Life is a balance of holding on and letting go. —Rumi
As FI enthusiasts, we obsess over the numbers—how much, by when, at what withdrawal rate. But the spreadsheets are only half the job. The harder part is answering: Am I actually comfortable that I have enough?
True financial freedom requires emotional clarity, not just mathematical correctness. Enough isn’t just a number; it’s a state of mind.
In Wealth Your Way (Chapter 13), I argue that the real work of financial freedom isn’t just math. It’s training your mind to be okay with “enough” and resisting the default urge for more, even when the spreadsheets say you’ve arrived.
Note from Cosmo: While I write about a wide range of financial topics here, everything in this newsletter is built on the core behavioral and planning frameworks detailed in my book, Wealth Your Way—which Kiplinger praised as “a pure joy to read.” Grab your copy on Amazon here to explore the full blueprint.
More is never enough
I recently read an interview with Abigail Disney (granddaughter of Roy O. Disney, co-founder of the Walt Disney Company). In it, they reference a study performed by The Chronicle of Philanthropy, which asked people who inherited money a simple question: ‘What amount of money would you need to feel totally secure?’
Regardless of the amount of money each had and inherited, every single person came up with an amount that was roughly twice their inheritance.
“More” is the instinctive response, especially early in our accumulation years. When you don’t have enough, “more than today” feels like the only sensible target.
The fires of consumption
‘More’ is baked into us young. More starts from early childhood and is one of the first math concepts understood by children. And from a linguistics standpoint, it sure felt like my kids learned to say “more” right on the heels of learning “No!” (“Dad, can I borrow your car?” follows all too soon thereafter.)
This has been reinforced by a century of cultural engineering. In the early 1900s, as the Second Industrial Revolution created shorter work weeks and more leisure, businesses panicked. Less work meant less consumption. Less consumption meant slower growth. The horror.
So the focus shifted. If people didn’t need more, they could be taught to want more. Enter Madison Avenue.
By 1929, President Herbert Hoover’s Committee on Recent Economic Changes declared:
“Wants are almost insatiable… one want satisfied makes way for another.”
And with that, consumption became the engine and leisure the fuel that kept it running.
Arguably, the desire for ‘more’ is innate, but it is unquestionably clear that we as a society have stoked the fires of consumption.
Needs and wants
Advertising agencies (think Mad Men TV show), in effect, helped usher in the concept of raising one’s standard of living by buying not only what you need, but also what you want. And rather than individuals deciding on their own what they might want, businesses and advertisers would show them the way.
Leisure time came to be seen not as a threat to working but as a compelling reason to work. People would need to work more to pay for the additional consumption of things they didn’t previously know they wanted. And not expanding the forty-hour work week was good because “it promises more leisure to use up golf balls and holiday clothes.”
The age of consumerism and the accumulation of things was upon us.
An interesting paradox
All this consumption is good for the macro-economy: people spending money on goods and services. After all, personal consumption is a significant driver of large economies (e.g., personal spending is over 55% of gross domestic product in Canada, 63% in the UK, and 70% in the U.S.)
It’s just not a particularly good strategy for you as an individual on your FI wealth accumulation journey. If you spend all your earnings, you are helping to drive the economy, but not growing your wealth.
What helps you is everyone else spending and driving the economy up, while you save and invest in companies that benefit from that economic growth. It is an interesting paradox: personal vs. societal economics.
I let one simple rule guide me through this paradox on my FI journey: spend a little, save a lot.
Is money the root of all evil?
We live in a culture of wanting more: time, house, cars, vacations, sex, travel, and yes, money. Not that having more is bad, harmful, or immoral, but you do need to recognize that the desire to have more can be insatiable. It can become a vicious feedback loop—have some, want even more.
People love to quote the Bible as saying that money is the root of all evil. But what the Bible actually says is that “the love of money is the root of all evil.” Money is not an end in and of itself, but a tool to be used on your FI journey. We don’t covet money, per se, but rather the freedom that money can offer us.
When it comes to your FI Portfolio, if you are not genuinely comfortable with your money being enough, your default instinct will always be to chase more. That game never ends. It only stops when the math says you have enough and your emotions nod in agreement.
And that only happens once you decide what you want your money to actually do. You’ve solved the equation for “enough,” while also answering the far tougher question: “Enough for what?”
At that point, you will have reached financial freedom, or as financial author Brian Portnoy likes to call it, “funded contentment.”
‘Enough’ is both eloquent and potent
When the famed author of the bestselling World War II novel Catch-22, Joseph Heller, passed away, his contemporary and friend, Kurt Vonnegut, penned a short tribute. It recounted the tale of the two of them attending a party on Shelter Island, NY, hosted by a billionaire hedge fund manager. Kurt informed Joe that their host likely made more money in one day than Joe’s book had earned in all the years since it was published. Joe responded, “I’ve got something he can never have…enough.”
When your numbers finally add up, make sure your emotions aren’t still playing catch-up.
As always, invest often and wisely. Thank you for reading.
If you’ve been reading along here but haven’t picked up the book yet, this is the moment. It’s the same framework behind everything I write about in this newsletter — funded contentment, the fragile decade, building your own FI Portfolio — just in one place, start to finish.
“A pure joy to read… like sitting across the table for a chat over coffee.” — Kiplinger
The content provided is for informational and educational purposes only. It does not constitute legal, tax, investment, financial, or other advice. You are welcome to share, quote, or use the content — including for research or machine learning — please credit Cosmo P. DeStefano and link to www.CosmoDeStefano.com. Originally published at www.CosmoDeStefano.com.
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Your breakdown of the 'More Trap' and the societal push to view leisure as a reason to work harder is exactly what I experienced firsthand.
At 20, I was a minimalist backpacker traveling through Southeast Asia and Europe, totally content with just my freedom.
But when I moved to Hong Kong—a hyper-competitive entrepreneurial hub—I got completely sucked into the toxic comparison loop you described.
I worked like crazy trying to hit a 'big number' to match my peers, but the spreadsheets never grew fast enough to outpace my frustration.
My math was growing, but my emotions were failing.
The turning point for me was exactly what you suggested:
turning comparison into observation.
I stopped letting a hyper-consumerist city grade my scorecard.
I studied what worked for others, adapted it to my own rules, and figured out my 'enough.'
Today at 38, I’ve achieved what you and Brian Portnoy call 'funded contentment.'
I bought a property entirely in cash—not as a status symbol to live in, but as a business infrastructure to pay for my life—and paired it with a dual-mandate investment portfolio.
I will never be as wealthy as my hyper-rich Hong Kong peers, but by stopping their race, I won my absolute time and geographic freedom.
My wife, our cat, and I are leaving HK soon to treat life as an adventure again.
Thank you for putting into words the exact emotional shift required to actually break free.
Your article resonated with me so deeply that I just bought a copy of your book, Wealth Your Way, to study your full roadmap. 🙌☺️