In this episode, we dig into one of the most persistent investing dilemmas: knowing when the “right time” to invest actually is. Through personal stories and historical examples, we explore why the market always feels risky in the present—even though the biggest long-term gains often come to those who invested during turbulent times. The message is simple but powerful: the best time to invest is when you have the money, not when the market feels calm.

Key Takeaways

• It always feels like a risky time to invest, while simultaneously feeling like the past was a better, safer time to invest. The irony being that the past also felt risky when it was the present.
• History shows that even the “worst” times often lead to strong long-term growth.
• Waiting until it feels safe to invest usually means missing out—the feeling of uncertainty never fully goes away.
• Invest when you have the money, not when the headlines are favorable.
• You can reduce stress by investing gradually (e.g., monthly contributions), balancing risk through diversified investments, and choosing investments that you can own for a long, long time.

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