — would lead to rejection. And, in a way, he was right.”

In a sad yet beautiful way, even his death seemed like a polished farewell performance. Echoing his own songs — Let’s Go Crazy and Sometimes It Snows in April — he passed away in an elevator in the month of April.

And soon after, snow fell.

 


 

“If you’re a control freak like him, you’re just trying to control your environment so you won’t get hurt. If you’ve been hurt as a child, you throw up all kinds of protections.”

— Owen Husney, 
Prince’s first manager

 

All of us have crippling insecurities, no matter who we are. And more often than not, these insecurities are deeply rooted in our upbringing. 

For Prince, his self-obsession could be traced back go a childhood where love often felt conditional, and expectations were impossibly high. 

His father was a jazz musician whose approval he deeply craved. As a child, he would sit outside his father’s rehearsals, absorbing the music and yearning for connection. 

While his father encouraged his musical talent, he was also strict and emotionally distant. After Prince’s parents divorced when he was 10 years old, his father left home, creating a gaping void that Prince would spend his life trying to fill.

Prince’s troubled upbringing played a crucial role in shaping his relentless ambition, as well as his crippling insecurities. His mother, forced to work three jobs, was often absent. His stepfather was abusive, and in one particularly traumatic experience, Prince was locked in a bedroom for six weeks with nothing but a bed and a piano. 

But his insecurities didn’t just stem from his home life — they were reinforced by the world around him. As a Black kid who was also short in stature, he was often bullied. He stood out, but not in the way he wanted. 

Teased for his size, and his race, he learned early on that he had to fight for respect. Music became his weapon, his way of commanding attention on his own terms. 

“Personally, I think a lot of his background feeds into his life. The divorce — a lot of things hurt Prince,” said Susan Rogers. That early hunger for validation followed him into adulthood, shaping his relentless ambition but also his deepest anxieties.

He wasn’t just competing with others. He was fighting against the fear that he would never be enough. 

Many of us can relate to that feeling — that desperate need to be seen in a certain light, to prove our worth, and really, to just be loved. Because of this, we contort ourselves to fit other people’s expectations, and we exhaust ourselves by chasing an ever-moving target of approval.

But people-pleasing, as you might already well know, is a trap. The more we seek validation, the more it eludes us. The world becomes a mirror reflecting back our own insecurities, and confirming our deepest fears. 

So, how do we escape this cycle? How do we stop defining ourselves through the eyes of others?

One life-changing thing I’ve learned over the years is that no one gives a fuck about us as much as we think they do. 

In psychology, this is called the “spotlight effect”. We’re often led to believe (by ourselves) that people are scrutinizing our every move, our every stutter, our every fumble. But the reality is, most people too busy worrying about their own insecurities and what other people are thinking of them.

Once we realize this, we’re free to be ourselves. 

Nevertheless, like anybody else, I wrestle with this all the time. I do catch myself idealizing and planning my boring day-to-day life like it’s a performance — what would people think if I didn’t buy that new shirt, and if I wore the same old one? Would people think I’m immature or selfish for not wanting to maintain a relationship with that friend who had hurt me so much, and is still behaving the same way?

Whenever this happens, I’d quickly remind myself that “the only person you need to please is yourself.” Even if there are people who are unhappy at me for the choices I make, so what, right? Life is short, and the only life I can live is my own. I trust myself enough to make the decisions I think are best.

Prince purportedly said, “A strong spirit transcends rules.” But perhaps a truly strong spirit transcends the need to be loved by everyone. Maybe freedom isn’t in being admired, but in being at peace with yourself, no matter who’s watching. That is the only real performance that matters.

Even now, years after his passing, Prince’s vault literally contains over 8,000 unreleased tracks — enough to release a new album every year for the next century. Here is a lifetime spent proving, perfecting, and seeking approval, and yet, the music remains unheard.

Perhaps that’s the greatest irony. The man who fought so hard to control how the world saw him left behind a legacy of music that the world never got to see.

If he had known the world would never stop watching, would he have finally allowed himself to rest? Or would he have kept playing, forever chasing an applause that was never loud enough?

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