I’ve been focused on building passive income since 1999, back when I had to be in the office by 5:30 a.m. and often worked past 7 p.m. every night. Weekends were another eight hours or so. I knew I couldn’t sustain a traditional 40-year career working those kinds of hours, so I began saving and investing aggressively to break free by 40.

Now I’m focused again on building enough passive income to fully cover our family’s desired living expenses by December 31, 2027. And I’ve been reminded of an ongoing battle: the trade-off between generating risk-free passive income versus taking risk to earn higher potential returns.

As I’ve gotten older, I’ve become more risk-averse, partly because the dollar amounts at stake have grown.

Losing $20,000 on a $100,000 portfolio feels like a kick in the shins. But watching $1 million evaporate from a $5 million portfolio? That hits like you