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ChatGPT as My Day Trading Coach: Lessons From My First Trade

3 min readSep 8, 2025

Day trading has always intrigued me as a way to supplement my monthly income. After spending close to 100 hours watching YouTube videos on the Opening Range Breakout (ORB) strategy, I finally decided to take the plunge. Last Friday, I placed my first trade.

I lost money.

But instead of giving up, I decided to treat it as a learning opportunity.

Why I Committed $2,000 to Learning

I know that day trading isn’t about winning every trade. It’s a probability game. To give myself enough room to practice and fail safely, I’ve committed $2,000 as “tuition fees.” That budget will allow me to make 10 trades. At the end of those trades, I’ll decide if I have the skill and temperament to continue as a day trader. This way, I’m testing myself with structure and discipline, not blind hope.

Learning From My First Loss

While losing on my first attempt was disappointing, I’m surprisingly optimistic. The reason? I’ve found an unexpected mentor in ChatGPT.

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After my trade on Open Technologies (ticker: OPEN), I uploaded a screenshot and asked ChatGPT to analyze my entry. My prompt was simple: “Tell me why I made the wrong entry point. The objective is to learn from this

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CW Fong
CW Fong

Written by CW Fong

Retirement Redesigned. Freedom Redefined. Practical paths to early, empowered retirement. eBook: https://tinyurl.com/3crakaut