musings on career success: becoming rich and notable

See original post and follow up discussion on /r/slatestarcodex here

Recently, I have been reflecting on the idea of career success.

Specifically, there are individuals I know who have achieved success that I never anticipated, as well as a larger number of people I did expect to succeed but have not made any significant impact.

I don’t mean success in the context of living a fulfilled life or having a good job, but success in the context of becoming rich and/or influential.

For context, I am in my early 30s. I grew up in a very wealthy community in Toronto filled with lots of smart people.

When I was younger, I had this belief that I had a good sense of who, among those I knew, would become successful.

I thought success would follow two forms:


  • Be smart and hardworking > go to the best school/program you can > get the most prestigious job you can > work hard, climb the path and excel.
  • People who are exceptionally talented would be recognized as such and be provided an alternative path, more likely to lead to success.

I have a good job in the conventional sense (for someone living in Canada), but am very far from being rich, powerful or notable in any meaningful way.

I grew up with many people who went to top schools (in Canada and abroad) and became doctors, lawyers, consultants, bankers etc. and while nearly all of these people have good jobs, none of these people seem to be on the path of achieving real wealth or notoriety. Very few of this group are even working in jobs that would be considered high paying or prestigious in the American context. Perhaps this group will achieve more success in the future, but it seems that even the most successful in Toronto don’t have the opportunities to become rich or influential.

I know a few people who are rich and influential in so far as they work in their family businesses, a few more who are instagram influencers based on their appearance, and a few more micro-celebrities in localized communities. But of the actual people who became rich and influential, the list is composed of very different people than I would have expected.

I know a famous musician and an oscar nominated director, neither were viewed as precocious youths, or even today, despite their fame, as being particularly gifted. In contrast, there were lots of artsy people I grew up with that everyone thought were incredibly talented who never found success.

I know several people who founded moderately successful companies, none of whom were people viewed as being particularly smart, talented or likely to succeed while growing up. In fact, one person who founded a venture backed YC start-up was someone people were actively concerned about their future.

In contrast, none of the people I would have bet, the smart and hardworking conventional types, have become “somebodies”.

Three observations I have:

The first is that being smart, hardworking and conventional selects almost against this type of success. Anyone in my community who had the opportunity to go to a top school and get a prestigious job, did so. As a result, they dedicated their lives to pursuing this demanding career path, which left little room for other opportunities/exploration.

The second is that a very large number of people I know who became successful did so after moving to the US (NY/SF) and had their pathways altered there. This isn’t because the rich or talented moved to the US (almost all of the people I’m describing came from rich enough families to have moved to the US), it’s mostly the people who weren’t sufficiently engaged in their pathway in Toronto that moving to the US seemed like a worthwhile distraction.

The third is just how much luck and randomness was involved. To the point that in my honest observation, there is essentially no correlation between success and talent amongst those I know.

I suppose this is all tautologically necessary. Very few people are going to become rich and influential, especially so by their early 30s. Those that do are almost certainly going to have weird trajectories and be exceptionally lucky. While all of this makes sense, I guess I just never appreciated this when I was younger, in particular, the difference of being in Canada and the USA and how actually following the local maximum for success pushes one away from the global maximum.

I’d be curious to hear from others in this community. Are the people you know who became successful those you expected? Any success stories that surprise you? Did you notice a difference between those who went to the USA/your home country or went to nyc/sf from your smaller city?