Dealing with “No”: How Steve Jobs, Oprah Winfrey and Michael Jordan Failed and Succeeded

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The entrepreneurial journey, which fascinates most but is lived by few, is one which is highly challenging. Dealing with rejection and failure is all part of the journey, but it is hard – painfully hard sometimes – to find the strength to keep going when it seems like doors are shutting.

One of my tactics to deal with “No” is to remind myself that I am not alone. Any successful person will tell you that they have been rejected at some point – and usually many times. Failure comes with risk, but so does opportunity.

Here are three stories of mega-stars who failed, persevered and became the icons we know them to be today. These stories show that “no” is not necessarily a roadblock, but a signpost along the way. How these individuals dealt with their failures is what was truly defining.

Steve Jobs

Steve Jobs is undoubtedly a modern icon. A game changer. A visionary. His recent death only seems to reinforce his legendary persona.

The reality is, however, that Steve faced multiple setbacks and failures throughout his career. Steve was fired from Apple as CEO in 1985. When he rejoined the company in 1996, he appeared to climb steadily back to his glory. He did in many ways, but had many failures too.

The Apple III computer in 1980, the Lisa (Computer) in 1983, The Cube (2000), the iPod Hi-Fi (2006) and most recently iAds (2010) all had disappointing, if not money-losing, results. However, each time Jobs learned from his failures, applied the lessons learned and created the next big thing.

Oprah Winfrey

Oprah Winfrey is known for her ultimate media savvy. She had the highest-rated TV program of its kind in history and became one of the richest African-Americans ever.

But the reality is that she endured a rough childhood, being shuffled between the homes of her grandmother, mother and father. At age nine, she began to endure sexual abuse by an uncle, cousin, and a family friend that would last for years.

After graduating college, Winfrey was fired from one of her first jobs as a reporter, being told she was “unfit for TV”. The problem? She found it hard not to share her opinions or be affected by sad stories – the empathy and authenticity she would later build her empire on.

Michael Jordan

Michael Jordan has been called the greatest basketball player of all time.

But this was not clear from the start. Jordan grew up in the shadow of his older brother, who was considered to be the better athlete. In his sophomore year, Jordan tried out for his high school’s varsity basketball team, but did not make the cut. Instead, they put him on the junior varsity team to develop his skills.

This failure drove him to work harder and, in his eyes, prove his worth. He quickly became the star of the junior varsity team and made the varsity team the next year. By his senior year, he made the All-American team.