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What Hurts You Most as a Trader? A Question Every Trader Should Ask!

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Hey there,

I had a fascinating conversation with one of my coaching clients recently that I think you'll find eye-opening. This guy is what I call an “anomaly among traders” – and the question he asked me completely reframed how I think about trading psychology.

But first, let me paint you a picture of this trader…

The Home Run Hitter

This client doesn't mess around with small trades. He's swinging for the fences, looking to make his entire year in just a handful of trades. While most traders focus on singles and doubles, he's hunting for home runs.

Here's what makes him different: He'll risk up to 5% of his account on a single trade. Most people would call that crazy, but it works for him because he's honest about what he needs psychologically.

And that brings me to the question that changed everything…

The Million-Dollar Question

During our conversation, he said something that stopped me in my tracks:

“Brian, I don't look at what I want from trading. I look at what hurts me most.”

He went on to explain: “Losing a little money doesn't bother me. What kills me is trading too small. If I'm in a trade with tiny risk and it runs big, I'm sitting there pissed off that I didn't bet bigger.”

This got me thinking about another client – let's call her Sarah.

The High Win Rate Trap

Sarah came to me frustrated beyond belief. She had an 85% win rate but was still losing money overall. When we dug into her system, we discovered the problem:

  • Her winners were small
  • Her rare losses were massive
  • She needed that high win rate psychologically, even though it was mathematically flawed

When I showed her the numbers and suggested a different approach, she made a surprising choice. She decided to stick with her system because she needed that 80-90% win rate to sleep at night. She couldn't handle the emotional stress of being wrong 40-50% of the time.

And you know what? That was the RIGHT decision for her.

The Real Key to Trading Success

Here's what most traders get wrong: They try to force themselves into strategies that don't match their personality. They hear about someone else's success and think they need to trade exactly the same way.

But that's backwards.

The question isn't “What strategy makes the most money?”

The question is: “What hurts you most when trading?”

  • Does losing money keep you up at night?
  • Does trading too small leave you frustrated when winners run?
  • Do you need a high win rate to feel confident?
  • Are you more afraid of missing out than losing money?

Your Trading Must Match Your Psychology

I've seen traders with huge accounts placing $20 trades because losing even that much bothered them. I've seen others risk 3-5% per trade because small wins felt like wasted opportunities.

Neither approach is right or wrong – they're just different.

The magic happens when you build a trading plan that aligns with who you are, not who you think you should be.

Your risk management, strategy selection, position sizing, and even your trading hours should all reflect your genuine psychological makeup. When everything aligns, trading becomes easier, more comfortable, and ultimately more profitable.

Stop Fighting Yourself

Most traders spend years fighting internal conflicts because their trading approach doesn't match their personality. They're constantly sabotaging themselves or feeling stressed about their positions.

Don't be one of them.

Be honest about what truly bothers you most in trading. Then build your entire approach around avoiding that pain while still achieving your financial goals.


Ready to Transform Your Trading?

Tired of it taking SO LONG to actually get consistently profitable? Tired of it being so much harder than it seems like it should be to make profits, consistently and reliably?

Want trading profitably to get easier? Want to get there faster that you've been progressing? WAY faster?

Then check out Profit Assurance™ – the proven method from outside the trading space that gets your trading under control…

  • Without fighting your emotions
  • Without mental hacks or tricks
  • Without having to switch to a new strategy – use whatever you like!

Get the step-by-step framework to build trading confidence, clarity, and control—so you can finally trade without second-guessing yourself.

Click here now to change your trading experience

To your trading success,

Brian McAboy
Inside Out Trading

P.S. Want to talk through what's specifically holding you back in your trading? I'd be happy to jump on a call and help you identify the best path forward. You can book a free strategy session with me at InsideOutTrading.com.