Episode 390

When Was the Last Time More Money Actually Changed Your Life?

September 2, 2026 · 10 min
Jason Duncan

About this Episode

Most people can name the last time more money genuinely changed their life. What almost nobody can explain is why it stopped, or why they kept chasing the next number anyway.

Jason opens with a scene from his last year teaching school, doing budget math at a McDonald's counter while his son hunted for the most expensive thing on the menu. Then he traces what happened after the money showed up: a thirty-eight thousand dollar teaching salary, an eighteen thousand dollar first check that he still remembers in his chest, and a six hundred eighty-six thousand dollar second check that eventually stopped feeling like anything at all.

He walks through the research that finally settled the income-and-happiness argument, including why every equal gain in how your life feels now requires doubling your income rather than adding to it. Then he gets to the part that costs the most: the breathing room you're chasing can't be purchased, because the chase itself is what took it from you.

Two questions, ten minutes, one piece of paper. Most people find the gap between their answers embarrassing.

Read the full post: https://therealjasonduncan.com/articles/390

Book a call with Jason: https://therealjasonduncan.com/talk

New episodes every Wednesday.

Full blog post: https://therealjasonduncan.com/articles/390

Episode page: https://therealjasonduncan.com/podcast/390

Book a call with Jason: https://therealjasonduncan.com/talk

Sponsor – Bank on Yourself: https://therealjasonduncan.com/bankonyourself

Kahneman & Deaton (2010), "High income improves evaluation of life but not emotional well-being," PNAS Killingsworth (2021), "Experienced well-being rises with income, even above $75,000 per year," PNAS Killingsworth, Kahneman & Mellers (2023), "Income and emotional well-being: A conflict resolved," PNAS: https://www.pnas.org/doi/10.1073/pnas.2208661120

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There was a day you couldn't afford the thing you wanted.

And then there was a day you could, and you didn't even notice it happen.

## INTRO BLOCK

Welcome to The Real Jason Duncan Podcast.

This whole show runs on one idea: to expose the lies you believe and the truths you don't. Most of us have believed things for a long time that just weren't true, and when you finally see the truth, it changes things.

The most dangerous lies don't look like lies. They look like success. They look like golden cages, where the bars are covered in gold so you can't see them, and as a result people like you and me get deceived, because the lies that trap us look like good things, they look like truth, they look like wisdom.

Maybe there's something you used to believe that kept you trapped and you are so glad you don't believe it anymore. Maybe there's something you still believe, and you don't realize that it's keeping you trapped. This show is about helping you break free from that cage.

I expose these lies twice a week.

Every Monday, I interview someone who believed one of those lies. We talk about what they used to believe, why they don't believe it anymore, and what it costs people to stay stuck inside that lie for another five years.

On Wednesdays, just like today, I bring you a special edition, where I read you a version of the article I write for my newsletter every Wednesday called What's Real?

You can subscribe free at therealjasonduncan.com/articles, and it hits your inbox every Wednesday morning before this episode drops.

This week's post is called "When Was the Last Time More Money Actually Changed Your Life?"

## BODY

Years ago I was standing at the counter of a McDonald's near our house, doing math in my head.

This was the last year I was a middle school history teacher. The whole family had stopped in for lunch on a Saturday while we were out running errands, and my son was working his way down that menu board hunting for the most expensive thing on it. He found it. Then he asked if he could add bacon.

I told him no. He was getting a kid's meal, period.

And 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.

That day eventually came. The following spring my teaching contract got canceled, and out of pure desperation to pay the bills, I started a company. Somewhere over the next few years, the math just stopped mattering at restaurants.

I can't tell you when exactly. There was no dinner where I looked at the check and had some big realization. It happened the way most change happens, which is slowly, with no ceremony attached to it at all. At some point I just noticed I hadn't looked at prices on a menu in a while.

And that was the last time money changed my life.

Now the weird part is that I've made a whole lot more of it since then, and none of that ever did what that first stretch did.

So let me ask you the same question I've been asking myself. When did more money last change your life?

Not the last raise. Not the last good year. The last time a bigger number actually altered how your days felt.

Most people can answer that. And what surprises them is how far back the answer sits.

Here's my own math on it. My last teaching salary was around thirty-eight thousand dollars a year. The first check I got from a customer after I started my company was eighteen thousand dollars, which was nearly half a year's salary in one payment, and I remember exactly what that felt like in my chest.

The second check was six hundred eighty-six thousand dollars.

That one took a while to get used to. But at some point, I did. And every number I've hit since has been bigger without ever doing what that eighteen thousand did.

There's real research behind this, by the way. Back in twenty ten, Daniel Kahneman and Angus Deaton found that emotional wellbeing rose with income up to about seventy-five thousand dollars a year, and then it flattened out. You've probably heard that number quoted in just about every conference talk since.

Then eleven years later, Matthew Killingsworth at Wharton ran the whole thing again a different way, and he found no plateau at all.

Two respected researchers, flatly contradicting each other. And instead of fighting about it for another decade, the two of them pooled their raw data, brought in a neutral third party, and published a joint paper in twenty twenty-three that showed why they were both right.

Money does keep buying happiness for most people, well past seventy-five thousand, past a hundred thousand, and beyond.

But it runs against the logarithm of income, which is a technical way of saying something very simple. Each time you want to feel that change again, it costs twice what it did the last time.

Go from fifty thousand to a hundred thousand, and your life changes. You feel it. Go from a hundred thousand to a hundred fifty, and it's that exact same fifty thousand dollar raise, and almost nothing changes. But go from four hundred thousand a year to eight hundred thousand, and things move again. Because that's a double.

So you're chasing a moving target up a hill that gets steeper every single year, and there's no wall to hit. No warning light comes on.

Ten years ago, enough for me was a modest house on half an acre and a couple of decent cars. Let's just say my enough changed as zeros got added to the number in my head. The definition moved, and I never authorized the move.

Now here's the piece I only figured out recently.

What most successful people want at this point isn't a bigger number. Ask them what they'd do if they hit it and they'll tell you they'd relax. Take three months. Stop feeling like something is chasing them.

You can't buy that.

Money fixes what it can fix, and it won't fix what it can't fix. It'll buy you a spa weekend. What it can't buy you is breathing room, because the chase itself is the reason you don't have any.

You created the problem with money. And now you're trying to use money to solve it. That's a loop, and you can run it for twenty years without ever noticing you're in it.

## SPONSOR BRIDGE AND READ

Which brings me to something I want to tell you about, because it's connected.

Most people never think about the fact that every dollar they finance through a bank is a dollar of interest they hand to somebody else and never see again. You earn it, you spend it, and the growth on it belongs to the lender. That's a cage most people never look at directly, because it's just how everybody does it.

Bank on Yourself is built around a different idea. You use a specially designed dividend-paying whole life policy as your own financing system. Your cash value keeps growing whether you've borrowed against it or not, and when you buy the truck or fund the deal, you're paying yourself back instead of a bank.

I'm not going to explain the whole thing in ninety seconds. Go look at it yourself at therealjasonduncan.com/bankonyourself. That's therealjasonduncan.com/bankonyourself.

## WHAT TO DO ABOUT IT

So what do you actually do with all this?

Take ten minutes this week and one piece of paper, and answer two questions.

First one. What number would finally let you do the thing you actually want to do? Write it down, and notice how fast it came to you.

Second one. What's the smallest honest version of that thing you could do inside the next twelve months without hitting that number?

For most people there's a real gap between those two answers, and the gap is embarrassing. Maybe the answer to the first question is more time with your grandkids, or more travel. You could do a version of that this year. And you haven't, because you've been waiting on a number to give you permission.

Permission was never what the number was for.

Now for a lot of you listening, the reason you can't do the thing isn't the number at all. It's that the business doesn't run without you. There's no version of three months off that doesn't cost you something.

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 twenty twenty-seven. Go to therealjasonduncan.com/speaking. That's therealjasonduncan.com, slash, S-P-E-A-K-I-N-G. The link is in the show notes.

## WORDS OF WISDOM

There's a proverb that lands right on this. Proverbs twenty-three, verses four and five.

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.

I try to read from Proverbs almost every single day, and those two verses have convicted me and my ambitions more than once. It doesn't say money is bad. It doesn't tell you to stay poor. It warns you about wearing yourself out for something that grows wings.

Which is a pretty good description of a curve that flattens out while you keep climbing.

Go read the full post at therealjasonduncan.com/articles. And if you can name the last time money changed your life and it was more than five years ago, I'd like to hear what it was. Hit reply on the newsletter. I read every one of them.

As always, I am your host, The Real Jason Duncan, and Jesus is King.