Q&A: The Goalposts Moved — Is That Actually a Problem?

#718: What happens when the financial strategy that once felt obvious suddenly becomes a lot more complicated?
Les is approaching financial independence but has realized there’s one thing missing from the traditional FIRE equation: how do you continue meaningful charitable giving after you stop earning a paycheck?
Jaime has built a sizable retirement portfolio, but now he’s wondering whether the complexity inside his 401(k) actually matters—or if he’s overthinking the mechanics of retirement accounts and Roth conversions.
Tina has owned a successful rental property near the University of Central Florida for more than a decade, but changing market conditions and growing competition from corporate landlords are making them wonder whether it’s finally time to sell.
We’re diving into all of that today, so let’s get started.
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