Imagine if you had invested S$100,000, the bulk of your savings, into the Straits Times Index (SGX: ^STI) when it reached a peak of 5,041 on 23 February 2026. Less than a month later, the index fell to 4,697 (down almost 7%) on 9 March 2026. Your portfolio is suddenly worth less than what you paid. Many investors fear this, making them wary of investing in a bull market.

Why Investing at the Peak Feels So Painful

Investors tend to feel the pain of losses more intensely than the satisfaction of equivalent gains due to loss aversion. A S$100 loss stings more than an equivalent S$100 gain pleases. Investors are tempted to sell when they see losses, fearing further declines and regretting that they did not wait for lower prices.

Was It Really a Mistake?

Remember, nobody can consistently predict market peaks. Professionals also struggle to time markets consistently, and “best” timings are only obvious in hindsight. However, history suggests markets eventually recover....