How to Overcome the Fear of Failure in Business: A Hero’s Journey for Entrepreneurs

“In the end, the world didn’t really need a Superman. Just a brave one.”

-Superman (DC Comics)

Heroes Don’t Rely on Chance — Here’s What They Do Instead

Fear is a powerful deterrent—especially the fear of failure in business.

Most people never start the thing they feel called to create simply because they can’t stomach the idea of losing. And when you look at business failure statistics, the fear feels justified. The majority of new ventures never make it past five years.

Scary, right?

It’s easy to think of entrepreneurship as a coin flip: heads you succeed, tails you fail.
A binary outcome. A definitive pass/fail.

But that perception is an illusion.

If you study the arc of the Hero’s Journey—Joseph Campbell’s timeless roadmap for human transformation—you quickly realize that heroes never operate with binary thinking. Their journeys aren’t defined by winning or losing. Instead, they are cycles of departure, initiation, and return. Cycles of becoming.

And entrepreneurship follows this same pattern.

The act of becoming doesn’t have an end. And as Napoleon Hill (author of Think and Grow Rich) so wisely state: “There is no substitute for persistence. The person who makes persistence his watch-word, discovers that ‘Old Man Failure’ finally becomes tired, and makes his departure. Failure cannot cope with persistence.”

Whether you’re facing a broad fear of taking risks, specifically the fear of failure in entrepreneurship, or simply wondering, “Is starting a business worth the risk?” — the answer depends entirely on how you embark the journey.

Because heroes don’t avoid the journey out of fear. No one is ever truly 100% ready to take the leap.
But it’s the leap that grows them, if they allow it to. That’s when the transformation, internally and externally, begins.

Stages of the Hero’s Journey

The Hero’s Journey has three stages: departure, initiation, and return.

Starting a side hustle or primary business involves departure from the normal experience of the majority.
The initiation happens through the myriad challenges faced along the way, especially in the early stages.
The return can happen in one of two ways:
- This is the positive and lasting effect on the world through the success of the business.
- If at first one doesn’t succeed, they still possess a newfound power, knowledge and insight that they bring back to the drawing table for the next cycle—the next departure.

The Hero’s Return begins after the hero overcomes the ultimate challenge, often symbolized by a physical or internal battle that results in profound self-discovery. The benefit they’ve won—whether it’s wisdom, a special power, or a transformative perspective—carries the latent potential to reshape their world.

You’d think the return would be easy. But it actually requires a tremendous decision: to leave the extraordinary realm of adventure and re-enter the ordinary world.

It requires humility, compassion, resolve and courage.

But their experience of the ordinary world is no longer the same; it has become extraordinary due to their newly acquired powers and insight.

Departure: The Courage to Begin

Every entrepreneurial story begins the same way every heroic tale begins: with a departure.

This is the moment when you realize the life you’ve been living—your “ordinary world”—is too small for the person you’re capable of becoming. It’s the nagging sense that your gifts are lying dormant. That your ideas could make a difference. That you were made for something more.

It’s the moment when your heart whispers:

“I know there is a road out there with my name on it… but I’m afraid to take it.”

This is where the fear of starting a business meets you at the crossroad.
It’s the fear of leaving what’s known for what’s possible.

Most people never leave this stage.
They linger at the boundary line, endlessly replaying the same internal questions:

What if I fail?
What if I lose my money?
What will people think?
What if I’m not ready?

This is the first major encounter with the fear of failure in business. It’s the dragon that guards the gold.
Entrepreneurs often imagine catastrophic outcomes but fail to truly imagine what growth could look like—compounded for the rest of their lives. What sort of return on investment would one winning idea mean?

The reality is this.

Every hero must leave the proverbial village before discovering the world.

Initiation: Where Failure Becomes the Teacher

When an entrepreneur finally steps into the unknown—launching a product, starting a side hustle, opening a shop—this begins the initiation phase.

This is the stage where most people fear they will “fail.” It’s the most volatile stage of business: infancy.

But here’s the truth:

Failure in business happens to most. But you aren’t most.
Failure happens when failure is accepted.
The truth is: failure isn’t a dead end. It’s not all or nothing.
There are successes and failure, as with anything.
And failures, if perceived rightly, result in pivots to the business.
Regular course corrections—until the wings take flight.
It’s an initiation ritual.

In mythology, this is the place where the hero meets tests, allies, enemies, and temptations.
In business, this is where you encounter:

your first marketing flop
your first product that doesn’t sell
your first angry customer
your first unexpected expense
your first pivot
your first moment of wondering if you made a mistake

This is normal. It’s initiation. And only the strong-willed survive.

This is where the fear of failure in entrepreneurship shows up strongest, and why so many people freeze before ever taking the first step.

Superman’s Journey

Superman didn’t become Superman without learning to control his powers, failing, falling, questioning who he was, and standing back up each time.

Departure — He was sent to Earth from the doomed planet of Krypton.
Initiation — He grew up in Smallville, learning to control his superpowers—like strength and flight—while facing early challenges, like saving his town from a crisis or wrestling with his alien identity.
Return — Superman can’t go back to Krypton (it’s gone) but refocus his acquired powers for Earth’s humanity. As Superman, he shares his gift by protecting Metropolis.

At heart, entrepreneurs are no different.

Every challenge you face—financial, emotional, relational, or internal—is shaping you into a stronger, clearer, more capable version of yourself. This is where you develop the necessary entrepreneurial growth mindset through lived experience. This is where you learn to take risk in business not because you’re fearless, but because you no longer make fear the dictator of your decisions.

The world tells you failure is the end.
The Hero’s Journey tells you failure is the beginning of wisdom.
And as the ancient King Solomon observes: “Riches and honor are with [wisdom], enduring wealth and righteousness” (Proverbs 8:18).

Return: The Transformation That Changes Everything

After the trials comes the transformation.
And with it, the return.

The return is one of the most misunderstood parts of the Hero’s Journey. People assume that heroes simply come home victorious. But the return is actually much deeper:

It is the moment when the hero decides to bring their new wisdom, new strength, and new character back into the world that once seemed too small.

Think about Superman.
>He didn’t return to Krypton—it was gone.
>He returned to humanity.
>He returned with the power he had earned through trial, self-doubt, and self-mastery.

Every time he risks himself to save someone, he isn’t proving his invincibility. He’s living out his return—bringing his boon (his benefit) to the world.

Entrepreneurs do the same.

If your business succeeds, you return with something powerful:
value creation, opportunity, impact, provision for others, contribution to the world.

And the ability to apply that new skill and mindset over and over again.

If your business initially “fails,” you still return with something just as valuable:
knowledge, insight, resilience, systems, clarity, humility, self-awareness, strategy, and strength.

When you return from the first cycle—whether with profit or with lessons—you are not the same person. And it’s that person who is capable of building a business on stronger foundations the next time.

But this is important.

Failure doesn’t automatically make you stronger.

Interpreted correctly, initiation makes you stronger.

The return makes you wiser and connects you to purpose.

And the whole experience, whatever happens, makes you braver for your next departure.

This is how entrepreneurs grow after business failure—not by avoiding risk, but by engaging with it, learning from it, and carrying those lessons into the next cycle.

Why the Statistics Don’t Matter as Much as You Think

People obsess over why so many small businesses fail. They fear the risk. They cite statistics to justify staying safe, staying put, staying in their comfort zone.

But here’s the paradigm shift:

Failure only “counts” if you stop persisting.

If you stop trying.
>If you stop learning.
>If you stop applying what you’ve gained.

But as long as you keep walking the hero’s path:

Every setback becomes data.
>Every failure becomes a catalyst.
>Every mistake becomes a manuscript for your next step.

Those who only read books but never take action will never truly know what it takes.

Those who stay comfortable will only ever have theory (and probably incomplete theory, at that).

The world’s greatest entrepreneurs failed more than they succeeded—but they kept returning.

They kept growing.

Consider the words of Michael Jordan: “I’ve missed more than 9000 shots in my career. I’ve lost almost 300 games. 26 times, I’ve been trusted to take the game winning shot and missed. I’ve failed over and over and over again in my life. And that is why I succeed.”

So…Is Starting a Business Worth the Risk?

Only you can answer that.

But here’s the truth heroes know, and most people never learn:

It’s riskier to avoid your calling than to try and fail.

If something in you feels drawn toward creation, contribution, or entrepreneurship, then the call is already in motion. Ignoring it doesn’t remove the desire—it only buries it.

And buried callings become regrets.

The question is not:
“What if I fail?”

The real question is:
“Who will I become if I answer the call?”

Because when you follow the hero’s pattern—departure, initiation, return—there is no true failure.
Only cycles of growth.

What others might call failure, I call initiation. It’s just one step toward the ultimate goal. The key is not to allow failure to be final—and that’s a decision only you, the hero, can make.

An entrepreneur risks financial security, money, time and reputation to build a business, much like a hero venturing into the unknown.

The scary statistic about business failure loses its sting when you see risk as a cycle of personal and communal growth, not a coin flip. Every entrepreneur returns with a boon, whether it’s a thriving company or the wisdom for the next attempt. As the archetypical Hero’s Journey shows, taking risks isn’t about winning—it’s about growing, learning, and sharing to make the world better.

Heroes don’t rely on chance.

They rely on courage to answer the call.

And they focus on transformation above and beyond immediate success.

And you?
You might just be standing on the edge of your next great departure.

The Hero’s Step Forward

Ready to turn courage into action?

If you’re feeling the call to grow, transform, and rise above fear, your next step is waiting for you.

Join The Citadel — the guided, gamified journey through Budgeting Bayou, Investing Islands, and Entrepreneur Expanse.
You don’t have to do this alone. Join the community. I’ll be your guide.

Your map is ready. Your tools are waiting. Will you take the first step?