How Authentic is my Ambition?

During my first year of investment banking in New York, I always found myself at dinners filled with these other Canadian finance dudes.

We were all fresh out of school, eager to combat the omnipresent feeling of loneliness, and excited to buy dinners that didn’t arrive in plastic containers. I think the New York Canadian finance circle follows the Dunbar number principle – the community is roughly a size where it’s easy to meet everyone – so I went to many of these dinners.

Despite expending most of my mental energy on disguising the fact that I didn’t like my job, I noticed a clear pattern among the people I was meeting: most of my peers came from the same demographic background and ideological upbringing as me.

Like me, the vast majority of the people in this professional Canadian circle went to some unhealthily competitive public high school, had hard work instilled in them by their parents, and went to a university with an active investment club. A disproportionate amount of them were second generation kids from minority middle-class families and most of them were the only or eldest child.

Those patterns were also true for the majority of my investment banking analyst class, although the majority of Wall Street and the U.S. appeared to be more ethnically homogeneous (though where isn’t when compared to Canada).

Ambition feels like such a personal quest, because the hard work and sacrifices are borne alone. But meeting so many similar competitors forced me to question the authenticity of my motivations.

It’s possible that that’s just how the filtering process is supposed to work; the ecosystem solves and finds a specific person to fill a specific job, but I’m willing to play the cynic.

Seeing the ideological and biographical uniformity among me and my peers made me wonder how much of my ambition was actually my own.

Was it possible that my goals were just a byproduct of my circumstance?

The True North, Strong and Free

Before diving in further, I have to applaud the social mobility that exists in Canada – it is truly incredible and I took it for granted as a kid.

Canada ranks first in the world on social fluidity by the OECD and roughly 75% of Canadians end up in a different social class than their parents. Canada is the only country where a child of a manual worker is as likely to grow up to be a manager as they are to become a manual worker.

I think this primarily has to do with the quality of Canadian public schools, the relatively cheaper cost of university, and perhaps the large immigrant population (which I think forced a lot of parents to take underpaid jobs and depress their earnings).

To put it in perspective, the cost of my university tuition across all four years was roughly equal to the cost of a single year of some U.S. schools. I think there is also a much smaller disparity in the quality of universities and high schools in Canada vs. the U.S.

Per Maclean‘s, Canadians on average pay ~$20k CAD / (~$15k USD) annually on their fully loaded university costs. A year at an expensive U.S. school like NYU or Dartmouth costs ~$60k per year.

The canvas of social mobility and the theme of meritocracy evens the playing field for a lot of Canadian students. You don’t have to come from a top-tier background in order to have top-tier opportunities in Canada.

Being born Canadian, at least in my view, marginally improved my access to these opportunities, but that doesn’t really answer the real question: why exactly was I ambitious?

To answer this, I reflected on my evolving career mindset and the mindsets of my career peers.

I theorize that there are generally three main factors that contribute to one’s ambition: family, competition, and personal narrative. It seems that the strength of each factor tends to vary materially as one progresses through life’s stages.


When I’ve asked people in interview settings what it is that motivates them, the most common answer is without a doubt their parents – which I presume either stems from unresolved feelings of spite and / or a feeling of obligation to the family legacy.

It is no surprise that the most common source of ambition is family. Your parents raised you and played a big part in the first draft of your world view. They’re the ones who force fed you piano lessons and frequently reminded you how becoming a doctor would be the only definitive way into the family will.

In high school, I was certainly motivated by an uncomfortable and burning desire to impress my parents.

The phenomenon of family and culture motivation is well-documented and many of us are born into situations that prime us to care about status.

Two of the biggest influences on your level of ambition are the family that produced you and the culture that produced your family. There are no hard rules for the kinds of families that turn out the highest achievers. Most psychologists agree that parents who set tough but realistic challenges, applaud successes and go easy on failures produce kids with the greatest self-confidence

On the whole, studies suggest it’s the upper middle class that produces the greatest proportion of ambitious people — mostly because it also produces the greatest proportion of anxious people… It’s members of the upper middle class, reasonably safe economically but not so safe that a bad break couldn’t spell catastrophe, who are most driven to improve their lot. ‘It’s called status anxiety,’ says anthropologist Lowe, ‘and whether you’re born to be concerned about it or not, you do develop it.

Ambition: Why Some People Are Most Likely to Succeed by Jeffrey Kluger via Time

Parents understandably try to groom their kids for success and raise them in anxious environments that optimize for that likelihood. If you grew up watching your parents work hard to get you or keep you in the middle class, it makes perfect sense that you would aim for something higher.


An involved and potentially overbearing family can get you to a good school, but I suspect that the main factor underlying ambition (typically starting in the university years or shortly thereafter) often evolves to become competition.

Your parents generally know what schools are prestigious, but do they know which companies and which groups at those companies will get you the most attention from your potential mates? No, that’s for you and your peers to decide on and subsequently compete for.

When you’re surrounded by highly similar, highly competitive people, the most tempting thing to do is to adopt the most popular, community-approved goals. Don’t know what you really like? Well, these smart people all seem to want the same thing and if you’re smarter than them, you’ll beat them and you’ll get it.

Competition forces you to work hard.

How hard depends on how scarce or finite that desired resource is. Scarcity of anything – school admissions, jobs, parking spaces, attractive singles in your area – will raise the bar required of you and incentivize extra effort.

Competition turns ordinary tasks and evaluations into sports. It preys on the reward systems of Type A people and if left unchecked, coerces them into games they don’t genuinely want to play. If a particular outcome becomes so connoted with the idea of victory, then you don’t simply get that outcome, you get to beat someone.

I wonder in mostly zero-sum work environments like sales or public investing: do most people actually like their jobs or do they just like to win? Perhaps it doesn’t actually matter.

Personal Narrative and Identity

There will come a point in your career when your parents finally admit that it’s too late for you to pivot into medicine.

And eventually, that once insatiable feeling of competition you had with your peers will start to dull.

After my school years, I found that career progression felt much more like a journey taken in isolation. Most of the hard hours sacrificed are sacrificed alone and the paths of your friends will eventually become too divergent for you to compare yourself to them. In most arenas, the spirit of competition will become less and less clear, each person opting to play a slightly different game.

Whatever determination remains is whatever you’ve crafted as your own personal identity.

If you view yourself as a smart, hard-working, successful boy or girl, you will work very hard to protect that self-image. If you have a chip on your shoulder, as many of us do at the onset of our careers, you’ll work doubly hard in the hopes that you really are as smart as you think you are.

When burnt out finance people reach out to me or when my friends ask me to help them edit their writing, I generally feel a peculiar sense of obligation to help because I view myself as a helpful burnt out finance guy who enjoys writing.

I do think that to truly excel in your career, you have to like it (at least a little bit) and view your skill development as something to take pride in. It almost has to be your craft because eventually you’ll rise to a point where everyone else is there out of genuine interest.

Peak, easily the greatest book I’ve ever read on skill acquisition and self development, discusses how experts often enjoy pursuing mastery as part of supporting their self-identity.

Studies of expert performers tell us that once you have practiced for a while and can see the results, the skill itself can become part of your motivation. You take pride in what you do, you get pleasure from your friends’ compliments, and your sense of identity changes. You begin to see yourself as a public speaker or a piccolo player or a maker of origami figures. As long as you recognize this new identity as flowing from the many hours of practice that you devoted to developing your skill, further practice comes to feel more like an investment than an expense.

Peak by Anders Ericsson

Take Pride in Your Story

You really shouldn’t feel ashamed if you feel like you don’t have an authentic feeling of ambition towards anything. I’m not sure if I do. I actually don’t think passion is a realistic goal for most and I’m inclined to believe that many who preach passion are really just weaponizing a form of schadenfreude.

It’s a bit hokey, but I personally think sustainable ambition is most reliably found when you are writing and living a story you are proud to tell people about. You need to buy into whatever narrative you’re living and aim to be proud of the identity you’re working on.

2 thoughts on “How Authentic is my Ambition?

  1. Another great post Matt.

    Fwiw, I was talking to a friend, your name came up and they predicted they think you’ll be back in finance in 2 years.

    I have no opinion on that prediction but I really appreciate you sharing your experience for collective knowledge. A lot of my friends recently graduated and are also in the highly tracked finance or consulting route and I imagine this is the kind of post that will be relevant for them in about *checks watch* 2 years.

    I say all of that to say this. I write as well and I personally find that when people tell me they have read my writing it motivates me to keep writing more.

    Idk if you’re the same way, but please keep up the writing.

    You’d be surprised (or perhaps not) how many people younger than you from Ivey look up to you. These are things that profs and guest speakers tell us, but I think when they hear it from you it holds significantly more weight (or clout in vernacular ).

    I think you’re sharing very important ideas, that a lot people need to hear.

    (Also: you should consider video essays on YouTube or your IG story, it might also help with reaching a wider audience and connect more with your audience. That may not even be your goal with this blog but just thought I’d throw out that idea.)

  2. This is ridiculously relevant for a 2nd year investment banking analyst. Your blog speaks directly to me like its written to me.

    I hope you continue to make posts as these are extremely insightful and helpful as I think through my personal journey. Thanks!

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