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Bad Kids, Good Leaders

Last week at Sloss Tech, I was afforded the unique opportunity to listen to Burton Rast, a renowned designer with a storied history at innovation powerhouses like Google and IDEO. As he spoke candidly about his early life, I found myself captivated by his reflections on being an outcast, a troublemaker, and, in his words, a “bad” kid. His story struck a chord with me, as I too was that so-called “bad” kid growing up. Misunderstood by teachers, barely tolerated by coaches, and the subject of whispers among parents, I was no stranger to police visits and seemingly endless detentions.

But beyond the rebellion and the mischievous grin, there was a curious and intelligent child, much like Burton. He shared how his upbringing had occasionally led to imposter syndrome in his professional journey. I vividly recall a moment early in my consulting career, sitting among the suits of a multinational bank, feeling like an outsider, haunted by my lower-middle-class upbringing.

Burton’s breakthrough came when a leader reassured him: “I know you think we’re pretty great, but we think you’re pretty great too.” While I never had such a defining revelation, over time I began to embrace my past, even flaunting it. I rocked a mohawk, sported tie-dye when I could, spoke more casually, and brought fresh, unconventional perspectives to the table. What I once viewed as weaknesses of my upbringing morphed into distinct advantages that have shaped me into the leader I am today.

Continue reading to discover how some “bad” kids have turned themselves into influential leaders.

Embracing Rebellion

One trait that is often misunderstood in youth is rebellion. While it may be seen as a sign of disobedience, it can also signal a natural tendency to challenge the status quo. Many business leaders who were once labeled as rebels have used that inclination to question and innovate within their industries.

For example, Richard Branson, the founder of Virgin Group, struggled with dyslexia and was known for his rebellious nature in school. This attitude, however, pushed him to challenge traditional business norms and create a global empire.

Resilience through Struggles

Life is not always easy for the misunderstood child. Facing constant judgment and criticism builds resilience, a key leadership trait. The capacity to rebound from failures and keep moving forward is vital in business.

Oprah Winfrey’s early life was fraught with hardship and abuse. Despite her struggles, she harnessed her resilience to become one of the most influential media moguls in the world. Her ability to connect with others and share her story has created a lasting impact on millions of lives

Empathy & Compassion

Children who have been labeled as “bad” often understand what it’s like to be judged or overlooked. This understanding fosters empathy and compassion – essential qualities in effective leadership.

Howard Schultz, the former CEO of Starbucks, grew up in a housing complex in the Brooklyn neighborhood of Canarsie. His understanding of economic hardship led him to implement progressive employee benefits in Starbucks, setting a precedent for large corporations.


The path from misunderstood child to influential leader is a journey filled with lessons that shape an individual’s leadership style. The very traits that were once misinterpreted as negative – rebellion, resilience, empathy – become the pillars of effective leadership.

By redefining what it means to be a “bad kid” and recognizing the potential within unconventional childhoods, we open the doors for a diverse and innovative generation of leaders. These are the individuals who will not only challenge the norms but redefine them, leading to a more compassionate and progressive business landscape.

In the words of Steve Jobs, another leader with an unconventional upbringing, “Here’s to the crazy ones, the misfits, the rebels, the troublemakers. The round pegs in the square holes. The ones who see things differently.” Perhaps it’s time we celebrate the misunderstood kids, for they may very well be the visionaries of tomorrow.

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