Managing Creatives V: The Underdog

Sheldon Rocha Leal, PhD
6 min readOct 28, 2023

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by Sheldon Rocha Leal

As a kid I always remember watching television shows and being exposed to children that were highlighted as the future stars of a specific field. These were the up-and-coming vocalists, astrophysicists and authors of the future. These kids were marched onto various kid’s programmes and lauded for their brilliance. I was initially envious of these children, hoping it was me and wishing I would have my moment to shine on the screen. But I would often ask myself: are these people really brilliant and where will they be in 5 or 10 years time? The more these people were highlighted, the less convinced I was they were truly the torchbearers of my generation.

After a while a trend started to emerge, most of the people to whom we were being exposed, would disappear off the face of the earth, never to be heard from again. This is highlighted by a plethora of Hollywood kids that never managed to traverse the divide between being a child star and an adult superstar. Celebrated children like Corey Feldman from “The Goonies”, Emmanuel Lewis from “Webster”, Gary Coleman from “Diff’rent Strokes”, Macauley Culkin from “Home Alone” and Bobby Driscoll the original “Peter Pan”. I guess being under so much scrutiny, from such a young age eventually resulted in burnout. Furthermore, the expectation to succeed was too great and finally because these people were under constant surveillance they never really got a chance to fail or explore the full extent of their creative ability.

Corey Feldman (top left); Emmanuel Lewis (top right), Gary Coleman (bottom left) and Macauley Culkin (bottom right) were all child stars that didn’t navigate the transition from major childhood success to success as adults

The thing is that once a person attains success, it is unlikely that one will tamper with the formula that resulted in that victory. There is no room for exploration or failure. This can be limiting and constraining. After all the only way one can move forward, innovate and create is through failure, if that is not an option one is suppressed. After some reflection I started picking up that many times the underdog is the one who won out in the end. People like Cardi B, who struggled at school, came from an impoverished background and started her career as an exotic dancer, before becoming one of the world’s most successful rappers. Or Drake who was bullied at school, and eventually dropped out, starting his rap career as an independent artist and only getting his first record deal after the release of three mixtapes.

Another artist who fits this category is Taylor Swift, who although she was signed to a publishing and recording deal at the age of 12, with Sony, wasn’t really taken seriously at the company. She eventually left the contract and was signed to Big Machine Records in 2005, but her first album, “Taylor Swift” (2006), did not give us an indication of the star she eventually would become. It was only in 2008 with the release of “Fearless”, 8 years after she signed her first recording deal, that she struck platinum and her first of 12 consecutive No1 albums. She is now considered one of the most successful recording artists in history and the first to generate over $ 1 billion on tour.

Cardi B (top left), Drake (top right), Antoni Gaudi (bottom left) and Taylor Swift (bottom right) were all underdogs that landed up dominated their creative worlds

Antoni Gaudi one of the greatest artists and architects of all time and the creator of the Sagrada Familia in Barcelona, Spain failed many of his courses at university and his lecturers were sceptical about this career prospects. Debbie Allen who is one of the world’s most famous choreographers and dancers, was rejected from the North Carolina School of the Arts because it was claimed she had the wrong body type. Today she has 5 Emmy Awards, 2 Tony’s and a Golden Globe. She has additionally received a star on the Hollywood Walk of Fame and a Kennedy Centre Honour. Reflecting on the success of these underdogs I can only think that the thing that made them successful is the determination to succeed.

The drive and discipline to prove people wrong and the confidence in their ability are traits that resulted in their ultimate victory. No organisation, prize, award, or any other recognition would have been able to drive them to succeed. Furthermore, the freedom of being an underdog gave them the opportunity to experiment, try new things out, and develop the ultimate end product, without the scrutiny of people and their expectations. With no one expecting anything from them, they were liberated to excel and do their own thing. They were emancipated from the shackles of expectation and afforded the opportunity to fail to succeed.

Debbie Allen was originally rejected from Art school because she didn’t have the right body type to be a dancer and today she is one of the most famous choreographers in the world

Ultimately the hard work, discipline, and commitment to their craft paid off, and even though people did not expect much from them in the beginning, they were the ultimate victors. Very much like the fable of the tortoise and the hare. At a time and in a generation where instant gratification is king, it must be remembered that life is not a sprint, but rather a marathon. Whilst what you do may not be recognised today, does not mean it will not stand you in good stead in the future. Everything one invests in one’s brand are seeds that are sewed that will reap abundant rewards in the future. It is when one bases one’s worth on an institution and a person that one sets oneself up for failure, as no award, accolade or recognition can replace one’s integrity and contribution to one’s future greatness.

Although there are cases of individuals who successfully navigated the divide between early and overwhelming success and future victories, these stars were people who had a razor like focus on what they wanted to achieve. They would not allow anyone or their misgivings to stand in the way of their success. These include people like Michael Jackson, Jodie Foster, Justin Timberlake and Elizabeth Taylor. But when one looks at the stories of most iconic individuals in history, one often finds the story of an underdog. Individuals in whom few had faith, but who had such overwhelming belief in their own ability that they were willing to make the sacrifices necessary for complete triumph. Ultimately it is the attitude with which one approaches a situation and one’s brand development that wins out in the end.

There are some child stars that successfully navigated their transition into adulthood, but they had razor like focus: Justin Timberlake (top left), Jodi Foster (top right), Dame Elizabeth Taylor (bottom left) and Michael Jackson (bottom right)

Is it about the craft or about the recognition?! If the former, the battle is lost, if the latter then the sincerity from which the pursuit derives will articulate into long term success. At the end of the day, it is better to have long term victories than short term adulation, which are hollow successes. In conclusion, as Queen Latifah said at the 2016 Screen Actors Guild Awards as she accepted the award for her role in the 2016 Docu-Series “Bessie” about the iconic Blues singer, Bessie Smith, “You build your own boxes”. So what do you want your box to be, an open one where there are no limitations, or a closed one filled with empty victories?

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Sheldon Rocha Leal, PhD

Musicologist, Musician, Songwriter, Music Business Enthusiast and Music Teacher