A few weeks ago, I was flying home from Denver with a scheduled 9:00 a.m. flight Los Angeles. My wife dropped me off at the airport around 6:00 a.m. My plan was simple: grab some breakfast, read the paper, catch up on a little work, and wait for my flight.
Then I noticed the 7:00 a.m. flight to Los Angeles had plenty of open seats.
I figured, “Why not?” I changed flights and was on my way an hour earlier than planned.
It turned out to be one of those small decisions that worked out better than I ever expected.
The Stories We Tell Ourselves
We all create stories about ourselves.
“I’m always the one who gets stuck in traffic.”
“My flights are constantly delayed.”
“I always get pulled aside by TSA.”
The interesting thing is that these stories often feel true because our brains become remarkably good at collecting evidence that supports them while overlooking evidence that doesn’t.
Psychologists refer to this as confirmation bias. Once we develop a belief, we naturally notice the events that reinforce it and pay much less attention to those that contradict it.
I’ve been making a conscious effort to challenge that tendency.
Paying Attention to What I Used to Ignore
That morning at the Denver airport, I was standing in the TSA PreCheck line as bags rolled through the X-ray machine.
The traveler directly in front of me walked through the metal detector.
A second later, the alarm sounded.
The TSA agent smiled and said, “Sorry, you’ve been randomly selected for additional screening.”
A few moments later, I walked straight through without any delay.
Years ago, if I had been the one selected, I probably would have added it to the growing collection of evidence supporting the idea that these things always seem to happen to me.
Instead, I noticed something different.
It happened to someone else.
A small observation? Absolutely.
But it reminded me that randomness doesn’t disappear simply because we experience one inconvenient outcome.
Sometimes You Pick the Right Flight
My new 7:00 a.m. flight departed on time and actually arrived in Los Angeles about twenty minutes early.
Later that day, out of curiosity, I looked up my original 9:00 a.m. flight.
Despite perfect weather in both cities, it had been delayed by more than two hours.
In the past, I’ve had plenty of experiences where I seemed to choose the “wrong” flight. This time, I happened to choose the right one.
Neither outcome proves I have good luck or bad luck.
It simply reminds me that randomness works in both directions.
The problem is we tend to remember only the events that reinforce the story we’ve already been telling ourselves.
The Road Not Taken
One of the most interesting things we can do is occasionally look at what would have happened if we had made a different decision.
Most of us never do.
We only experience the path we chose, so we naturally judge our decisions based on that single outcome.
But sometimes the road not taken provides valuable perspective.
It reminds us that life contains far more randomness than we’d like to admit.
It also keeps us from giving ourselves too much credit, or too much blame, for outcomes that were never fully within our control.
Investors Do This All the Time
The same thing happens with investing.
Suppose an investor sells one investment to buy another.
Months later, they know exactly how the new investment performed because they own it.
But how often do they go back and see how the investment they sold actually performed?
Usually, they don’t.
As a result, they’re evaluating only half of the decision.
Selling one investment isn’t simply deciding what to own next. It’s also deciding what not to own.
Without looking at both sides, it’s difficult to know whether the decision actually improved your situation.
Becoming a Better Decision Maker
One of the best ways to improve your investment decisions is to periodically revisit the important choices you’ve made, not to criticize yourself based on the outcome, but to evaluate the quality of your reasoning.
Did you sell because your investment thesis changed, or because the market became uncomfortable?
Did you buy because it fit your long-term strategy, or because everyone else seemed to be making money?
The goal isn’t to eliminate mistakes. That’s impossible.
The goal is to see your decisions more clearly.
We don’t become better investors simply by gathering more information.
We become better investors by seeing reality more accurately.
Sometimes that begins by paying attention to the evidence we’ve been overlooking all along.