Fortune Favors the Bold

Or at least the people who try

My high school. Photo Credit: Colin Black

The Roman poet Virgil once wrote:

Fortuna audaces iuvat — fortune favors the bold.

I learned how true that was in my sophomore year Latin class.

My Latin teacher held a small contest and offered to loan a rare book to whichever student wrote the best essay on why they deserved that book.

We were all dismayed when he mentioned that the 1-page essay had to be handwritten and was due the following day.

Even though I had mountains of homework, and no real need to study yet another Latin book, I wanted to win.

It was a mix of personal pride, wanting to impress the teacher, and being genuinely curious about the book.

Sometime that night, I managed to crank out a couple of subpar paragraphs. It wasn’t amazing, but it seemed decent enough to submit.

When I turned in my essay, I was surprised when he immediately gave me the book.

I asked him why.

He said…

“You were the only one who submitted an essay.”

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The same year I was basking in the adolescent anxiety of sunny Southern California, a breakout author was publishing his first book.

In The 4-Hour Work Week, Tim Ferriss talks about how he was teaching a college course and challenged his students to write 3 famous people and try to get a response from at least 1.

All within 48 hours.

The first year?

No students even attempted the challenge.

They were afraid of getting rejected.

Or that other students would outperform them.

The second year?

6 of 17 students accomplished the challenge. One of them even reached Eric Schmidt, the then CEO of Google.

In the end, the task wasn’t really about who the students reached, or what the details of the response entailed. The task was about helping students get over their fear of failure and get a taste for trying absurd, out-of-reach challenges.

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The University of Notre Dame. Photo Credit: Colin Black

About ten years later, I ran into the same lesson again when I applied to business school.

At the time I was managing an online high school program.

As it turned out, just getting into business school was almost harder than school itself.

Here I was, a history major whose only experience was going to an unknown school and working for an unknown company.

I hadn’t taken a math course in 7 years. I didn’t know what a SWOT analysis was. I didn’t know the names of the big 4 consulting firms.

I just knew 3 things:

I liked reading business books.

I needed more money.

And I needed to change my life.

I just didn’t realize how much work it would take to actually get in.

I spent about 3/4 of my Saturdays in the office that year, between reviewing resumes for the many hires we were making that year and taking GMAT practice tests.

Despite all my studying, taking the GMAT twice and the GRE once, my scores were just okay.

Still, I had a solid GPA and experience managing a startup online education program. So, in spite of all my doubts, I applied to 4 schools and got into 2.

I’d had friends who told me to apply for lower-ranked schools, and I myself wasn’t exactly sure how my applications would turn out.

But I knew I’d never forgive myself if I didn’t at least apply for a few schools that I cared about, even if they might be out of my league.

Somehow, with my below-average math scores, terrible grades from senior year of college, and management experience at a tiny, unknown company…

I got into one of my dream schools.

I could hardly believe it.

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Looking back, the lesson from all three moments was the same.

Don’t be mistaken, saying “just try” doesn’t mean “just wing it.”

It only took me one night to write that Latin essay, but it took me a year to get into grad school.

No one should run a marathon without training first.

The work is hard. The work is scary.

But the work is necessary.

And the work isn’t as bad as it seems.

Spending every Saturday in an office for nearly a year isn’t fun, but it won’t kill you.

Writing an extra essay for Latin class when your normal homework load already gets you only 4 hrs. of sleep a night (welcome to Catholic school) won’t kill you.

Being embarrassed about starting a Substack or a YouTube channel won’t kill you.

And yet, not that many people are willing to undergo the struggle.

Most people would rather stay in a job they hate

than face the embarrassment of applying for a new job

or starting a company and failing.

But this is to your advantage.

Entrepreneurs like Tim Ferriss or Alex Hormozi will remind you that everyone is afraid of the big things. So not many people try them.

If you have a small goal, everyone might be willing to try for that goal, so you’ll have a lot of competition.

But if you have a big goal, or even a slightly absurd goal, not that many other people will be competing against you.

As Alex Hormozi likes to say, most people give up. So the bar has never been lower.

If there’s something in your life that you want to change, do something about it now.

Don’t die wondering what would have happened if you just put in the effort.

Everyone else is just as busy, scared, and uncertain as you are right now.

Most of them won’t even try.

Don’t worry about them. Submit the essay.

Just try.

You might fail.

But every once in a while, fortune favors the bold.

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Want more motivation like this?

Here’s one of my favorites.

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