A Story of Privilege

What I learned from two episodes of My Next Guest with David Letterman

Busayo Durojaye
3 min readMay 31, 2020


Meaning: a special right, advantage, or immunity granted or available only to a particular person or group.

Synonyms: advantage, benefit, prerogative

Courtesy Netflix

Every time I listen to a celebrity or high-profile interview, I’m always looking out for their admittance of some unearned privilege as a factor in their rise to success. I’ve been this way since Malcolm Gladwell’s Outliers echoed and emboldened some of my sentiments about success and inspired me to share my views from a biblical perspective in my article Time & Chance. The central idea is that Life gives undeserved, unearned privileges.

In an episode of My Next Guest Needs No Introduction with David Letterman that had Former US President, Barack Obama as a guest, I found exactly what I was looking for. Towards the end of the interview, President Obama said:

“Don’t you say to yourself, ‘Boy am I lucky’? And one of the things that I think I always am surprised by is when I see people who have been successful in business, or entertainment or politics and they’re absolutely convinced that it’s all because they were so smart and I’m always saying, ‘Well, look, I worked hard and I’ve got some talent but there are a lot of hardworking talented people out there’. There was this element of chance to it. There was this element of serendipity…And the reason that for me at least, is important, is so: A, I don’t feel too self-important, but B, you know, you want to see if you can maybe figure out how to sprinkle that stardust on other people.”

First, he admitted his privilege, and second, he knew the responsibility he had, to extend it to those who haven’t been as lucky as he is. That for me sums up life and how we are to play in it. We accept the privilege we have been given and then we share it with others.

Courtesy Netflix

In Letterman’s interview with Jay-Z, there was a conversation about a trip to London that saved Jay-Z’s life. That story, just like President Obama’s statement, caught my attention. Here’s the backstory — Jay-Z sold illegal drugs in his neighborhood as a kid, this was common where he grew up. According to him, it was his ‘paper route’. He did that alongside pushing a rap career which also was a very common phenomenon. In a fortunate turn of events, he got an opportunity to travel with a friend, an aspiring Artiste, to London for a studio recording with a hope to produce a record. The deal turned out to be a hoax but it was within the two months he was away that his neighborhood got raided by law enforcement which led to thirty of his mates including his best friend (who he usually was with every day) being arrested and jailed. His best friend spent eleven years in jail. Jay-Z admitted that if he hadn't made that trip, he wouldn’t be who he is today.

A fake music recording trip to London for two months was Jay-Z’s escape from a negatively life-altering event. That to me is chance, nothing else. This is why I believe there are no self-made people just lucky people. Yes, you could say Jay-Z is talented, works hard but when you put all that against the backdrop of one lucky escape he had as a kid, they are insignificant.

President Obama’s statement which I quoted was part of a question he directed to his host asking if he felt the same way; to which David Letterman replied, “I have been nothing but lucky”.



Busayo Durojaye

I am a big believer in People. If I can inspire one person through my writing, I’d think I’ve done a pretty good job. Twitter — @busayodurojaye