Never Enough: The Psychology of Money and the Pursuit of Financial Fulfillment

"Never Enough: The Psychology of Money delves into the complex relationship between wealth, happiness, and human behavior. This thought-provoking exploration reveals how our emotions, biases, and societal pressures shape our financial decisions, often leading us to chase an elusive sense of 'enough.' Through insightful stories and psychological research, it uncovers why we struggle to find contentment in our finances and offers a fresh perspective on building a healthier, more fulfilling relationship with money. Perfect for anyone seeking to understand the hidden forces driving their financial choices, this book challenges the notion that more is always better and redefines what true wealth really means."

3/24/20253 min read

John Bogle, the visionary founder of Vanguard who passed away in 2019, once recounted a poignant story about money that forces us to reflect on a critical aspect of wealth. It involves a tale shared by Kurt Vonnegut, where he informs his friend Joseph Heller, the author of the iconic novel Catch-22, that their host—a hedge fund manager—made more money in one single day than Heller earned from his brilliant book throughout its entire lifetime. Heller's reply was remarkable: “Yes, but I have something he will never have... enough.”

That single word, "enough," struck me with its profound simplicity. It made me think about my own life and the wealth I've been fortunate to experience, but more importantly, it illuminated a startling truth: for many in our society, including the wealthy and powerful, the idea of "enough" seems to have blurred beyond recognition.

Let’s dive into two stark examples that illustrate the perils of never feeling satisfied, and the lessons we can glean from them.

Take Rajat Gupta, for instance. Born in Kolkata and orphaned as a teenager, Gupta's beginnings were far from privileged. His journey from the slums to the upper echelons of global business is nothing short of astounding. By his mid-40s, he had risen to become the CEO of McKinsey & Company, the world’s foremost consulting firm. After that, his career flourished—he collaborated with the United Nations, partnered with Bill Gates on philanthropic efforts, and served on the boards of multiple public companies. From a life of unimaginable hardship, Gupta transformed into one of the most successful businessmen on the planet.

But his success brought with it immense wealth. By 2008, Gupta’s net worth reportedly reached $100 million—a staggering amount to most of us. With that kind of money, Gupta could have enjoyed a life of luxury and comfort. Yet, what he aspired for was not just to be a central-millionaire; he longed to join the ranks of billionaires, and his ambition drove him to pursue that goal relentlessly.

During his tenure at Goldman Sachs, Gupta found himself in a world flush with wealth and power among the financial elite. One day in 2008, as Goldman grappled with the impending financial crisis, Warren Buffett made plans to invest $5 billion into the bank to help stabilize it. As a member of Goldman’s board, Gupta learned about this deal before it became public—an invaluable piece of information that could drastically affect stock prices. Within moments of receiving the news, Gupta made a fateful call to hedge fund manager Raj Rajaratnam. What they discussed is not documented, but it’s clear Rajaratnam capitalized immediately, buying shares of Goldman Sachs and reaping a windfall once the deal was made public.

This was just the tip of the iceberg; Gupta’s insider tips allegedly led to $17 million in illicit profits. What seemed like easy money quickly transformed into a nightmare, resulting in both Gupta and Rajaratnam facing prison time, a devastating end to their illustrious careers.

Now consider Bernie Madoff. His name is synonymous with one of history's largest financial frauds, a Ponzi scheme that duped countless investors for over two decades, only to be unveiled shortly after Gupta’s downfall. Yet, what often goes overlooked is that Madoff was more than just a fraudster; he was once a highly successful and legitimate entrepreneur.

In the early 1990s, Madoff operated a market-making firm, matching buyers and sellers of stocks with remarkable efficiency. He built a highly profitable business that, at its peak, executed a staggering volume of stock trades—so effective that he could even pay other brokerage firms to handle their customers' orders, profiting in the process. His legitimate operations generated between $25 million and $50 million yearly.

So, the question lingers: What drove both Gupta and Madoff toward the edge of ethical hell when they had already achieved so much? Their stories remind us of the dangers lurking behind the relentless pursuit of “more” and the importance of recognizing when we’ve truly had enough.