Stephen Covey, the author of The 7 Habits of Highly Effective People, tells a story that’s as instructive as it is unsettling. On a New York subway, he noticed a man sitting quietly while his children wreaked havoc. Covey finally said, “Sir, your children are really disturbing a lot of people.”
The man replied, “You’re right. We just came from the hospital where their mother died about an hour ago.”
Are you making the charitable assumption?
I share that feeling that likely just churned in your gut—because, if you’re anything like me, you may have rarely corrected a parent for their apparent mismanagement of an unruly child, but you sure have turned around conspicuously, glared, or even mustered up a hopefully anonymous “Shhhh!”
Now please forgive yourself, because this is a well-documented tendency dubbed the fundamental attribution error, where we default to excusing our own mistakes by attributing them to external factors—while judging others’ mistakes as reflections of their lacking character. Eeesh.
The point, of course, is that we rarely don’t know the story behind the story—and this blind spot makes us vulnerable to the mismanagement of our relationships, and especially our relationships where money is involved.
Fortunately, we’re offered an antidote to this poisonous bias, and I’ll offer three practices that we can apply to retrain our hearts and minds that I hope will reduce your stress in life and lead to more effective money management.
Antidote—The Charitable Assumption
While this particular antidote has been discussed by philosophers and theologians for millennia, I learned this new phrase from the best-selling book, Unreasonable Hospitality, written by the world’s top restauranteur, Will Guidara.
Guidara was half of the guiding force, along with Chef Daniel Humm, that led Eleven Madison Park to become known as the best restaurant in the world by The World’s 50 Best Restaurants. Part of their success, however, was Guidara’s insistence that they not replicate the hostile work environment for which the restaurant business has become notorious. (See The Bear.)
They developed a code that cultivated a cultish culture among the employees, helping EMP reach such lofty heights, and one of the core components is the charitable assumption, which Guidara defines simply as “a reminder to assume the best of people, even when (or perhaps especially when) they weren’t behaving particularly well.”
As you might imagine, they only hire the best-of-the-best culinary and service staff at the world’s best restaurant, so if one of those exceptional servers was late, unusually inhospitable, or underperforming, the charitable assumption insisted that there must be something circumstantial—not character-driven—that led to the anomalous behavior.
Therefore, the question to said employee would be, “Hey, is everything ok?” not “What’s wrong with you??” or worse yet, the gossipy, “Can you believe they just did that?” which tends to fester like a disease, whether in an organization or a household.
3 Charitable Assumption Practices
Speaking of household, let’s turn our attention to three practices that can help us apply the charitable assumption in our lives, loves, homes, and finances:
1. Be Charitable To Yourself
I think it’s important to start with ourselves, because often times our tendency to blame others is actually rooted in self-flagellation. Eckhart Tolle says, “Anything that you resent and strongly react to in another is also in you.” And as much as I want to argue with this quote, I think he’s on to something.
It’s exceedingly difficult to show grace to others when we can’t—or won’t—show it to ourselves. Fortunately, the management of our personal finances is ripe territory for learning this lesson—because it’s not likely that a year, month, or even a week will expire without you making a financial mistake.
In fact, money management is more an exercise in mistake management than an unachievable perfection—partly because the complexity of money today makes it virtually impossible to catch everything in real-time, and partly because there is much that is beyond our control…and even more that is beyond our consciousness.
Carl Jung said, “Until you make the unconscious conscious, it will direct your life and you will call it fate.” We’ve learned that much of what we do with money in adulthood is based on formative hard-wiring we endured before the age of 10.
The financial advisor / psychotherapist trio of Rick Kahler, Ted Klontz, and Brad Klontz gave this phenomenon a helpful moniker—money scripts. These are often more feelings than thoughts that guide our behavior when we react to whatever stimuli we face.
That wince you feel when your friend asks if you want to split the bill even though they racked up the apps and drinks while you were careful? The way you respond to a homeless person asking for money? The pride you feel when sporting a Louis Vuitton purse? These instantaneous responses are all money scripts. And it is through their exploration that we can identify, articulate, and, if desired, change them.
Exploring our money scripts helps us extend a charitable assumption inward—to understand our own choices with compassion rather than criticism.
2. Be charitable to your spouse.
If you want to live dangerously, talk to your spouse or partner about money. If you want to seriously risk your marriage, don’t.
Money mismanagement mangles marriages. And you already know why—because we often don’t even know our own money scripts, much less our spouse’s—so this becomes ground zero for the financial misapplication of the fundamental attribution error.
If you want a crash course, check out the funnily named book, The Financial Wisdom of Ebeneezer Scrooge, a short collaboration of the trio mentioned previously, and please don’t wait until the holidays to do it.
But you don’t have to learn anything else to be a student of your spouse. You used to grant them the charitable assumption—remember? Once infatuation set in in, early in your dating, no matter what story they told about their past, present, or aspirations for the future, they seemed somehow infallible.
You can do it again. Set 60-90 minutes aside—without those rambunctious kids around and with your favorite deliberative beverage—and tell your personal money stories to one another. Without judgement, listen and share, the most indelible memories you have of money growing up. Before the end of this exchange, you should begin to see your partner not as the miser or spendthrift you’ve come to label them, but as the collection of a lifetime of experiences and circumstances that have shaped them.
If you want a template, my wife, Mika, and I recently had one of these conversations—unscripted and on camera—not because we are marriage experts, but simply because we were willing. I hope you find it helpful.
And if you want an even simpler start, simply ask your spouse, “What’s one of your earliest memories about money?” And then listen curiously, not critically.
3. Be charitable to your friends…and your “friends.”
OK, I’ve saved the hardest for last—because I know that even though you hit the like button, or even commented with a cute emoji, when your neighborhood acquaintance sent a slew of pictures from their recent trip to Ibiza, you were actually thinking, “They can’t really afford that!”
And maybe they can’t. Maybe they can’t afford their house(s) or car(s) either—but maybe they can. Or maybe they’re the person who just went through a tragic season in life and spent their life savings to splurge on a soul-filling adventure to remind themselves that there is beauty in the world.
The soul-sucking danger of comparison is alive and well in 2025, and it really doesn’t hurt whomever we’re judging at all—it only hurts us.
So, here’s an idea: Let’s try curiosity over condemnation.
The Best Part About Charity
The best part about charity is that it doesn’t actually require financial wealth. We tend to equate charity, generosity, and philanthropy as the sole domain of the ultra-wealthy. But my favorite author of all time—C. S. Lewis—offers us a simpler, more potent view of the virtue of charity:
“Charity means love,” Lewis says, but love “does not mean an emotion. It is a state not of the feelings but of the will; that state of the will which we have naturally about ourselves, and must learn to have about other people.”
Of course, many of us never learn what Lewis insists we must. And I submit that no matter how rich, our lives are poorer for it. In those moments when we wallow in self-pity, blame those closest to us, or judge those with whom we interact, we turn what could be a lesson learned, a relationship deepened, or a curiosity satisfied into little more than the false god of self-righteousness—or worse yet, a general mistrust of everything and everyone (which social media and the news are happy to profitably stoke).
On the other hand, the generous assumption isn’t just a mindset, it’s a multiplier of trust. It softens our inner critic, strengthens our closest relationships, and builds bridges where money so often builds walls.