How Happy Do You Need to Be to Be Happy with Money?

The key ingredients of well-being, with a dash of '90s nostalgia

Hi all,

I want to give a quick shoutout to those who have recently shared my posts. There isn’t always a way to reach out directly and say thank you, so if you’ve shared one of my articles and are reading this, well, thank you!

In other news, I seem to be settling into a bi-weekly cadence. With another project I’ve launched, this rhythm works for now. Hopefully, it also gives you a little more time to sit with each post. If you want more, then feel free to comment or shoot me a message and demand it.

In this edition:

• The stories we tell about money and happiness, and why many of them are more myth than fact

• The science and art behind why happiness often comes before money in the relationship between the two

• Okay, enough about money and happiness, let’s reminince a little about the ’90s

Before primetime TV, billions of dollars and a contact list filled with celebrities, there was powdered milk.

Under the Texas sun, the man went door to door, pitching powdered milk as a cost and time saver. The people who simply closed their doors couldn’t possibly know how differently they would one day think of the face they had just shut out. It wouldn’t be the powdered milk salesman they remembered. It would be Mark Cuban: tech billionaire, NBA team owner, Shark Tank investor.

It’s reasonable to think the happiness of the door-to-door salesman Mark Cuban versus the Dallas Mavericks owner Mark Cuban must be vastly different. Of course it has to be. But maybe not to the extent we assume.

As he once said in an interview:

“Money buys you comfort. Money buys you sanity in some respects. Money takes away a lot of the stress of paying the bills, but it doesn’t make you happy. I was happy when I was broke.

If you were miserable when you were broke, money is not gonna change that.”

Take a medieval king and drop him into the home of the average family today and he just might bow. By many measures, we may be wealthier than ever. Yet survey after survey points to an alarming level of unhappiness.

People are spending more time alone, growing more worried about the future of work and their sense of purpose, and increasingly drifting toward nihilism.

While objectively we may be as rich as ever, we also seem to be as miserable as ever.

To me, this reflects one of modern life’s enduring mysteries: the relationship between money and happiness.

Years ago, economist Richard Easterlin found that happiness in the United States remained largely stagnant despite large increases in average real personal income. In what’s now known as the Easterlin paradox, wealthier individuals report greater happiness at any given moment, but average happiness does not rise as societies get richer.

In a way, the chart looks to be saying, “You don’t need a lot of money to be happy, and a lot more money won’t make you any happier.”

It reinforces our familiar cautionary tales about wealth, portrayed in fiction by figures like Jay Gatsby or Scrooge — men with great wealth but lonely, cold hearts. History offers its own examples, too, like Cornelius Vanderbilt, whose lasting legacy is less about happiness or affection and more about being a ruthless businessman, one who created many enemies and made life difficult for his family.

And yet there are many examples that don’t fit the narrative. Take MacKenzie Scott, as a recent one, who has committed herself to using her Amazon fortune for altruistic purposes, donating an estimated $26 billion.

It’s said that money changes people. But maybe money mostly magnifies parts of us, including parts we didn’t even know were already there.

Money can make you happier — but not without happiness first

There’s a persistent fascination with lottery winners who go broke. The scenario might be playing itself out in your head right now: a person buys the winning ticket, then buys too big a house, buys too many cars, gives too much away to friends and long-lost relatives, forgets to pay taxes, until the fairy tale lifestyle is finally repossessed.

Because money can’t buy happiness, right?

Well, it turns out there’s evidence that most lottery winners actually do live happily ever after. One study of lotto winners found that winning the lottery improved the winners’ sense of overall life satisfaction. And the more they won, the greater the impact.

Similarly, our long-held belief that money can’t buy happiness appeared to be validated by research suggesting happiness plateaued around $75,000 a year.

But further research found something more nuanced. On average, happiness continued to rise with income well beyond $75,000, with no clear plateau.

However, there was an important caveat.

For a subset of people who were already unhappy, happiness rose with income up to about $100,000 — and then leveled off. For others, happiness continued to rise. And for the happiest group, it even accelerated.

One of the study’s authors summed it up this way:

“If you’re rich and miserable, more money won’t help. For everyone else, more money was associated with higher happiness, to varying degrees.”

In other words, if you become rich, you’re still the same you but just richer. Wealth can offer many blessings, but it can’t exorcise any demons.

I imagine it like arriving at a tropical getaway only to discover you can’t take off your winter coat — sealed tight by past experiences, trauma or misplaced expectations.

So, the research suggests more money can mean more happiness. But more importantly, it confirms that money is far from the biggest contributor to one’s happiness. It can’t solve all the problems that make us unhappy, nor nurture all the things that make us happy.

As Cuban’s story suggests, a man can be happy selling door to door, just as he can be happy cheering his own professional team from the courtside floor.

All this time we’ve been asking, How much money do I need to be happy? when the more pertinent question may be, How much happiness do I need to enjoy more money?

How much happiness do you need? Enough to make happy little trees

One of the joys of growing up before streaming was being forced to explore TV channels. And if you lived in 1990s America, chances are you landed on PBS at least once and found a man with a bushy hazel afro, scruffy beard and collared shirt with the top buttons undone.

This was Bob Ross, famous for painting serene landscapes dotted with “happy trees.” Through his soothing instruction, he often reminded viewers:

“There are no mistakes, only happy accidents.”

Whole lotta happiness in one photo

Whether he meant to or not, Ross touched on something true about happiness: it’s more art than science. More Rorschach than blueprint. In the eye of the beholder. One person finds happiness at an all-inclusive tropical resort. Another seeks it in a solitary monastery atop a mountain. An errant stroke of the brush can be the trunk of a strong, towering pine.

It’s why there’s so little consensus on how to measure happiness at all.

Experts generally distinguish between two dimensions: hedonic well-being, the day-to-day experience of pleasure, and evaluative well-being, how people think about their lives as a whole, including purpose and meaning.

A cold beer might make me happier tonight. But raising my kids to be successful and kind people — maybe marked by a couple cold ones with them, too — is what makes me feel I’ve lived a happy life.

What ultimately makes us happy is something we’ve wrestled with for centuries. Aristotle, in the fourth century B.C., described “eudaimonia” as the highest aim of human life — not fleeting pleasure, but living well through virtue.

Over time, the focus kept inching inward. Today, happiness is measured by optimized desires and possessions — the manicured lawn, the new phone, the staged social photo — until happiness becomes what we have and how we look.

Maybe the solution isn’t reaching some required level of happiness, but learning to look for it in the right places.

Modern happiness research suggests that well-being is built from a familiar set of ingredients: relationships; meaning or purpose; awe through nature or faith; health; gratitude; service to others.

These aren’t things you accumulate; you nurture them. They can be done for free, though money can greatly support them by enabling experiences, generosity and time.

The way I see it, just as money alone won’t make you happy, the pursuit of happiness won’t either. It’s the act of doing — connecting, creating, learning, growing, serving, appreciating, belonging — that produces life satisfaction.

So it isn’t a question of how much happiness you have, but whether you have immovable things in place to attach to, things that keep you grounded through happiness’s inevitable rises and falls.

As the lead character in Anton Chekhov’s short story Gooseberries observes:

“Behind the door of every contented, happy man there ought to be someone standing with a little hammer and continually reminding him with a knock that there are unhappy people, that however happy he may be, life will sooner of later show him its claws, and trouble will come to him — illness, poverty, losses, and then no one will see or hear him, just as now he nieghter see nor hears others.”

The pursuit of money or happiness alone is hollow, filled with empty expectations that can’t support the weight of a fully lived life. It’s the proverbial rocks — family, friends, purpose —that we can’t forget about to help keep us moored through the highs and lows.

That’s why I think the relationship between money and happiness is so messy. Even together they just aren’t big enough to show the whole picture of life.

Like Bob Ross reminds us, happiness is in the creating, not the finished painting.

Because it’s not the accumulation that matters in the end. No one reads obituaries for bank balances.

Refuge from the melancholy and infinite sadness

Some research suggests that simply thinking about money can make us more self-centered. And that self-absorption can slip into a kind of persistent unhappiness — an infinite sadness, if you will.

Infinite Sadness happens to be part of the title of a classic album by the ’90s band, The Smashing Pumpkins, whose lead singer, Billy Corgan, has articulated what I think is one of the clearest reflections on the uneasy dance between money, success and happiness.

Shout out to those who had the double disc!

Having achieved great fame and wealth by his mid-20s, Corgan struggled with the realization that “all of it is transactional.”

He said: “No matter how many hit songs you write, it’s always about the next one. No matter how many records you sell, there’s always somebody who’s going to sell more records than you.”

Later, after growing older and starting a family, he came to understand:

“Only unconditional love in some facet of your life gives you the proper perspective to appreciate what is great about transactional things — and to see them for what they are, which is transactional.

When I stand in front of 65,000 people, in my hierarchical mind my family is still above that.

Only unconditional love clarifies what’s great and what’s not great about it.”

Only when you have sources of unconditional love in your life can you be happy enough to see money clearly, to use it for joyful things without letting it become the most important thing.

Rich or poor, you can hope. You can feel gratitude. You can be kind. None of this insulates you from hardship, but it helps you move forward — to appreciate things when happiness ticks up and to not give up when it falls.

I don’t think there will ever be a definitive answer to the relationship between money and happiness. And that, in itself, may be the answer.

As the lyrics of one of Corgan’s songs go:

“Happiness will make you wonder

Will I feel okay?

It scares the disenchanted far away.”

Notes to my future self:

• Wealth can offer many blessings, but it can’t exorcise any demons.

• The pursuit of money or happiness alone is hollow, filled with empty expectations that can’t support the weight of a fully lived life.

• Only when you have sources of unconditional love in your life can you be happy enough to see money clearly, to use it for joyful things without letting it become the most important thing.

With gratitude,

J.S.