Harken back to the good old days. There were no smartphones to distract us, work was confined to the office from 9 to 5, and politics were less heated. Of course, that's looking back with quite the rose-tinted spectacles. In reality, technology has given us more free time, work flexibility has increased significantly over the past decade, and engaging in domestic social and political movements could have been downright deadly in the 1960s.

It’s natural for us to long for what is familiar and shy away from new perceived risks—even when we know there could be something better than the stale status quo. Years ago, a small German community faced a unique chance to reinvent itself. Located atop a lucrative mineral deposit that its government elected to tap, the physical town was slated for demolition. The upside was that the community could redesign a new village from scratch, entirely funded by the German government. Presented with unlimited possibilities, including ditching what irked people and installing new modern amenities, the townspeople chose to replicate their old, flawed, winding hamlet exactly. They decided to play it safe, opting for the familiar.

Every red-blooded American surely embraces the “no guts, no glory” maxim, but we, too, occasionally defer the chance for a better life—at least in a small way—due to fear. Those instincts are on full display in financial markets. While there are some natural gamblers, most people prefer to play it safe with their portfolio. It’s known as conservatism—a cognitive bias that causes us to be overly prudent and resistant to change. To wit, investors commonly hold onto losing stocks for too long and avoid updating their portfolios due to inertia.

Psychologically, we are wired for predictability, even when predictability might harm us. One study found that daughters of alcoholics were more than twice as likely to marry an alcoholic than daughters of nonalcoholics because even painful familiarity feels safer than a different (better) life.1 Research also reveals that people dislike uncertainty so much that they prefer receiving bad news than facing uncertainty—we'd rather get a negative diagnosis than sit for hours alone in the waiting room.2

Such conservatism can wreak havoc on your net worth, particularly regarding market volatility and market timing. Even novice investors understand that stuffing money under the proverbial mattress is a surefire way to never hit financial goals, but too often, individuals remain cash, perhaps from rolling over an old 401(k) or receiving a significant inheritance. Some folks just never get around to reinvesting due to inertia, while others are afraid to risk buying right before a market decline. The warm blanket of cash is comforting in the moment but prevents you from keeping up with inflation.

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On market timing, specifically, I’m going to offer a twist on the usual advice of “just don’t do it.” Yes, reinventing your portfolio on a whim (selling a diversified allocation and going to cash) is almost always a bad decision, but once in cash, you then face a new dilemma: stay out of the market or get back. It’s this second conundrum that has destroyed many market-timers' wealth. At the time you sell, you have convinced yourself that you will reinvest when volatility calms down or once stocks really crash. Those plans usually fall apart since stocks discount the news—they bottom and then rally on worsening economic conditions. Either the market falls (in which case you are too afraid to re-enter), or a rally ensues, and you avoid buying at prices above where you sold. 

So, it’s the second decision—the getting back in—which is so hard. As the infamous investor Jesse Livermore quipped, “The stock market is never obvious. It is designed to fool most of the people, most of the time.” By playing it safe—avoiding volatility by exiting a well-crafted portfolio—investors inadvertently jeopardize their long-term financial security.

Breaking free from conservatism's shackles is no easy task, but the following strategies can keep you from being overly cautious:

Conduct a Pre-Morten
Think about what could go wrong with hanging out in cash for too long. A market rally may relegate you to the sidelines forever if you refuse to reinvest at higher prices. Conversely, if stocks crash, do you think you have the prescience and fortitude to buy at the lows? The honest answer generally is no. By quickly considering adverse outcomes, you may find you’re better off being invested.

Embrace Risk
Accepting market risk can be essential if you want to earn decent returns. In a very real sense, volatility and uncertainty are the cover charge for entrance into the greatest wealth-creation machine on Earth, the capital markets. 

Automate. Automate. Automate.
Routine investing and structured rebalancing can help keep your financial plan on track. Automation dampens the impact of emotions, which is always helpful. Additionally, pre-commit yourself to regular portfolio meetings with your advisor so you can review your allocations no matter the market conditions.

The Bottom Line
Playing it safe in markets can be dangerous. While the familiar may be comforting, conservatism, in some circumstances, may often prove to be the most significant risk of all. For some, staying invested is key, and reaching financial goals can demand thoughtful risk-taking and intentional, disciplined action.

 

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1Schuckit MA, Tipp JE, Kelner E. Are daughters of alcoholics more likely to marry alcoholics? Am J Drug Alcohol Abuse. 1994;20(2):237-45. doi: 10.3109/00952999409106784. PMID: 8042605.

2Jesper Fischer Ehmsen et al., Thermosensory predictive coding underpins an illusion of pain.Sci. Adv.11,eadq0261(2025).DOI:10.1126/sciadv.adq0261
Orion Behavioral Finance ("Orion BeFi") is the branding name of various tools and services related to behavioral finance offered by Orion Advisor Solutions, Inc. and its subsidiaries. Orion BeFi tools are crafted to help investors and their financial advisors integrate behavioral psychology research into their investment decisions. Orion BeFi tools and services do not provide investment advice.