In an age of curated social media feeds, even our most enriching experiences are vulnerable to comparison. We’ve long been told that spending on experiences, especially with loved ones, offers the best return on investment. But as Morningstar’s Christine Benz posits in a recent conversation with financial advisor Carl Richards, what happens when those experiences are constantly weighed and measured against the seemingly perfect lives of others?
Richards, the author of *Your Money: Reimagining Wealth in 101 Simple Sketches* and a guest on *The Long View* podcast, argues that this constant comparison is a "huge problem," one that cheapens our joy and distracts us from what truly matters. The solution, he suggests, is not to unplug completely, but to engage in a more intentional, deeply human conversation with ourselves about our values. His blueprint for a richer life is built on a simple yet profound premise: stop doing what you think you *should* do, and start discovering what you actually *want* to do.
The first step is to recognize the subtle tyranny of the "shoulds." Richards shares a telling anecdote from author Gretchen Rubin, who was repeatedly pressured at a party to take up skiing. The woman, insisting, eventually had a moment of clarity, admitting, "I don't like skiing either. I've just been doing it because it was what you do." This story, Richards notes, is a powerful illustration of a common trap. He and his wife fell into it themselves, scheduling "dinner and a movie" with friends to build connection, only to realize the noisy restaurant and dark theater were antithetical to their goal. Their true desire was for the collaborative, conversational act of cooking a meal together—a discovery that was not only more fulfilling but also less expensive. The path to contentment begins when we dare to question the default script.
But how do we find our personal script? Richards’ answer is a bias toward action: run small, low-cost experiments. Instead of dreaming about a $5 million sailboat, first go for a sail. Instead of assuming you love luxury cars because you can afford one, do what financial writer Morgan Housel does: rent a Porsche for a weekend. Housel finds that before he even leaves the lot, he’s learned a valuable lesson for a fraction of the price: he admires the craftsmanship but doesn't need the car. This experimental approach applies to defining "enough," which Richards insists cannot be a static number. It’s a feeling you discover through practice, whether it’s a "no-spend month" to test your needs or a "staycation" to see if a simpler vacation brings more joy.
Perhaps the most poignant application of this practice is for retirees. Richards observes a fascinating paradox: the very habits of delayed gratification and frugality that lead to financial success become a major barrier to enjoying it in later years. These individuals have spent a lifetime saving and now find themselves at the finish line, unwilling to give themselves permission to spend. The research on "funded contentment" is clear, but old habits die hard
The solution, once again, is to practice. Richards offers a surprisingly simple prescription: "Tomorrow, I want you to find something small that you’ve always just wanted." It could be a $12 latte from your favorite coffee shop. The point isn't the purchase; it's the "$12 rep"—a small, deliberate act to rewire the brain and experience the joy of spending without guilt. This small practice can build the confidence to make larger, more meaningful expenditures, like funding a grandchild’s sailing camp or creating a scholarship for aspiring engineers. It’s about transforming a lifetime of saving into a legacy of intentional giving and living.
Ultimately, Carl Richards’ advice is a call to re-imagine wealth not as a number in a bank account, but as a tool for crafting a life that aligns with your most authentic self. By breaking free from the comparison trap, embracing the power of small experiments, and practicing the art of spending, we can move beyond simply accumulating money to using it in ways that bring genuine, lasting fulfillment.