The Charitable Assumption: A Better Default for Managing Money and Relationships

This article appears as part of Casey Weade's Weekend Reading for Retirees series. Every Friday, Casey highlights four hand-picked articles on trending retirement topics and delivers them straight to your email inbox. Get on the list here.
Weekend reading the charitable assumption Weekend reading the charitable assumption

Weekend Reading

We’ve all made snap judgments—about strangers, loved ones, even ourselves—without knowing the full story. This article invites us to pause, breathe, and reconsider.

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Here, author Tim Maurer introduces the concept of charitable assumption: choosing to believe the best about others, especially when they’re not at their best. This simple shift in mindset can transform how you handle money and relationships, especially in retirement—when family dynamics, financial decisions, and deep-seated money scripts often collide. Here’s how to put it into practice:

📌 Give Yourself Grace: Financial missteps are inevitable. Understanding your "money scripts"—those deep-rooted beliefs formed early in life—can turn guilt into growth.

📌 Rediscover Empathy with Your Partner: Honest conversations about money memories can heal misunderstandings and revive connection

📌 Replace Comparison with Curiosity: Whether it's a neighbor's lavish vacation or a friend’s spending habits, resist the urge to judge. Assume there’s more to the story.

Key Takeaway: You will find that the beauty in charity lies in the fact that it doesn’t require wealth. In retirement and beyond, this practice might just be the most enriching investment you make.