The Privileged Boss

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My VERY EXPENSIVE noise-cancellation headphones can no longer block the whispers. The team members feel a particular disdain for me.

They think I have had it easy.

It is true that life bestowed privilege upon me. I went to a private school. I have never had to think twice before spending my money. Business class is non-negotiable for me.

I have grown up to be an entitled man. Confidence comes naturally to me. I am used to getting what I want when I want it. I like my privilege, and I like the attention that it brings me. I am bratty and inconsiderate of other people’s struggles and feelings sometimes. Or maybe most of the time. That is why my first girlfriend broke up with me.

You need to stop mansplaining and start putting in some real effort into relationships,” she had particularly noted. She also thought I was very self-centered.

Her feedback was hard to swallow, but there was some truth in it. To be fair, it is not entirely my fault. Many things have come to me easily, so I honestly don’t understand the need to put in the effort in every sphere of my life. But I have discreetly toned down my sense of entitlement since my first breakup.   

Other than that, I am successful. I work smart. I have the gift of the gab. Clients love me. I love them. 

I can understand why some colleagues would envy me for that. My father’s networks and his success have both helped my career. I do not deny it. I have not struggled like some of my self-made colleagues. They probably are the ones who resent me the most. I have heard them whisper, “What does he have to worry about? He gets chauffeured around the city”.  

But my colleagues just see the legacy associated with my name. They have no idea what it has cost me.

My destiny is not something I created; it was handed to me. I had no choice but to be the flagbearer of my family’s legacy. I have done that smartly, but it is still hard work. Yet, some people fail to see past my privilege when it comes to recognition. Is it possible for anyone to succeed just by virtue of being privileged? Give me some credit for my efforts.  

What is worse is that the same colleagues who despise me for my privilege often butter me up when they need introductions and access to connections. Why the double standard?

It is not easy being the son of high-achieving parents. Every day, I strive to be as good as them. In particular, my father. He is extremely strict. He has never told me, “I am proud of you.” All my achievements are inadequate in his eyes. I am constantly on the lookout for validation. I like colleagues who give me that ego boost.

I have let go of many dreams, passions, and desires. I was a national-level soccer player. My father made me quit that path to focus on academics. When I see young soccer players achieving success and being the poster child of mega brands, I resent my success. It was a dream that I sacrificed on the altar of legacy. 

It is painful to wake up every day and work towards justifying a privilege I did not ask for. I secretly crave the freedom to be who I want to be and aspire to muster the courage to chase my passions. I hope there comes a day when the world and I can see me for who I truly am – more than my father’s son. More than my privilege.


Food for thought: Have you envied your privileged colleague/boss? What behaviours can they demonstrate to become more endearing?

This post is authored by Nikki S, an aspiring author. If you would like to get in touch with Nikki S, please drop a line at

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