A few weeks ago, I had to dress down a young man whom I’ve been trying to mentor. The background was simple. I had received feedback about his inability to file documents. He complained that he was being given “s**t” work, and when I asked him what he expected interns to do, he replied, “Go to events and meet big shots.”

When I tried to tell him that interns are not brought to events, he tried to argue that he was a “special intern” but backed down when it was clear that I would do him physical damage for giving me a wimp reply.

I recounted this story to one of my directors, who told me I was wrong to be upset by this attitude. My director’s point is that interns these days have “expectations” about the workplace, and I cannot expect them to have the mentality I had.

Well, here’s the thing: while I did take a knock or two, I don’t think I went through anything particularly harsh. As an intern at Citi, I didn’t want people to know I got the job because Daddy played golf with the department VP. Work was not glamorous – I spent a lot of time filling out Excel spreadsheets and photocopying cheques (this was back in 1999). Yet, I did because I was told this was what I could expect, and I was terrified that people would see me as a “rich kid” who got the job because Daddy had a string to pull.

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I don’t take the mentality I brought into Citi as an intern to be anything special. When I started working in a small agency, I needed to prove that I got the job and could do it, even though it was known that my dad had a brand of sorts in the industry.

So, I am aware of expectations. I am aware that coming from a well-to-do background has advantages. I know we live in a world where you must use every advantage you have, including those you were born into. However, you have to know the limits of those advantages. I find myself telling this young man the same thing I tell my daughter, “Being young and handsome/pretty can only get you so far.” Sure, good looks make it easier to get your foot into the door – but it won’t keep you there if you don’t do the work.

Yet, my director has a point. I belong to a different era, and the kids (my own included) think differently. I can’t expect kids to memorise a phone book because there’s no need to. We all carry handheld computers, which makes such skills irrelevant.

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However, I do believe that certain harsh realities don’t change. One is best summed up in the Celine Dion song “How Does a Moment Last Forever,” when there is a line about how we need bad times or our lives are incomplete.

I think of that line because there’s a truth there. We’re all happy and friendly to each other in good times, but things change when things get rough.

Taken from the movie “Renaissance Man”.

It’s this simple: my BFFs remain my army mates for a good reason. These were the guys who were there through some awful times. We got whacked together, and we helped each other out. Our memories of the things we went through were far from perfect, which made the bond we formed all that much sweeter.

There is a reason why I am so proud of my days as a freelancer. Sure, I went through the awful experience of working and not getting paid and being in a business and getting jobs done but not getting recognised because I didn’t have “experience.” All these experiences made me a wiser person, and although a decade of a steady job has made me financially more secure, I like the person I was much better. That guy had guts and passion. The guy I am today undoubtedly makes much better decisions.

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The memories that are inevitably sweet come from the most uncomfortable moments. If you ask me where my future lies, it’s inevitably with the people outside my immediate professional sphere. These guys challenge me to grow, and even as I approach the half-century mark, I know I can’t stop being challenged.

A lot of the young guys don’t see it that way. I had to tell the young man that he’s entering a world where he’s competing against people who are hungry and willing to do what it takes. Nobody will care about his family background and that cruising in the comfort zone is a sure-fire recipe to be eaten alive. Before he joined, his Godmother told me not to worry about him. The truth is I am terrified for him and his generation of kids who haven’t quite understood how challenging the world can be and how they need to be prepared to be constantly on their toes.


A version of this article first appeared at beautifullyincoherent.blogspot.com