Why It Hurts So Much  » TheTechnicalTraders

Most investors have felt it. 

That knot in your stomach when a stock you’re watching takes off without you… 
The frustration of selling too soon, only to watch the price surge higher… 
The internal voice whispering, “You missed it—again.” 

Oddly enough, missing out can hurt even more than losing money. And no matter how long you’ve been investing, that emotional sting doesn’t always go away. If you’ve been there, you’re not alone. The truth is, this has more to do with human psychology than market mechanics. 

Why Does Missing Out Feel Worse Than Taking a Loss? 

When we take a loss, especially one we expected or managed for, we have something to point to. We can explain the reason. We can make sense of it. 

But when we miss a big opportunity—especially one we almost acted on—it feels like a failure of judgment. It’s more personal. The brain doesn’t just feel the absence of gain—it perceives it as a mistake, a lost part of our future. And that can be even harder to let go of than a loss. 

It’s the “would have, could have, should have” that keeps us stuck. 

This emotional reaction is tied to something called loss aversion—but in reverse. Instead of fearing actual losses, we fear missing potential gains just as much, if not more. That fear leads to impulsive behavior, revenge trading, and self-doubt. 

The Emotional Shift: From Excitement to Regret 

Even locking in profits can feel disappointing. At first, we’re thrilled. But as the price continues to climb without us, the joy fades into frustration. 

“How did I not see it had more room to run?” 
“Why didn’t I trust my gut?” 
“Everyone else held on—why didn’t I?” 

That emotional swing—elation followed by regret—is fueled by unrealistic expectations. We tell ourselves we need to capture the entire move to succeed. Anything less feels like failure. 

And in a world flooded with bold claims, hot tips, and instant results, it’s easy to forget that real investing is built on long-term thinking, not short-term perfection. 

The Trap of Hindsight Trading 

One of the most toxic habits investors develop is hindsight trading. 

This happens when we look at past price action—after the fact—and start rewriting the story. We convince ourselves that the signals were obvious. That we “should have known.” That if we’d just done that one thing, everything would’ve turned out better. 

But decisions made in real time are never that clean. Hindsight gives us perfect information and zero risk—a fantasy scenario that distorts our expectations going forward. 

Worse, hindsight trading erodes confidence. It makes us doubt every decision and every method, because there’s always a better choice after the fact. 

Why Jumping Strategies Creates a Cycle of Defeat 

When people feel like they’re always missing out—or always getting it wrong—they tend to shift gears. They try a new method. Follow a different voice. Tweak their system. 

But here’s what usually happens: 
They leave just before their original strategy begins to perform. 
They enter the new one just as conditions start to shift. 
And the cycle repeats. Again and again. 

This constant switching guarantees one thing—you’re always out of sync. Always a step behind. Always playing catch-up. 

Eventually, you start to believe you just can’t win. 

As one of my subscribers put it: 

“I feel like a recovering addict—one day at a time, trust the plan, trust the process. I’ve never had a strategy that removes my emotional impulses the way this one does.” 

Another said: 

“Honestly, it took me several times of thinking I knew better… and yes, several times I gave up gains I had made because I refused to follow directions. I deeply regret that. Humility is key.” 

The Stories We Tell Ourselves 

We don’t just react to charts—we react to stories. Stories we hear from others. Stories we read online. Stories we tell ourselves about how we’re supposed to perform. 

And because most of us are emotional by nature—especially when money is involved—we tend to chase the next big thing or cling to positions that no longer make sense. It’s human. 

But often, our real motivation isn’t opportunity—it’s relief. We take action to soothe anxiety. We click the “buy” button because the silence is uncomfortable. We hold losing trades because it’s easier than admitting we were wrong. It’s not rational. It’s emotional. 

What Can You Actually Do? 

It starts with awareness. 

Acknowledging that emotions are part of the process doesn’t make you weak—it makes you honest. The goal isn’t to eliminate emotion. It’s to stop letting emotion lead. 

Ask yourself: 

• What part of the market do I find most emotionally difficult—missing out, losing, or sitting in cash? 
• What patterns do I repeat during uncertainty or fear? 
• When was the last time I exited a position simply because I felt uncomfortable, not because the strategy called for it? 

Recognizing your tendencies can give you just enough distance to interrupt them. 

Then comes consistency. Not the kind that demands perfection, but the kind that commits to a proven strategy even through the quiet stretches. A system only works if you give it time to work. 

If You Don’t Learn to Navigate This… 

If we don’t learn to manage the emotional weight of trading and investing, here’s what tends to happen: 

• We exit good trades too early, missing long-term growth. 
• We chase after losses, trying to “get it back.” 
• We freeze during pullbacks, afraid to move in any direction. 
• We quietly lose confidence, making smaller and smaller decisions until we stop altogether. 

But if we do learn to manage it, things change: 

• We stop reacting and start observing. 
• We hold cash without guilt, knowing it’s part of the plan. 
• We take wins without regret and losses without shame. 
• We build quiet confidence, not from always being right, but from responding well when we’re wrong. 

Final Thought 

No one escapes these emotions. Not the pros. Not even those who’ve been in the market for decades. But those who last—and grow—are the ones who learn to acknowledge their emotions, pause before acting on them, and commit to a framework that keeps them grounded. 

If you’ve felt the sting of missing out, the frustration of hindsight, or the cycle of switching strategies at the worst time, know this: 

You’re not broken. 
You’re not alone. 
You’re just human. 

And the more you understand that, the less power those feelings will have over your future. 

Chris Vermeulen 
Chief Investment Officer 
TheTechnicalTraders.com 

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