3 Money Decisions You’ll Either Regret Forever… or Be Glad You Made

Three questions. No overthinking. Just real answers. This week, we’re tackling three financial decisions that feel simple on the surface… but can completely change the direction of your life. Do you walk away from a once-in-a-lifetime real estate deal—or risk blowing up your early retirement plan to take it? How do you get a $25,000 raise and still feel broke? And before you get married… do you combine finances, or protect your independence? These aren’t spreadsheet decisions. They’re life decisions. And the tricky part? Smart people land on both sides of every one of them. So we’re speed-running each scenario—what matters, what doesn’t, and how to think about these moments when there’s no obvious “right” answer. Because sometimes the biggest financial mistake… is thinking there’s only one way to do it.

You can listen to 3 Money Decisions You’ll Either Regret Forever… or Be Glad You Made online on Radio and Podcast. Open the player on this page to stream the available audio.

3 Money Decisions You’ll Either Regret Forever… or Be Glad You Made is an episode from Million Dollar Plan by IBJ Media.

This episode is 67:26 long.

This episode was published on May 1, 2026.

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