How Do You Know?
By Dennis Coon on July 29, 2026

A few summers ago, right in the middle of a July heat wave, our air conditioner stopped working. To make matters worse, we had family coming into town in just a few days, which meant this was not exactly one of those household projects we could casually put off until later.
We called an HVAC company, and the technician was able to get the unit running again. Before he left, though, he gave us a warning: “If it stops, that’s it. You’ll need a whole new system.”
Replacing an air conditioner is not exactly a small expense, so before making that decision, I called another company. The second technician listened to what the first had said, smiled a little, and replied, “That’s a bit dramatic.” He inspected the system, added some refrigerant, checked a few things over, and told me that if it stopped working again, I should simply give him a call.
That was three years ago. Our air conditioner is still running strong.
Now, that does not necessarily mean the first technician was being dishonest. He may have genuinely believed the unit was near the end of its life. It is 37 years old for crying out loud. But what stands out to me is not that one person gave a dramatic opinion and another person gave a calmer one. What stands out is that my instinct was to question it. Faced with such a large expense and a scary-sounding warning, I did not just blindly accept the first opinion. I got another one.
Most of us do that in other areas of life. If a mechanic recommends a costly repair, we may ask another mechanic to take a look. If a roofer says the entire roof needs replacing, we usually want someone else to confirm it. If a doctor recommends a major procedure, many patients want a second opinion before moving forward. The bigger the decision, the more natural it feels to slow down, ask questions, and make sure we are not being pushed into something by urgency, fear, or the confidence of the person delivering the message.
Yet when it comes to money, something interesting happens. Someone confidently predicts that the dollar is doomed, the market is about to crash, taxes will make retirement impossible, or one particular investment is the only safe place to be. Instead of treating that claim with the same skepticism we would bring to a furnace, roof, or transmission, many people accept it as if the prediction itself is proof.
I think part of the reason is that financial predictions are hard to verify in real time. If my air conditioner breaks tomorrow, we will quickly find out whose opinion was closer to reality. Financial predictions do not work that way. Someone can warn about an economic collapse for years before anything meaningful happens. Another person can confidently predict soaring markets, only to watch them fall first. There’s rarely an immediate scorecard, which gives bold predictions a lot of room to sound credible before reality ever has a chance to weigh in.
There’s also something very human going on here. Behavioral economists have long observed that most of us feel the pain of losses more intensely than the pleasure of equivalent gains. In plain English, losing money usually hurts more than making the same amount feels good. That is not a character flaw. It is just how many of us are wired. But it does explain why fear can be such a powerful sales tool. If someone tells us there’s a chance we could lose what we have worked so hard to build, our attention naturally follows.
That’s especially true in investing because there’s no alternate timeline. People often tell themselves, “I should’ve bought that stock,” or “I should’ve sold before the market fell.” Maybe. But there is no way to know what would have happened next. Would you have held through the volatility? Would you have sold after a quick gain? Would you have bought back in after the decline or waited until prices had already recovered?
No one knows. We tend to compare reality with an imaginary version of ourselves who made every perfect decision and managed every emotion flawlessly. That person does not exist. And that’s exactly what fear-based messages exploit. They ask us to imagine the disaster we could have avoided, the opportunity we could have caught, or the regret we will supposedly feel if we do not act right now.
In my experience, successful investing is not about making perfect predictions. It’s about consistently making good decisions. That means having a thoughtful plan, diversifying appropriately, managing risk, and, perhaps most importantly, keeping your emotions from making decisions your future self might regret. None of that is as exciting as a bold prediction. It doesn’t make for a dramatic headline. But it’s usually where the real work happens.
Clients occasionally ask me where I think the market is headed. The honest answer is that I don’t know. No one consistently knows what the market is going to do next month or which stock will be the next big winner. If someone truly had that ability, I doubt they would need to spend their time making bold predictions on television, producing endless YouTube videos, or trying to convince people they could see the future. Over time, their results would probably make the case for them.
The reality is that no one has that kind of certainty. That is why I do not believe successful investing requires perfect predictions. It requires good judgment. And good judgment usually starts with a simple question: “How do you know?”
Sometimes there will be a good answer. Sometimes there will not. Either way, when someone makes a bold financial claim, whether it is wildly optimistic or deeply pessimistic, I think it is worth slowing down long enough to ask the question. Your retirement deserves at least the same thoughtful skepticism you would bring to replacing your roof, repairing your car, or installing a new air conditioner.
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