Time to Be Fearful

It was not a wise thing to do—and it’s not an example I’d want my kids or grandkids to follow. But I’ll tell you a tale anyway. It’s a story of loss and comeback, of fear… and, truthfully, more fear. I guess confession is good for the soul.

Quite a few years ago, I noticed something simple: the price of gasoline was falling. From that observation, I made a leap. I began buying oil companies and energy ETFs. At first, I eased in. Then, one day, I didn’t. I committed a large chunk of my portfolio—far more than any reasonable person should—to this single idea.

And then the drop accelerated.

To keep things simple, let’s say I started with 100% of my investment. After the decline, I was staring at 50%. Just like that, half vanished—at least on paper.

I remember thinking, “Oh crap.” (One of my favorite semi-offensive phrases.)

Then I reached for a well-known investing rule: “The first rule is don’t lose money.” I told myself that if I didn’t sell, I hadn’t really lost anything. My account statement suggested otherwise. Still, I held on.

Eventually, the tide turned. Energy prices recovered. My battered position began to heal—and then to grow.

For some time now, I’ve been selling, little by little. I don’t know when the rise will end, so I trim in small amounts. But as prices climb and buyers seem eager, a new thought creeps in: “Oh crap… am I selling too soon? Too cheap?”

That’s the strange thing. I’ve made a substantial profit, yet the fear hasn’t gone away. It’s just changed shape.

When I was down 50%, I feared losing more. Now that I’m up, I fear missing out.

Here’s what I’ve come to believe: unless you are absolutely certain—borderline hubristic—you will feel fear when you step outside a traditional, diversified portfolio. The classic 60/40 mix doesn’t just aim to balance returns. It helps manage emotions.

I didn’t follow that path. I made a concentrated bet. It worked out—this time—but that doesn’t make it wise.

Uncertainty—and fear—are constant companions in investing. They show up when prices fall. They linger when they rise. They whisper when you buy, and they nag when you sell.

So what’s the lesson?

Not that you should swing big. Not that you should avoid risk entirely. But that you should understand what kind of investor you are—and how much fear you can live with.

Because in the end, the real risk isn’t just losing money. It’s making a mistake you can’t recover from.

Maybe you have a tale you can tell.