Improving Investor Behavior: When investing starts to look like gambling
May 17, 2026
Not long ago, gambling largely remained in places designed for gambling. You drove to Las Vegas, bought a lottery ticket at a gas station, or filled out a March Madness bracket with friends or coworkers. Boundaries, both physical and emotional, existed to separate gambling from the rest of daily life.
Today, those boundaries are fading. Sports betting occurs on phones. Prediction markets allow people to wager on elections, economic data and world events. Cryptocurrency speculation, meme stocks, leveraged options and online trading platforms all compete for the same thing: attention, excitement and the possibility of a fast win. What was once called gambling is now marketed by some as “investing.”

While greed is one motivating factor, I’ve often found another emotion equally to blame: anxiety.
A recent study from Northwestern Mutual found that nearly 40% of Americans are either investing in or considering high-risk speculative activities such as cryptocurrencies, options trading, meme stocks, sports betting or prediction markets. Among them, nearly three-quarters reported doing so because they feel financially behind and believe these approaches may help them catch up faster. Among Gen Z investors considering speculative investments, roughly 80% said they feel pressure to accelerate wealth-building quickly.
That may be the most important point in this entire article. At its core, accumulating wealth requires two things: growth and time. Given years to compound, annual returns can be much smaller while producing the same (or a greater) long-term result. But the opposite is also true: The shorter the runway, the higher the gains must be to compensate for lost time. As a result, many people aren’t trying to build wealth but to compress time. And that’s when financial mistakes often follow.
Warren Buffett once said the stock market is a mechanism for transferring money from the impatient to the patient. That feels especially relevant today because modern financial media culture increasingly rewards emotional intensity over discipline. Slow accumulation feels boring. Consistency feels inadequate. Compounding feels too slow for people who believe they’re already behind.
But here’s an important distinction worth making: Feeling behind and actually being behind are not always the same thing.
Some people truly are behind. Perhaps they started saving late, had financial setbacks, raised families, cared for aging parents, lost jobs or simply reached their late 50s or early 60s with insufficient savings. For them, the anxiety is real. Retirement no longer feels distant, and the numbers may not support their desired life.
Others may do well but feel behind because comparison has become constant. Social media shows only the highlight reel: the early retiree, crypto millionaire, friend on vacation or stranger claiming to have turned a few thousand dollars into a fortune. When everyone else appears to be winning quickly, ordinary progress can feel like failure.
Both groups can arrive at the same dangerous conclusion: “I need bigger returns.”
The problem is that bigger returns usually require bigger risks. These outsized risks are then shouldered by those who can least afford them.
Imagine a 62-year-old with $400,000 saved for retirement. They may feel they need a dramatic return to catch up, making an investment that could double quickly seem powerfully appealing. But if that same investment gets cut in half, the damage isn’t solely psychological; it could permanently alter their retirement. With less time to recover and fewer working years or opportunities left, it’s harder to rebuild from a major mistake.
This is where investing and gambling fundamentally diverge. Investing is built around ownership of productive assets over long time periods. Gambling is built around short-term outcomes and probability. One depends on endurance, the other on timing and luck. One quietly compounds, while the other creates emotional spikes of hope and disappointment.
Yet today those distinctions are increasingly blurred.
Sports betting provides a clear example. Gambling used to involve friction. You had to go somewhere, make a deliberate decision and participate consciously. Now, betting can happen from the same device used to check the weather or text your children. During broadcasts, odds are discussed as casually as player statistics, and entire business models depend on normalizing constant speculation.
Prediction markets take this even further by converting almost every event into something “tradable.” Elections, inflation data, Federal Reserve decisions and geopolitical events become opportunities to “make a call.” This creates the illusion that intelligence and prediction are the primary drivers of wealth creation.
History suggests otherwise.
The great American fortunes were rarely built suddenly. Most accumulated quietly through long-term ownership of productive businesses combined with disciplined behavior over many years. An investor who saves consistently, owns diversified productive assets and allows time to work may never experience the thrill of an overnight win. But they also avoid the devastation following an oversized bet gone wrong.
Here’s the biggest takeaway: The answer to being behind is not swinging harder.
Instead, become more intentional. Spend less than you earn. Save consistently. Extend your time horizon emotionally, even if your calendar horizon feels shorter. Own productive assets. Control behavior. And, perhaps most importantly, reject the idea that everyone else is getting rich quickly.
Most are not.
The tragedy of modern speculation is not simply that people lose money. It’s that speculation often targets the very people who feel most pressured to recover quickly. It convinces them that slow progress is failure, when it’s often exactly what successful investing looks like.
As Morgan Housel wisely observed, the critical question is not, “What is the highest return I can achieve?” It is, “What return can I sustain for the longest period of time?”
The desire to improve your financial life is understandable. The danger comes when impatience turns desire into a wager. Real wealth is rarely built by compressing time. More often, it’s built by respecting it.
Steve Booren is the founder of Prosperion Financial Advisors in Greenwood Village. He is the author of “Blind Spots: The Mental Mistakes Investors Make” and “Intelligent Investing: Your Guide to a Growing Retirement Income” He was named by Forbes as a 2024 Best-in-State Wealth Advisor, and a Barron’s 2024 Top Advisor by State.
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