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Oprah Winfrey: 6 life lessons with entrepreneurial wisdom

On Oprah Winfrey's 70th birthday, let's crack open her playbook and extract 6 golden lessons from the phoenix herself. Ready to turn your ‘talk’ into a thriving empire? Read along!

Oprah Winfrey: 6 life lessons with entrepreneurial wisdom

Monday January 29, 2024 , 8 min Read

A young sexually harassed girl rises from poverty and adversity to become a media powerhouse, philanthropist, actor, author, investor with a net worth of $2.8 billion and global icon. No, it's not a superhero movie– it's the incredible story of Oprah Winfrey. Forget “glass ceilings”– Oprah shattered every ounce of patriarchy and built a sky-high empire on the foundation of her grit, heart, and smarts. 

Was the journey from zero to billions easy? Definitely not. Did she give her entirety to reach the summit of success? Absolutely, yes!

But her success isn't just for admiring from afar. Packed within her journey are powerful lessons that any entrepreneur, at any stage, can employ to fuel their business dreams.

So, step into the boardroom of "The Oprah Effect." Ditch the suits and ties, because here, authenticity and passion are the power suits. On her 70th birthday, let's crack open her playbook and extract 6 golden lessons from the phoenix herself. Ready to turn your ‘talk’ into a thriving empire? Read along!

Oprah Winfrey Amazon India

Hollywood celebrity and talk show host Oprah Winfrey

Your past doesn’t frame your present

Winfrey's early life was marked by hardship. Born to an unwed teenage mother, she spent her formative years in rural Mississippi, navigating extreme poverty and neglect. At six, she moved to Milwaukee with her mother, only to encounter further challenges in the form of physical abuse and mental trauma. These harrowing experiences could have easily led her down a dark path, but Winfrey, with remarkable resilience, refused to let her past define her.

Instead of succumbing to despair, Oprah recognised the power of education and self-improvement. Moving to Nashville to live with her father and stepmother, she embraced his strict but loving guidance. This newfound stability, coupled with her inherent talent and determination, allowed her to blossom. She excelled in academics, winning awards for her dramatic recitation, and even claimed the title of Miss Black Tennessee at the tender age of 17.

Oprah's journey serves as a powerful inspiration for anyone facing challenges now. It is a story of resilience, of transforming past adversity into fuel for personal growth and achieving remarkable success. By choosing to focus on her potential and paving a new path, Oprah Winfrey not only reshaped her own narrative but also became a torchbearer for women facing abuse all over the world.

Find the guiding light within your soul

Self-discovery lies at the heart of a meaningful life, and understanding one's true essence illuminates the path to genuine fulfilment. This is a fundamental truth exemplified by the remarkable journey of Oprah Winfrey. For her, success and accolades are not the ultimate benchmarks, but rather byproducts of living out the "highest, truest expression" of herself.

While society and our closest ones have a certain perspective of us, when we delve beneath the surface of wealth, fame, and external validation, we encounter the profound question: who are we, at our core? What passions would still blaze within us in the quiet solitude of a world devoid of others? What unique gifts, yet unrealized, reside within our depths? These fundamental questions become the compass that guides us towards authentic living.

Oprah reminds us that passion is not merely a fleeting emotion, but a potent force – "energy," as she aptly describes it. By aligning ourselves with what truly excites us, we tap into a spring of motivation that propels us forward. Procrastination fades as the pull of purpose becomes our guiding light.

As entrepreneurs being the captains of the organisation’s ship, it’s of utmost significance to embark on a quest of self-discovery, silencing the external noise and attuning yourselves to the whispers within. 

Success doesn’t knock at your door overnight

Building a business is like building a house. You wouldn't start by putting on the roof, right? You'd first need to lay a strong foundation, build the walls, put in the windows and doors and then finally live in your dream house. It takes time and effort to do things right.

The same goes for businesses. Even with Oprah Winfrey, it still took her about 3 years to get her OWN Network up and running smoothly. She calls it her "TGFO" moment, which stands for "Thank God For Oprah!" because it was a lot of work!

So, if it takes someone like Oprah 3 years, it's probably going to take you, as a new business owner, even longer. That's why it's important to have a plan for at least 2 or 3 years, not just for the launch day. You need to make sure you have enough resources to support yourself and your business during that time, even if things aren't going great right away.

Remember, success takes time. Don't get discouraged if things don't happen overnight. Just keep working hard and building your business one step at a time. Just like that house, eventually, you'll have a strong and successful business that you can be proud of!

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Be authentic

Oprah Winfrey's journey exemplifies a fundamental truth often overlooked in the pursuit of success: authenticity. Her iconic talk show, initially echoing the sensationalist trends of the era, underwent a transformative shift after an episode. Witnessing the dehumanising spectacle of a woman's public humiliation, Winfrey made a conscious decision to restructure her show, aligning its format with her core values.

As she eloquently articulated in O Magazine, “I replaced the ‘If it bleeds, it leads' news philosophy with an intention that still guides me—to use the medium of television for its higher good."

This deliberate act of prioritising integrity over sensationalism marked a turning point. It shattered the notion that one must compromise one's values to achieve prominence. On the contrary, Winfrey's commitment to authenticity resonated with audiences, propelling her show to even greater acclaim and popularity, grossing over $125 million in its first year alone.

Oprah's story is a testament to the power of staying true to oneself. “I had no idea that being your authentic self could make me as rich as I’ve become. If I had, I’d have done it a lot earlier,” she reflects.

In an age saturated with filtered personas and fleeting trends, audiences crave authenticity. They can discern the difference between a carefully constructed facade and a genuine voice, and they gravitate towards the latter.

Master the art of the deal

Oprah Winfrey's ascent to billionaire status is not solely attributable to her charisma and media prowess. A cornerstone of her financial success lies in her exceptional prowess in crafting stunning deals.

Early in her television career, when offered a lucrative salary renegotiation, Winfrey dared to envision beyond immediate compensation. Instead, she negotiated ownership of her program, "The Oprah Winfrey Show," securing control over its content and destiny. This bold move laid the groundwork for her financial independence and empowered her to shape a media empire built on her terms.

Her endorsement deal with Weight Watchers exemplifies her keen understanding of leveraging personal brand value to mutual benefit. By acquiring a stake in the company alongside her promotion of their program, Winfrey secured interest in their success, ensuring that her well-being was intricately linked to the company's growth. 

This symbiotic relationship proved advantageous to both parties, with Winfrey's weight loss journey boosting Weight Watchers' stock and solidifying her financial gains.

Be grateful

Oprah's got a secret to success: saying "thank you!”

She believes in the simple philosophy–instead of whining about what you don't have, be happy with what you do. It's like magic– the more you appreciate what you've got, the more good stuff seems to show up!

Oprah gives away cars and trips to Hawaii, but you don't need to do that (unless you want to, of course!). Even a simple "thank you" to a customer, a birthday wish, or a handwritten note to your team can make a big difference. People like feeling appreciated, and it makes them want to help you win.

So, next time you see someone who did something nice, or you just feel lucky for something, don't forget to say "thank you!" It's a small thing, but it can lead to big things for you and the people around you.

Remember, Oprah climbed her way from the bottom to the top. And one of her biggest secrets is just being grateful for everything she has. So, give it a try! You might just be surprised at how much better life gets when you say "Thank you!"

Well, there’s more about this woman’s life that you can take a cue from. But that’s for another day. Wishing the powerhouse of success, kindness and smartness, the Oprah Winfrey, a very happy birthday!