The Millionaire Teacher As An Outlier—Part I

Next month I’ll be starting a unit with my 10th grade English class that my colleagues and I call “The Outlier Unit”, involving family research with a foundation based on the theme of Malcolm Gladwell’s bestselling book, Outliers

My students are socio-economically privileged.  They attend a very prestigious school in Singapore,  and most of them have done more globetrotting at 15 years of age than the average professional adult ever will.

But how did they get to their respective positions of privilege?  I open this grade 10 teaching unit by asking them, and these are the responses I typically get:

  1. My parents worked really hard and they were successful after getting into a great college
  2. My grandparents worked really hard and my parents benefited from their success

Very few of them find or believe that they’re where they are because of their great-grandparents.  And when they dig back into their family history, they generally realize that wealth, as the Chinese proverb suggests, doesn’t last three generations.  Modern studies support the proverb.  So the vast majority of wealthy people (or high income people) today are “newly rich”.

But after hearing my students define their positions as a result of their families’ hard work, I burst their bubbles.  I suggest that there are millions of people who worked harder than their parents or grandparents, but didn’t climb the socioeconomic ladder. 

“You,” I suggest to my students, “are outliers”.

Malcolm Gladwell suggests that there’s usually a catalyst of luck, coupling with hard-work to produce traditional success.  And when my students research their family histories, they can usually find that catalyst.

In Gladwell’s book, he uses professional hockey players from the NHL as an example.  Most of them were born in the first half of the calendar year, with a disproportionate number falling in January, February and March.  As luck would have it, they were born earlier in the year.  So a kid born in January 2000, is nearly 10% older than a kid born in December 2000.  Naturally, most kids born earlier in the year will be more developed:  stronger, slightly more confident, potentially more coachable.  Not differentiating the age differences, the stronger kids are then put onto the premier teams, with better coaches, more ice time, greater support….and before you know it, the gap between kids born in January, February and March, widens, as an aggregate, compared to kids born in October, November and December.

That’s one of the reasons most professional hockey players in the NHL were born in the first half of the year.

Gladwell does emphasize something he refers to as the “10,000 hours” of practice that extremely successful people typically endure before they become great.  But luck can determine who gets that 10,000 hours of practice opportunity.  It’s not just a matter of skill.  Sometimes it’s a lucky contact a person makes with an influential person.  During other times, it’s a matter of fortuitously being in the right place at exactly the right time.  It reminds me a bit of the movie Sliding Doors,  where the actress, played by Gwyneth Paltrow either gets onto the subway or misses it.  The film follows or parallels her life, based on that one difference.  What happens when she gets on that subway?  What happens when she misses it?  Our lives are no different.  Opportunities often spring from luck, even when we don’t realize it.

As a millionaire schoolteacher who has just written his first finance book (to be published by Wiley Publishing in May) I’m also an outlier.

True, I paid for my own college expenses, was never given a financial handout and amassed a million debt free dollars by saving diligently and investing well, but I’d be remiss not to examine the “Outlier” components of my success.

I’ll explore that in Part2.


Andrew Hallam

I’m a financial columnist for Canada’s national paper, The Globe and Mail, as well as for AssetBuilder, a financial service firm based in Texas. I’m also the author of Millionaire Teacher: The Nine Rules of Wealth You Should Have Learned in School and Millionaire Expat: How To Build Wealth Living Overseas. My mission is to educate, motivate and inspire people on basic retirement planning and best practices for investing, using evidence-based strategies. I'm happy to comment on your questions.

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10 Responses

  1. DIY Investor says:

    Gladwell is one of my favorite authors and "Outliers" is my favorite book of his. I think that most all of those we put on a pedestal in the investment world were lucky" to a great extent in that their market happened to occur at a certain time and they got some insight into their market by luck. Buffett talked his way into Columbia Business School to take a course with Benjamin Graham. Today, or with a different Dean of Admissions, it probably wouldn't happen.

    I am reading "The Big Short" by Michael Lewis (another great read !) and one of the stories is of a couple of nerdish guys who make millions starting with a $100,000 Schwab account and stumble upon the credit default swap market and start analyzing individual subprime mortgages. A different place and/or a different market and those guys would have just been more of the unusual characters in the investment markets.

    The important point I think Gladwell makes is that putting in the hours is a necessary condition. The Beatles wouldn't have been as great except for the many hours playing live in Germany. But putting in the hours isn't sufficient. You do need the "break".

  2. Barry says:

    There's another similar movie called "Run Lola Run" that shows different outcomes based on timing, similar to the movie you speak of. It's amazing how being in the right place at the right time can totally change the trajectory of a life.

  3. Think Dividends says:

    Looking forward to reading your book.

  4. Nice post Andrew. Indeed, if you're a teacher AND a millionaire (now), you're an outlier.

    All kidding aside, while luck had some role to play in your good fortune, literally, you're 10,000 hours of practice came from years of frugality, learning and finding out what worked (and what didn't) for you as an investor. Nothing in life can replace being in the right place at the right time, but to be where you are now financially, I think a great deal had to do with your 10,000 hours of experiences and seizing opportunities along the way.

    Really looking forward to reading your book.

  5. @DIY Investor

    Hey Robert,

    We have similar tastes in books. I really enjoy Gladwell's stuff, and The Big Short is an extremely entertaining read. Lewis is a great storyteller, and it's not the first time I've been captivated by one of his books. Liar's Poker was also superb.

    As for the Beatles, it was a good thing they cut their teeth in a bar full of drunkards. I heard that they were pretty crummy when starting out. If they had tried for an earlier record contract, they might not have made it.

  6. @Barry

    Hey Barry,

    I've heard of the film. Is it worth checking out?

  7. @Think Dividends

    Hey Think Dividends,

    Thank you. The reviews have been great, so I'm really happy about that! I'm looking forward to its publication.

  8. @My Own Advisor

    Thanks Mark,

    I do think you're right. To do well, the stars have to align along with the work ethic.

  9. Yakezie says:

    Congrats on the book Andrew! Would love to do a book review on and help profile it.

    I'm not sure if we are outliers. I know SAS obviously has a boatload of rich families… however, all I see around me here in SF is success. Hence, in my mind, there are no outliers. There are simply those who want it more, or don't really care and are happy with what they have.

    To me, everything is rational.



  10. @Yakezie


    Even in SF, you might be an outlier without knowing it. My guess is that you most certainly are. What you see around you are nice homes, nice cars, and people with high salaries, in many cases. What you might not be seeing are the credit card bills, mortgages and other personal debt.

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