The Millionaire’s Trap: Why Success Makes You Stupid

Here’s what really gets me – I’ve made millions trading, and I’m still sitting there adding to losing positions, as if I’m some rookie who just discovered options.

Still convinced that this time it’ll work out. Because apparently when you’ve had enough wins, you start thinking you can trade your way out of anything.

Bad position? Add to it. Chart not working? Must be timing. The setup is still valid, right?

Wrong. Sometimes the setup is fine and you’re still going to lose money. That’s the game.

See, this is the trap that successful traders fall into. You’ve got enough wins under your belt that you forget what it feels like to be completely wrong. You start believing your own hype.

“I’m a good trader, therefore this trade will work.” That’s not how markets work, but try telling that to your ego when you’re down on a position.

The “When in Doubt” Rule I Keep Forgetting

You know what the worst part is? I keep telling people “when in doubt, go further out in time.” Great advice, right? But did I follow my own rule that week? Of course not. I’m sitting there with short-dated options watching them expire worthless while giving other people advice about proper position sizing.

I really, really need to listen to myself more.

This is the difference between knowing what to do and actually doing it. Every trader who’s been around long enough has rules they’ve learned the hard way. Mine is simple: when you’re not sure about timing, give yourself more time.

But when you’re in the middle of a frustrating week, when every trade feels like it should work RIGHT NOW, you forget your own rules.

That’s expensive education, right there.

The Stubborn Conviction Problem

The crazy part is, I can still look at charts and see setups. My conviction hasn’t changed. I still think certain patterns are going to work. But now I’m second-guessing myself on everything.

Am I seeing something that’s not there? Am I forcing trades just because the markets are open?

This is what separates profitable traders from everyone else. When you’re wrong, you don’t stop seeing opportunities. You just get more careful about how you size them.

You go out in time instead of focusing so much on weekly options. You respect your stop losses instead of “hoping it comes back.”

But man, it’s hard to trust yourself when literally everything you touched turned to garbage.

Why I’m Not Blaming Jerome Powell

Here’s what though – at least I’m honest about it. When everything goes wrong, I’m not going to sit here and blame the Fed or geopolitics or market makers or whatever. It was my problem. My trades. My decisions.

And that’s the difference between traders who survive and traders who blow up. When your trades don’t work, the first question isn’t “what’s wrong with the market?” It’s “what’s wrong with my process?”

Maybe I was forcing trades. Maybe I was playing too short-dated. Maybe I wasn’t respecting support and resistance levels like I should have.

But the market wasn’t broken. I was.

The market doesn’t care about your mortgage payment or your kid’s college fund or the fact that you just had three wins in a row. It’s going to do what it’s going to do, and either you adapt or you get steamrolled.

YOUR ACTION PLAN

Here’s what I know after years of doing this: how you lose matters just as much as how you win.

You can have a bad week and learn something. Or you can have a bad week and blow up your account. The difference isn’t luck or skill or market conditions. It’s whether you can admit when you’re the problem and adjust accordingly.

I’m still seeing setups. Still convinced that good trades are out there. I could be dead wrong about everything, but I’d rather be wrong with conviction than right by accident.

Because in this business, the market is always teaching. Sometimes the lesson is “you’re right, here’s your money.” Sometimes the lesson is “you’re an idiot, pay attention.”

Both lessons cost money. Only one of them is optional.

Look, I may be completely wrong about my recent reads on the market. But there’s one thing that keeps working even when everything else goes sideways.

I call them “Opening Bell Aftershocks” – explosive moves that happen in those first crucial minutes when most traders are still figuring out what happened overnight.

Even during my worst stretches, these quick opportunities keep showing up. Like that recent APP trade that hit 334% in just 11 minutes after the opening bell.

See How It Works – For Free