If You Prefer to Pick Stocks
Author Prompt, ChatGPT
You’ve done the research. You’ve watched the sector. Maybe you follow someone you trust, maybe you built the thesis yourself. Either way, when it works, you earned that. Go ahead and own it.
Stock picking gives you something systematic investing genuinely cannot: great stories. You can sit across from someone and say exactly what you bought, exactly why, and what happened, good or bad. That story belongs to you. So does the identity. You are someone who takes this seriously, who does the work. I have no interest in talking you out of it.
I can relate. I loved my investment stories. I held that identity for decades.
Then came 2003.
S&P Daily Price Chart for 2023, Source: stockcharts.com
I had been sitting on a large short index ETF for months already convinced the market still hadn’t found its real bottom yet. The thesis seemed tight and the analysis said wait. So I waited. While the market kept climbing in 2003, I held on through part conviction, part stubbornness, and probably some hope dressed up as research. You may know the feeling: the market moving against you, the position bleeding, and the internal voice saying “the analysis is still right, just give it more time.” That specific dread, that refusal to let go, cost me in ways that went well beyond the dollar amount.
The loss itself hurt less than what came later: recognizing what had actually driven the decision. The fear of being wrong and a need to prove I was smarter than the market had taken over the original logic for the position. I didn’t have rules. I had a thesis and conviction.
That experience pushed me toward wanting a more professional approach to the markets. I found Van Tharp’s work on systems and position sizing. He laid out a framework for thinking about investing through rules and repeatable processes rather than trying to argue with the market about who was right. That shift took time but it had started.
Stock picking asks you to be good and right. A systematic approach asks you to follow a process. Both can produce results. Last year gave me a clean look at both approaches running side by side.
Daily Gold Price Chart, July - December 2025. Source: stockcharts.com
Gold made a significant move up in the second half. I held positions in two different accounts simultaneously. One came from my own read: the long technical setup and the fundamentals. I studied both and opened a gold miner position. The other came later through the SmartSignal System. The system saw what the rules required and said to enter when conditions were met. No narrative needed.
Same asset class. Similar moves. Very different experience.
The first trade felt earned. The systematic trade felt mechanical. I didn't have to second-guess the entry or check the chart for confirmation. The simple rules said what to do.
Rules changed my own investing too: risk, entries, and exits. Some fear and hope still show up but they don't run the show anymore.
Ever investor carries some fear and hope into their decisions. The question is how much you let them drive.
Structure and a systematic approach change the equation. The more rules govern your decisions, the less emotions get a vote. That matters at any age. But as retirement gets closer, a bad pick costs you time and you no longer have the time to recover.
Pick stocks if that's your game. Add structure where you can. The closer you get to retirement, the more that structure protects everything you've built.
***
Want more guidance like this? The Growth Guardian Investor newsletter is free and built for self-directed investors approaching retirement.
Important Disclosures
This article is for educational purposes only and does not constitute investment advice or a recommendation to buy or sell any security. Investing involves substantial risk, and past performance does not guarantee future results. Mentions of any system or methodology are illustrative, not advisory.
Full Disclaimers Statement on www.gginvestor.com.