{"id":871,"date":"2026-09-30T11:00:00","date_gmt":"2026-09-30T11:00:00","guid":{"rendered":"https:\/\/www.cahabawealth.com\/insights\/?p=871"},"modified":"2026-09-30T10:16:31","modified_gmt":"2026-09-30T15:16:31","slug":"why-trying-less-hard-sometimes-works-better","status":"publish","type":"post","link":"https:\/\/www.cahabawealth.com\/insights\/2026\/09\/30\/why-trying-less-hard-sometimes-works-better\/","title":{"rendered":"Why Trying Less Hard Sometimes Works Better"},"content":{"rendered":"\n

Insights by Dr. Daniel Crosby | Cahaba Commentary by Brian O\u2019Neill, CFP\u00ae<\/p>\n\n\n\n

9\/2026<\/p>\n\n\n\n

\n\n\n\n

A Note from Brian:<\/strong><\/em> I am thrilled to share the first in Cahaba\u2019s new series of articles that shed light on human behavior and how that shapes decision-making in our financial lives. We will lean heavily on the works of Dr. Daniel Crosby, an incredibly talented writer and thought leader who spends his time in the field of behavioral finance. I\u2019m also pleased to call Daniel a friend. Our focus in sharing these with you is to help take a step out of the nuts and bolts of finances (think numbers) and into the thoughts and decisions that ultimately shape each individual\u2019s financial future. In my now 30 years in this business, I have found it is these decisions that are most important in creating positive – and unfortunately more often than we hope \u2013 negative financial outcomes. In this first article, Daniel delves into the benefits of trying less hard.<\/p>\n\n\n\n

I relate to this article most when I’m lying in bed at night and can\u2019t fall asleep. As a noted napper, I can doze on the sofa on command, but get to actual bedtime, sleep often evades me. I\u2019m trying too hard! The parts of this note that resonate the most involve the \u201cchecking on the markets regularly\u201d section. While possibly an urban legend in our industry, a rumored internal study by Fidelity claimed that the best-performing investment accounts belonged to people who had died or forgotten their login details. I have seen this time and again, and while difficult to fight, I often remind my clients to tuck those statements in a drawer, and remember it\u2019s a marathon, not a sprint. I hope you enjoy this series!<\/p>\n\n\n\n

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Why Trying Less Hard Sometimes Works Better<\/h2>\n\n\n\n

Navy SEAL training includes a notorious exercise called “drownproofing.” Trainees are placed in a deep pool with their hands tied behind their backs and their feet bound together. Their task is to survive in the water for five minutes. The exercise sounds like a recipe for panic, and for most untrained people it would be exactly that.<\/p>\n\n\n\n

The trick to drownproofing is counterintuitive. Trainees are taught to relax, sink slowly to the bottom of the pool, and then push off the floor to rise back to the surface for a quick breath of air, before sinking and repeating the cycle. The exercise rewards calm and rhythmic surrender. It punishes the natural instinct to thrash, struggle, and fight the water.<\/p>\n\n\n\n

The British philosopher Alan Watts called this principle “the backwards law.” As he put it, “When you try to stay on the surface of the water, you sink. But when you try to sink, you float.” Sometimes the harder we work at something, the more reliably it eludes us.<\/p>\n\n\n\n

This applies more often than we tend to admit, and it shows up clearly in financial life.<\/p>\n\n\n\n

Consider a useful insight from the brain itself. Pareidolia is the well-documented human tendency to find meaningful patterns in ambiguous stimuli. It is why we see faces in electrical outlets, animals in clouds, and figures in slices of toast. The brain does this automatically. We are not deciding to find patterns. We are wired to find them whether we want to or not.<\/p>\n\n\n\n

The same wiring applies to meaning more broadly. We are meaning-seeking creatures by default. When meaning seems absent from our lives, the issue is rarely that we are not trying hard enough. More often, the issue is that we are trying too hard and in the wrong direction.<\/p>\n\n\n\n

Viktor Frankl, the Austrian psychiatrist whose work survived the Nazi concentration camps and shaped much of modern psychology, captured this principle in Man’s Search for Meaning. “Don’t aim at success. The more you aim at it and make it a target, the more you are going to miss it. For success, like happiness, cannot be pursued. It must ensue, and it only does so as the unintended side effect of one’s personal dedication to a cause greater than oneself.”<\/p>\n\n\n\n

The economist Charles Goodhart formulated a related principle, now widely known as Goodhart’s Law. “When a measure becomes a target, it ceases to be a good measure.” Two historical episodes illustrate the point unforgettably. In 1902, French colonial authorities in Hanoi tried to control bubonic plague by paying citizens for every rat tail they brought in. Locals quickly figured out that breeding rats was more profitable than killing them, and the rat population exploded. A similar policy in colonial India offered bounties for dead cobras. When citizens began breeding cobras to collect the reward, authorities ended the program, only to find the streets more full of cobras than ever. The phenomenon is now called the Cobra Effect.<\/p>\n\n\n\n

The same dynamic surfaces in financial planning more often than most people realize.<\/p>\n\n\n\n

The investor who checks their portfolio every morning, hunting for evidence of progress, often makes worse decisions than the investor who reviews quarterly. The household that aggressively tracks every dollar of every category in every spending app sometimes ends up more anxious about money than the household that simply automates the savings rate and lets the rest unfold. The professional who optimizes every career move for maximum compensation often discovers, fifteen years in, that the optimization itself produced a life nobody actually wanted to live. The retiree who relentlessly counts how much joy they should be having, given how much money they have saved, frequently fails to actually experience joy at all.<\/p>\n\n\n\n

In each case, the relentless measurement becomes the obstacle to the very thing being measured.<\/p>\n\n\n\n

The healthier alternative is to build a financial structure that runs without your constant attention, then turn your attention to actually living. Automate the contributions. Choose the broadly diversified portfolio. Set the review schedule and honor it. Then, in the meantime, lose yourself in the work, the people, and the pursuits that actually matter. Meaning, like the Navy SEAL trainee in the pool, tends to surface when we stop fighting so hard for it.<\/p>\n\n\n\n

The point is not to care less about your financial life. It is to care more about what your financial life is actually for, and to trust that a sound structure, properly designed, will hold while you do.<\/p>\n\n\n\n

This week’s challenge: Identify one financial number you check more often than is useful, commit to a less frequent review schedule for the next month, and redirect that recovered attention toward something that actually deserves it.<\/em><\/strong><\/p>\n\n\n\n

<\/p>\n","protected":false},"excerpt":{"rendered":"

Insights by Dr. Daniel Crosby | Cahaba Commentary by Brian O\u2019Neill, CFP\u00ae 9\/2026 A Note from Brian: I am thrilled to share the first in Cahaba\u2019s new series of articles that shed light on human behavior and how that shapes decision-making in our financial lives. 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