Lessons in Leadership with Oprah Winfrey

“We can’t become what we need to be by remaining what we are.” –Oprah Winfrey.

Praised by many as “the queen of media,” Oprah Winfrey has broken through glass ceilings and industry gatekeepers to become one of (if not the most) influential women in entertainment. 

Spanning across television, film, print, digital, and podcast channels at the helm of her own 2.7 billion dollar network, and as the first Black female billionaire, Oprah has demonstrated timeless skill and strategy for telling the right stories. Her leadership in entertainment and philanthropy has inspired me to search for and share the right stories. 

Airing for the first time in the fall of 1986, The Oprah Winfrey Show went on to provide 25 years of inside looks at the lives of everyday people, their communities, cultural trends, literature, food, and celebrities. So, one would think that it was in the hundreds of episodes over two-and-a-half decades that I grew to deeply admire Oprah. But while I have some hazy memories of catching some of my favorite celebrities on her “What’s the Buzz?” segment in the early 2000s, it was in 2018 that I was inspired to lead like her.

In 2018, Oprah was honored with the Cecile B. DeMille Award for “outstanding contributions to the world of entertainment” at the Golden Globes. It was an exposing year for Hollywood, as the decade-long #MeToo movement gained major traction and thousands of women worldwide united against sexual harassment and assault. In her acceptance speech, Oprah, known to everyone around the world, spoke directly to me. 

In true Oprah fashion, she seized the time to look beyond the very accomplishments the award recognized and instead used the opportunity to tell the story that truly matters and one that must be heard. In the few minutes of her speech, she spoke with elegance and conviction about the historical and enduring strength of women at a time when people around the world were slowly but surely starting to remember our power. 

It was during this speech (I highly encourage you to watch, if you haven’t already) that my vision for the leader I wanted to become was made clear. Oprah was selfless with her time, her words, and her career. She made a name for herself by lifting others and creating social change, vulnerability, learning, and empathy her focus. 

In that speech, as she’d done throughout her career, she showed me and other young women around the world that standing for what you believe in, informing those around you, and choosing your words wisely were essential for creating paths for others to follow. 

Her unwavering determination to rise above trials and tribulations in her life and career pioneered a path for women to use their social, racial, and economic challenges as catalysts for storytelling and motivators for success. With that, throughout her career, she has committed to fostering Black and Brown talent, invested in hundreds of communities, and stood proudly and adamantly for social justice. 

Oprah’s talent in weaving together great cause and creativity has shown me that the best leaders don’t just do what they do very well, but they do it with passion and purpose. 

So, while her financial wins are strong, her accolades run deep, and her notoriety is abundant, her success means more to young women like me––for whom, in the early stages of her digital marketing career, storytelling in the vastly competitive field of online media requires newfound care, curation, and creativity.

For this year’s Women’s History Month, let’s reflect on how Oprah’s success as a woman, entrepreneur, and journalist taught me three foundational things about life and work.

1 –“Passion is energy. Feel the power that comes from focusing on what excites you.”

Don’t do work that is misaligned with your values and your interests. Whenever possible, prioritize work, hobbies, and activities that energize you. Passionless work is time wasted. As a leader and a storyteller, success is defined by living in your truth. Radiating passion and purpose will not only sustain healthy work habits and relationships but will ultimately create lasting and impactful projects.

2 –“Turn your wounds into wisdom.”

Be motivated by your discomfort. Whether you’re unhappy with where you are personally or professionally, remember that the objective is growth. Setbacks are inevitable, and they are not signs of defeat. Instead, they are reminders that you have made progress and that you will again. So when you’re faced with an opportunity to learn, grow, and succeed, commodify your pain to power. Admit when you don’t know something. Ask for help. Holding yourself accountable. Finally, remember there is no golden ticket, only your consistent willingness to learn and perform.

3–“Surround yourself with only people who are going to lift you higher.”

While being the frontwoman of her own brand, Oprah has made it clear she hasn’t succeeded alone. She has famously connected with audience members and fans alike. But perhaps most importantly, she has built long-lasting relationships in her industry, opening herself up to learn and collaborate with influential and dynamic people. She’s reminded the world time and time again that it is through these cherished, career-defining relationships that she has been reminded of her happiness, lifted from her sadness, and freed from the sense of loneliness on the leader’s road.  

About the Author

Cybele Ramirez

Cybele is a content strategist based in New York. In the startup space, she’s helping innovative new companies tell their stories online. She studied Culture and Media at The New School, where she Mastered the cross-section of social impact and technology. She enjoys covering the digital zeitgeist and writing to educate on emerging media.