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The Privilege of Daring Greatly

In early 2004, a college student launched a new website. The site was a mix of a photo directory and a comment board, and it quickly gained popularity across campus.

The student soon opened access to other colleges, and he dropped out of school to build out the website further. He moved across the country to seek investment for his fledgling project. All while fending off lawsuits from jilted co-founders.

That college dropout’s name was Mark Zuckerberg. And the website he built was Facebook.

With the benefit of hindsight, Zuckerberg’s actions seem perfectly logical. After all, the corporate arm of Facebook — now called Meta — is now one of the world’s most valuable companies, with a market capitalization of $1.5 trillion.

But back in 2004, such surety was nowhere to be found. Back in 2004, Mark Zuckerberg was taking a massive risk in doing what he did.

Or was he?


In late 2005, I got an invite from a classmate to join Facebook.

I hesitated.

I had never heard of the social network. And for good reason.

Up to that point, Facebook was only available for users with a college email address. And as a high school student, I didn’t yet have one of those.

But now, Facebook was being opened up to adolescents. And my school was getting first dibs.

This was no coincidence.

You see, I went to the same high school as Mark Zuckerberg’s sister. We were even in the same Psychology class.

This wasn’t your average high school. It was a prestigious private institution attended by the children of wealthy elites.

I was not one of those. I was only getting this top-notch education because my parents taught in the Middle School — providing me a massive discount on tuition.

Mark Zuckerberg’s sister though, was not enrolled on a technicality. The Zuckerberg family was well off long before Mark launched his new venture. They could afford to send their daughter to this school, just as they could afford to send Mark to a prestigious boarding school a few years prior.

Mark Zuckerberg’s success with Facebook would later send the family wealth to stratospheric heights, of course. But he wasn’t exactly struggling for resources when he dropped out of college to turn his prototype into a full-fledged tech company.

I’m not bringing this up to pour cold water on Mark Zuckerberg. Plenty of others have done that over the years.

I’m simply pointing out that Mark Zuckerberg took his risks with a level of privilege that others didn’t have. Even if he fell flat on his face, he’d still have the means to get by.

That might seem like a footnote in the Facebook story. It’s anything but.


They say a house isn’t a home until there are decorations on the walls.

And some friends of mine have taken that to heart.

A mix of landscape scenes, artwork, and family portraits adorn the walls of the living room and hallways. And their kids’ bedrooms feature framed posters with inspirational sayings.

One of those posters reads Dream Big, Little One. And whenever I see it, conflicting feelings overtake me.

For I want that child to dream without boundaries — and to make those dreams a reality. But I know the challenges that lie in the way.

You see, dreaming big and taking risks are part of the American ethos. Without a caste system or mobility barriers in place, Americans are ostensibly all free to attain whatever they desire.

History books are littered with examples of rags-to-riches success stories. Pioneers. Prospectors. Oil barons. Industrialists. Innovators.

It all reinforces the idea that anyone can make big things happen here, regardless of their origin.

But the realities of capitalism tend to contradict that notion.

Indeed, no one will take a big bet seriously in this nation without collateral to back it. And those without assets have no means to pony up — leaving them little chance of leveling up.

Add to that the lack of a social safety net in our society, and the unbridled risk of going all in is just too big for many of us to manage. Getting it wrong could mean destitution or even death. And that’s too much for us to handle.

Daring greatly, it seems, is a privilege. An opportunity for the have-somes to get some more. But nothing more than a fanciful wish for the have-nots.

This might seem like a bitter pill to swallow at first. But a little perspective can go a long way.


About 80 years before my classmates introduced me to Facebook, my paternal great-grandfather walked the halls of his high school.

Our school buildings were about 150 miles apart, and our surnames were the same. But that’s where the similarities ended.

You see, my great-grandfather grew up poor. Raised by a single mother who worked as a street vendor, he had few avenues to success.

My great-grandfather made the best of his circumstances, becoming a successful grocer. One of his sons — my grandfather — went on to become a successful doctor. And one of his sons — my father — became a teacher at a prestigious middle school.

So, when it came time for me to leave the halls of my high school — my newly minted Facebook profile in tow — I had more opportunities to dare greatly than anyone who had come before me. I took advantage of that to a degree, trying my hand in the news media before building a marketing career from the ground up.

But the depths of my risk-taking only went so far. My family had made it to this point through incremental improvement, generation after generation. And I wasn’t about to mess with that formula.

I’ve been content to move the goalposts a bit further than before. I’ve dared a bit, but not too much.

And I’m better for it.

This just might be the formula for those of us without the privilege of daring greatly. Good enough can do more than suffice. It can help us progress at a steady pace.

But it can only unlock these outcomes if we let it. If we eschew the allure of the big bet and embrace practicality.

That is the path to sustainable success. Let’s make sure we follow it.

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