Moving Financial Goalpost

A recent podcast by Morgan Housel, author of The Psychology of Money, explored an interesting idea about the impact of moving goalposts on our financial well-being.

The gist of it was that true wealth isn’t just about earning more—it’s about managing expectations and knowing when to stop chasing. Balancing ambition with gratitude is key to avoiding disappointment and building a meaningful life.

The episode began with a viral tweet featuring a nostalgic photo of a 1950s family standing proudly in front of their modest home. The caption read: “A house, a car, and enough to support a family, all on a Ford factory worker’s wages.” Thousands of comments followed, romanticizing the “good old days.”

But here’s the twist: while life may seem simpler and more content in hindsight, the truth is more complicated. Families in the 1950s typically lived in much smaller homes (around 700 square feet), often lacked health insurance, rarely traveled, and saved little for retirement. These weren’t the glory days of material abundance—they were a time of different expectations.

Today, our relationship with wealth has grown more complex. Despite unprecedented prosperity, many people feel like they’re falling behind. Why? Because envy and ever-rising expectations have reshaped how we define success.

Social media plays a major role. In the past, people compared themselves to neighbors or coworkers. Now, we’re constantly exposed to influencers, celebrities, and strangers living seemingly extravagant lives. This comparison creates a disconnect. We find ourselves asking, “Why don’t I have that?”, even when we’re doing objectively well.

Our economy is excellent at both creating and showcasing wealth—but that visibility can backfire. It feeds a culture where more always feels like the goal, and where comfortable living can feel lacking next to images of luxury and excess.

Morgan Housel illustrates this point with the story of Jesse Livermore, once one of the richest men in the world. Livermore made a fortune during the 1929 stock market crash but later went bankrupt and tragically took his own life in 1940. His downfall wasn’t due to lack of talent—he was one of history’s most skilled traders. But his relentless drive for more became his undoing. If he could double his fortune, why not triple it? If triple, why not quadruple?

Before his death, Livermore wrote:

“I sometimes think that no price is too high for a speculator to pay to learn that which will keep him from getting the swelled head.”

So, what’s the lesson?

Wealth is a two-part equation: what you earn and how you manage your expectations. Many people focus only on the first half. But when our definition of success keeps shifting, we risk never feeling satisfied—no matter how much we achieve.

That doesn’t mean giving up on growth or ambition. Instead, it means being more intentional. Here are three practices to help:

1. Create a goal-based financial plan

   Set clear, personal goals. Prioritize them, anticipate future expenses, and use planning tools to track progress. Align your ambitions with what truly matters.

2. Control your expectations

   You can’t control the economy or markets, but you can control how you measure success. Avoid letting external comparisons dictate your sense of worth.

3. Know when to stop

   Sometimes, the smartest financial move is saying no—to the bigger house, nicer car, or higher-paying role. Saying no to “more” can mean saying yes to what truly matters.

The modern paradox is this: despite historic levels of prosperity, many feel unfulfilled. The answer may not lie in chasing more, but in redefining what “enough” means.

True wealth may come not just from success, but from recognizing when it’s time to stop chasing—and start appreciating.