I was standing at the counter of a McDonald’s near our house, doing math in my head.
This was the last year I taught school. The whole family was there to get a Saturday afternoon lunch while we were out running errands. The kids were little, and my son was working his way down the menu board. He always had a knack for ordering the most expensive thing on the restaurant and even adding bacon if he could. So there he was, like normal, hunting for the most expensive thing on it. He found it. Then he asked if he could add bacon. Typical!
I told him no. “You’re getting a kid’s meal. Period.”
Then I turned to Kristie and said something I still remember word for word. I cannot wait until the day comes when I can walk into a restaurant and not care what it costs.
The Day Showed Up Without Announcing Itself
That day came. The following spring, my teaching contract got canceled. Faced with the sheer desperation of needing to find a way to pay the bills, I ended up starting a company, and then over the course of the next few years, somewhere in there, the math stopped mattering at restaurants.
I can’t tell you when. There wasn’t a specific visit to a restaurant where I looked at the receipt and commented about the price and how I didn’t care.
It happened without me seeing it, and honestly, that’s the way most change happens. Change usually happens slowly and without any ceremony attached to it. There was a point in time where I was aware of the fact that I hadn’t really looked at prices on a menu in a while.
That was the last time money changed my life. I’ve made a lot more of it since, and none of that changed anything.
Now Answer the Question Yourself
When did more money last change your life?
Take a second with it. Not the last raise. The last time a bigger number actually altered how your days felt.
Most people can answer that question. But what probably surprises you about that answer is how long ago it happened. For a lot of successful people it’s ten years ago, fifteen, sometimes further. Which means they’ve been climbing for a decade up a hill that gets steeper and steeper.
My Last Teaching Salary Was $38,000
So what’s the point to all of this? Let me tell you a little bit more about my personal story before we go there.
The last year I taught school, my salary was around $38,000. The first check I got from a customer after I started my company was $18,000. Nearly half a year’s teaching salary, in one payment. I remember what that felt like in my chest.
The second check was $686,000.
That one took a while to get used to. But at some point, I did. And really, that’s what we’re talking about in this article. Every number I’ve hit since then has been bigger, and not one of them has done what the $18,000 did.
You see, over time it takes a lot more money to move the needle.
The Research Fight That Finally Got Settled
This isn’t just my experience. There’s a well-documented argument about money and happiness that ran for over a decade in the research world. I think it’s really interesting and highlights something that most people never think about because it reveals one of the lies that we believe about money.
In 2010, Daniel Kahneman and Angus Deaton published a study finding that emotional wellbeing rose with income up to about $75,000 a year and then flattened out. That number got repeated everywhere. You’ve probably heard it quoted at a dinner table. It’s been in practically every TED talk and conference talk since that study came out, and the whole purpose of people using that is to prove that money doesn’t buy happiness. But it’s based on incomplete data.
Then in 2021, Matthew Killingsworth at Wharton ran the question again using a different method, pinging people on their phones in real time instead of asking them to recall a whole day. He found no plateau at all. The study found that happiness kept rising with income well past $75,000, with no ceiling in sight.
So what we have here are two respected researchers contradicting each other on the same topic, which you might think would lead to them arguing and calling each other frauds in journals and in articles all over the internet.
What They Found When They Stopped Arguing
Instead of trading rebuttals for another ten years, they did something I wish more people did. They pooled their raw data, reanalyzed it together with a neutral third party, and published a joint paper in 2023 called “Income and emotional well-being: A conflict resolved.”
The answer to how money affects you, boiled down to who you already are before money enters the equation. For most people, happiness does keep rising with income, well past $100,000, and for the happiest group it even accelerates. There’s an unhappy minority whose happiness rises only to about $100,000 and then goes flat. Did you see that? Money keeps buying happiness for people who are already happy.
I wrote about that side of it a few weeks ago in Money CAN Buy Happiness, and I stand by every word. Money buys real things. It fixes real problems.
But it can only fix what money can fix.
But there’s a second half to that research that is typically ignored, and it explains the McDonald’s story I shared earlier.
Every Step Costs Double the One Before It
The relationship between money and happiness isn’t a straight line. It runs against the logarithm of income, which is a technical way of saying something very simple: “To feel the same gain twice, you have to double your money. Not add to it. Double it.”
Watch how that plays out:
- $50,000 to $100,000. That’s a doubling. When someone goes from making $50,000 a year to $100,000 a year, life changes, and you can feel it.
- $100,000 to $150,000. $50k more, same as the last jump. Nothing much changes.
- $400,000 to $600,000. Another $200k is not nothing, but believe it or not, at that income level, things don’t meaningfully change.
- $400,000 to $800,000. Now you’re back in business. Because it’s a double. Life is materially different, making $800,000 a year versus $400,000 a year. And if you are there, you know what I mean.
So the price of the next real change keeps going up while the size of the change stays the same. You’re chasing a moving target up a hill that gets steeper every year. And honestly, it never stops working because if it did, we would stop climbing the hill. We’re just not being honest with ourselves about how far we must climb between each meaningful change in our life with higher income.
What Makes It the Perfect Trap
There’s no wall to hit. There’s not a dollar amount where this stops working.
If it did, you stop. If something broke along the way, you would stop. Nothing here breaks. The revenue keeps climbing, the accounts keep growing, the numbers keep going the right direction, and the whole time you’re getting less and less back per dollar without a single warning light coming on.
Ten years ago, enough for me was a modest house on half an acre. Today the number in my head is a much bigger house on more than a half acre. The definition moved and I didn’t authorize the move…it just happened.
The Part That Took Me Longest to Realize
Here’s what I finally worked out, and I didn’t have it until recently.
The thing most successful people want now isn’t a bigger number. Ask them what they’d do if they hit their number and they’ll tell you they’d relax. Breathe. Take three months. Stop feeling like something’s chasing them.
But think about it: You can’t buy that.
Not because money is powerless. Money fixes what it can fix, and it won’t fix what it can’t fix. It’ll buy you a spa weekend and a very nice vacation. What it can’t do is give you breathing room, because the reason you don’t have breathing room is the chase itself.
You created the problem with money. Now you’re trying to use money to solve it. That’s a loop, and you can run it for 20 years without noticing you’re in it. This is the same trap I described in More Money Doesn’t Buy Freedom.
Two Questions for This Week
Don’t turn this into a project. But what I would encourage you to do is answer two questions. It’s only going to take about 10 minutes and a single piece of paper.
First question. What number would finally let you do the thing you actually want to do? Write the number down. Most people have it within a few seconds, which tells you they’ve been carrying it around a while.
Second question. What’s the smallest honest version of that thing you could do inside the next 12 months without hitting the number?
For most people, there’s a real gap between those two answers, and the gap is embarrassing. You could do a version of it this year. But you haven’t because you’ve been waiting on a number to give you permission, and permission was never what the number was for.
If you don’t like where that lands, Later Never Comes covers what happens to people who keep postponing the thing.
Words of Wisdom
“Do not wear yourself out to get rich; do not trust your own cleverness. Cast but a glance at riches, and they are gone, for they will surely sprout wings and fly off like an eagle to the sky.” – Proverb 23:4-5
That one has convicted me and my ambitions more than once. It doesn’t say money is bad, and it doesn’t tell you to stay poor. It warns about wearing yourself out for something that grows wings.
Which is a pretty good description of a curve that flattens while you keep climbing.
Before You Go…
What’s Real? goes out every Wednesday. One lie dismantled, one truth delivered, with the research behind it. If you’d rather have it land in your inbox than check back here, subscribe at therealjasonduncan.com.
And if you run a company or belong to an association that puts on events, and you’d want this kind of talk on the stage, I’m booking keynotes for 2027. Details are at therealjasonduncan.com/speaking.
– The Real Jason Duncan