Never Enough Syndrome (3 Min Read) | Vol. 175

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October 31, 2025

“He who knows that enough is enough will always have enough.” – Lao Tzu

Never Enough Syndrome 

The recipe for a life of discontent is equal parts ambition, drive, and an ambiguous definition of success. 

Authors Kurt Vonnegut and Joseph Heller once attended a party thrown by a billionaire on Shelter Island in New York. Vonnegut teased Heller that the billionaire earned more in a single day than Heller would ever make from his best-selling book, Catch-22. Heller’s retort has since become legendary.

“Yes, but I have something he will never have … enough.”

The billionaire in question was John C. Bogle, founder of the Vanguard Mutual Fund Group. This exchange reportedly inspired him to write a whole book on the topic, Enough: True Measures of Money, Business and Life.

My guest on this week’s podcast, Sahil Bloom, changed the trajectory of his life by getting clear on what success meant for him. In his book, The Five Types of Wealth, Bloom retells the Heller story and dives deeper into what I’ll call the “Never Enough Syndrome.” In a 2018 paper published by Harvard Business School, professor Michael Norton found that millionaires at every wealth level say they’d need “two to three times as much” to achieve perfect happiness.

Absent a clear personal understanding of success, no amount of money is enough. The more you acquire, the more you desire. 

The scary thing is that “Never Enough Syndrome” isn’t just about money. It applies to any external measure of success – wealth, awards, titles, possessions, territory, or power.

Unless you identify your internal yardstick for completion, you will always feel incomplete. You will always move the goal posts. You will always want more. Contentment will always lie just beyond your grasp. 

One question to ponder in your thinking time: What is my personal definition of enough? 

Make an Impact!
Jay Papasan
Co-author of The ONE Thing, The Millionaire Real Estate Agent & author of The Rookie Real Estate Agent