How to Build Confidence in Your Portfolio Choices

The Slow Season of Confidence

Confidence is a strange thing. It rarely arrives when we need it most. More often it comes later—after the fear has had its say, after the doubts have circled around us like birds waiting to land. My son asked me recently how anyone can feel certain that the investments they choose will actually perform the way they hope. I could hear something familiar in his voice, a faint tremor I recognized from myself at his age. That uneasy space between wanting to make the right choice and fearing the consequences of making the wrong one.

If I’m honest, I still feel that sometimes. Even now. Even after decades of studying markets, of building portfolios, of losing and gaining and losing again. Confidence hasn’t been a gift the market handed me—it has been something I’ve had to craft slowly, like a small fire I return to each morning, coaxing it back into flame.

I told him that confidence doesn’t come from believing we know what will happen. It comes from understanding why we chose what we chose. There’s a quiet difference there, and it took me many years to notice it. The market doesn’t reward certainty. It never has. But it does reward discipline, patience, and a willingness to pay attention.

I think back to the early days, when every dip in the market felt like a personal failing, as if the numbers themselves were chastising me. I didn’t yet understand that fluctuation is the language of the market, not a sign of misconduct. And slowly, painfully, I learned that the more I understood the companies I invested in—their history, their drawdowns, their patterns—the less I feared the temporary storms.

Confidence grew in the places where understanding took root.

I tried to explain this to my son. How each decision is a step in an ongoing relationship with the market. How confidence builds in the repetition of choosing, observing, adjusting, choosing again. How over time those choices begin to reflect not just data, but insight—our own insight, shaped by experience, intuition, and even our missteps.

There is something deeply human about this process. We want guarantees, but the market offers none. What it offers instead is an invitation: to learn, to watch, to measure, to reflect. To cultivate a type of self-trust that isn’t dependent on always being right, but on knowing we made the best decision we could with the information we had.

I told him that relying on the Lunar Landing Portfolio is perfectly fine while he learns. That leaning on the structure I built isn’t weakness—it’s foundation. We all start somewhere, and most of us start by holding someone else’s hand for a while. But the goal isn’t to walk forever with guidance. The goal is to recognize the moment when your own judgment begins to stand on its own, quietly, without needing reassurance.

Confidence is not the absence of doubt.
It is the decision to move forward anyway.

And the more we practice choosing—carefully, thoughtfully, and with an open mind—the more that confidence begins to live in us, not as bravado but as calm. A stillness that says, I understand what I’m doing here, even if I don’t know what tomorrow brings.

That kind of confidence doesn’t arrive overnight. It grows like a slow season, one we barely notice until one day we wake and see how far we’ve come. And maybe that is the real lesson I want to leave with him: not how to always pick the best stocks, but how to trust the person he is becoming in the process.