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What Flying Taught Me About Fear and Investing

October 17, 2025

Fun Fact: I used to be a paragliding pilot in another lifetime.

The furthest I ever went was over 9 miles in Brazil. The highest I ever flew was about 6,500 ft in Turkey, and the longest I ever flew was roughly 2 hours in Chile.

When I was high above the clouds, all alone, I would find myself completely “in the zone." My monkey mind went silent, and it felt like a moving meditation. All that consumed me was the sound of the wind and the pull of my glider.

To be honest, though, it never entirely stopped being scary. But it did become a lot less scary. I got better at feeling the fear…and flying anyway. And, eventually, the fear softened to the point where I would find myself in moments of deep calm and even bliss. But I never stopped respecting the risk.

Fear is not entirely bad. It is what keeps us alive…keeps us aware. Without fear, we would make some terrible, even some life-threatening decisions. Fear isn’t weakness. It’s what makes us human. We would not survive as a species without it.

But too much fear can be paralyzing. This is true for many things in our lives, including money. The thing is, your brain is wired for survival, not stock picking. So if you are afraid to invest, it’s not irrational. It’s human. That fear you feel around investing often comes from a mix of psychological biases, including:

Loss Aversion: We feel the pain of losses about twice as strongly as the joy of gains. This makes us more likely to avoid taking action, even when the odds are in our favor.

Availability Bias: If we’ve heard a scary investing story recently (a crash, a scam, a friend who “lost it all”), that story feels more likely to happen to us. Even if it’s rare.

What happens without fear? This part is important because fear gets a bad rap. The truth is, if we didn’t have fear around investing, we might ignore all risks and make some awful decisions! Fear serves a purpose, but it just needs boundaries.

 When I learned to fly, I didn’t jump off a cliff and hope for the best. I had training, support, and a plan. I understood the weather, the risks, and the tools I had to navigate them. I knew where I was going and where I wanted to land.

Investing, like flying, may always carry an element of fear. The key is not to eliminate it, but to acknowledge it and put it in its proper place. Fear can serve as a guide, reminding us to proceed thoughtfully and stay grounded in our goals.

This quarter, I encourage you to reflect on how fear shows up in your financial life:

  • Where does fear influence your investment decisions? Does it keep you from taking action, or does it help you pause and plan?
  • In what ways can you reframe fear, not as a barrier, but as a reminder to invest with purpose and perspective?

By learning to work with fear instead of against it, you may find yourself not only more confident as an investor but also more resilient in pursuing your long-term financial goals.