The Hero's Journey of an Investor: Why Struggle Leads to Financial Freedom

If you've been investing for a while or you're just getting started, you might feel like you're constantly facing challenges. Maybe you're doubting yourself, dealing with skeptical friends or family, or struggling to stay consistent with your investing practice. Let me tell you: you're not alone. What you're experiencing is part of what I call the investor's hero's journey.

In this post, I want to walk you through that journey—the same one I took, the same one my daughter Danielle took, and the same one thousands of our students are on right now. If you're feeling stuck, uncertain, or "late to the game," this is for you.

You're Not Late. You're Right on Time.

I often say that I get there eventually—just a little late. Danielle likes to joke that it's kind of our family motto. But here's the truth: it doesn't matter when you start learning how to invest. What matters is that you start.

Investing is a lifelong skill, and many of us come to it later than we wish. But in Rule #1 Investing, we believe the best time to start investing was yesterday. The second-best time? Today.

The Investor's Struggle Is Part of the Journey

The moments when we feel frustrated, disillusioned, or ready to quit are often the clearest signs that we’re being called to grow. I experienced this myself after years as a river guide. I loved the outdoors, but one season, I realized I had stopped showing up with enthusiasm. I was just going through the motions—and that was the wake-up call I needed to change my life.

That change led me to investing, but it wasn’t smooth. It required humility, perseverance, and an apprenticeship under my mentor. And yes, for a while I was cleaning toilets while I learned how to do this.

If you feel unfulfilled in your current job or doubtful about your finances, that discomfort might be life nudging you toward something better. Embrace it.

Investing Is a Hero’s Journey

Joseph Campbell described the hero’s journey as a universal path: you start in the ordinary world, hear a call to adventure, refuse it, meet a mentor, cross the threshold, face trials, find transformation, and bring wisdom back to your world.

Sound familiar?

In Rule #1 Investing, many of our students are reluctant at first. They think, "I can't learn to invest," or "That’s for someone else." Then they attend a workshop, take a course, or start reading the books. That’s the threshold.

You don’t have to fight Darth Vader, but you will face doubt—especially from the people closest to you.

The hero is the person who doesn’t give up in the face of uncertainty.

What To Do When People Doubt Your Investing Journey

This one hits home for my daughter Danielle. When she was first learning how to invest, she faced skepticism from friends and family. People asked, "What do you even own?" As if you can’t practice investing unless you already have a portfolio.

If you’re feeling that pressure, know that you’re not alone. It's okay to start with nothing but the desire to learn.

Keep going anyway.

Even Success Comes with Doubt

You might think that once you start making money investing, the doubt goes away. It doesn't. When I started managing other people's money, I felt enormous pressure. I was afraid I didn’t know enough.

Doubt can come after success, not just before it.

That’s why staying grounded in sound investing principles—like Rule #1's Four Ms (Meaning, Moat, Management, Margin of Safety)—is so critical. They give you confidence when emotion creeps in.

This Journey Can Be Generational

One of my favorite stories is from Mohnish Pabrai’s book The Dhandho Investor, where he talks about the Patel family, who came to the U.S. in the 1960s and now own over 40% of motels in America.

That’s the hero’s journey in action. And the beautiful thing is, once you learn how to invest well, you can pass that knowledge on. Your kids may not listen at first (trust me, I know), but the example you set matters.

The Struggle Is the Point

We live in a culture that hides setbacks. But every successful investor I know has faced failure, fear, and hardship. That’s normal. That’s growth.

Steel is forged in fire.

Keep moving forward. You don’t have to get it all right, and you don’t have to move fast. You just have to keep going.

If you’re starting this investing journey or feel stuck along the way, know that you're walking the same path that Warren Buffett, Ray Dalio, and yes—myself and my daughter Danielle—have walked. It’s the hero’s journey. And it's worth it.

Ready to Take the First (or Next) Step?

If you’re ready to learn how to invest with confidence, clarity, and purpose, we’d love to help you.

• Join our Rule #1 Investing Workshop

• Read our bestselling books

• Listen to our podcast, InvestED

You have what it takes. Trust the journey.