Penny Wise, Pound Foolish: A Small Investing Mistake That Taught Me a Bigger Lesson
“Penny wise, pound foolish” is a phrase I have heard since I was young, usually used to describe people who focus too much on small savings while missing the bigger picture. Over time, I have realised that this saying applies surprisingly well to investing, and more uncomfortably, to my own behaviour as an investor. There have been many occasions where I wanted to buy a particular share, but instead of relying on valuation, fundamentals, or any form of structured analysis, I fixated on a price that simply felt right. That number was not derived from spreadsheets or charts. It was just a number that I felt nice to own the stock at, such as whole numbers or seemingly auspicious numbers ending with '8', and I told myself I would only buy if the price came down to that level. If I am lucky, sometimes it did. When it did, I felt delusionally clever, disciplined, and patient. It reinforced the belief that waiting was the right thing to do. However more of...