Diana Richey, photo by Nat Hagood
Sometimes, we hesitate to take the first step toward something new because the thought of processing unfamiliar information feels exhausting. And even when we’ve already started, continuing can feel just as hard. The effort of staying with something difficult, especially when progress feels slow or uncertain, can feel frustrating and even overwhelming.
But why? Why does both beginning and continuing so often feel uncomfortable? Why does growth—even when we want it—feel like something we have to endure rather than move toward?
This past weekend, my husband and I went cross-country skiing in the national park. It was beautiful, with trees blanketed in snow and distant mountains dusted in white, pine trees peppered across the backdrop. The trail was hilly, and the snow conditions were challenging. I was falling constantly, using my poles to pull myself back up. I felt frustrated and embarrassed, and even fought back tears as I trudged along.
I’ve been downhill skiing since I was three years old. And although I’m newer to cross-country skiing, I’m thinking, “How hard can this really be? I’ve been on skis forever.” But as I talked through my feelings with my husband, I realized I was approaching each hill with an expert mindset instead of a beginner’s. Rather than embracing the challenge and treating each fall as part of the learning process, I kept thinking, “Why can’t I do this? I should be better than this.”
As I slowly shifted my mindset, remembering that I am always learning and that life is always a process of learning, I started to relax. I looked up and took in the quiet of the woods, the snow, and the rhythm of moving forward with my husband. I kept falling, but at a certain point, it became funny.
Investing requires a similar mindset. It is often framed as complex and intimidating, something only experts can navigate. But like skiing, every misstep is part of learning how to move. Each mistake and unfamiliar concept is an opportunity to understand companies, markets, and the economy more deeply.
Of course, none of this works without risk management. Because we’re human, one of the few guarantees in life is that we’ll make mistakes. Knowing that, I don’t ski no-fall terrain on my cross-country skis, and I never place a large portion of my life savings into any one investment.
It’s one of the reasons why I moved from international tax law to financial planning, and eventually to building my own fractal investment model. I am always learning, and that process has been deeply satisfying both intellectually and financially. It has helped me build resources that support a life I once only imagined.
With investing, there is no final expert level. The economy shifts, innovation evolves, and the terrain changes beneath you. But if you stay curious, open-minded, and consistently apply the fundamentals, you begin to find your balance. You start to look up from your footing. And, like on that snowy trail, you realize you are moving forward, falling sometimes, but always learning and building momentum.