How Wealth Allows Us to Act Fearless

Breaking the myth of the "Fearless" entrepreneur

Photo by Mahdi Bafande on Unsplash

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Here’s a narrative I want to smash into a million pieces; entrepreneurs are “fearless,” and anyone who stays at a 9-5 job long-term is a “sheep.”

I write about money, so I spend a lot of time on LinkedIn and “Money Twitter.” Every day I see some version of the following statement:

“You’ll never get rich trading time for money and the only thing holding you back from working from yourself is fear.”

Live shot of my reaction:

Here’s an alternative narrative I would like to start pushing:

We are as brave as our financial position allows us to be.

When I was dead-broke, I had crippling financial anxiety

In 2010, I graduated from University and entered the barren wasteland that was the post-financial crisis job market.

I had student loan payments that rivaled my rent, I was helping financially support my parents, who were hit hard by the recession, and due to said job market, I ended up continuing to work my summer job of driving rich people to their yachts.

I could write a lot of fancy words about what life was like at that time, but a GIF says a thousand words:

I had a lot of financial fear, and for good reason. People I love were depending on me, and I very much needed my paycheck, even if it was never enough.

Was I a coward for not dropping everything and “pursuing my passions?”

Nope. I was making rational decisions based on my present circumstances.

Mo’ money, less problems

Fast forward 10-years, when COVID hit, and millions of people were losing their jobs.

I just had my first child but I wasn’t worried.

Why wasn’t I worried when the COVID recession was arguably more terrifying than the financial crisis?

Did I transform from the cowardly lion into a fearless badass?

Nope.

Between 2010 and 2020, I increased my income, started a side hustle independent from my day job, and built up several years’ worth of living expenses in liquid assets.

I return to the thesis of this article: We are as brave as our financial position allows us to be.

When Will I become a full-time entrepreneur? When I have FU Money

After 4 years of writing about money online, I’ve met a number of former side-hustlers who are now full-time entrepreneurs. Do you know what they all have in common?

They never became full-time entrepreneurs until they were in the “position of F*ck you.”

The “position of F*ck you.” is perfectly articulated by John Goodman’s character in “The Gambler.”

Here is my favorite part of the monologue.

Did your grandfather take risks?

Yes.

I guarantee he did it from a position of F*ck You

It’s a hell of a lot easier to take risks and pursue your passions when you are operating from a position of F*ck You, the point where you have accumulated enough wealth where you no longer need to worry about how you would pay the bills if you lost your job.

We like to think that entrepreneurs are fearless and are so passionate about their business that they would risk it all to make their dream a reality.

What drives me nuts about this BS narrative of the “fearless’ entrepreneur is that almost every side-hustler turned full-time entrepreneur made that leap either because a job loss forced them to do it or because they were in a position of f*ck you.

Then they engage in the self-mythologizing and have you believe they made the leap without a massive safety net.

Side hustles and investing; that’s the slow, realistic path to the position of f*ck you

For non-wealthy people, side hustles provide the incremental path to becoming a full-time entrepreneur one day.

Here's how I'm doing it.

Step 1: Start a side hustle with scalable income (a product).

Step 2: Reinvest every penny back into the side hustle or into investments like stocks, bonds, and real estate.

Step 3: Aim to replace another 10% of my 9-5 income each year from the side hustle.

Step 4: Wait.

Wait until I have enough financial capital and side hustle income to cover my living expenses in perpetuity. At that time, I'll take the leap and become a "brave" full-time entrepreneur.

When I do, I promise you I won’t spin self-aggrandizing tales about how my only regret was not doing it earlier.

We are as brave as our financial position allows us to be.

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This article is for informational and entertainment purposes only. It should not be considered Financial or Legal Advice. Not all information will be accurate. Consult a financial professional before making any major financial decisions.