When Crushing it Leaves us Feeling Crushed

Over my 20 years in wealth management, I’ve met some incredibly successful people. Folks with strong incomes, impressive net worths, and careers that most people would likely envy. And they’re exhausted.

But not in the way you’d expect. It’s not necessarily from too many meetings, too much traveling, or too much pressure. It’s because every time they achieve a milestone, the finish line simply moves further out.

Burnout is everywhere right now.

SHRM research found that 44% of U.S. employees feel burned out at work, 45% feel emotionally drained, and 51% feel "used up" at the end of the workday. Gallup's State of the Global Workplace report shows employee engagement declining for the second consecutive year, costing the world economy an estimated $10 trillion.

Most of the research points to workplace conditions, which is fair. But some of the most burned-out people I've met were in high-paying roles with lots of autonomy. So what was burning them out?

Among high achievers, there’s another factor that rarely gets talked about: the never-ending pursuit of more. More money. More status. More recognition. More achievement.

They never defined what “enough” means for them, based on their intrinsic values. And when your goals are based on societal or employer expectations, success becomes a moving target. So you never stop chasing and, eventually, exhaustion sets in.

Does more money make you happier?

If you expected me to say no, and perhaps give you the canned “money doesn’t buy happiness” explanation, the answer may come as a surprise. Because money actually does make you happier. But there’s important nuance to this.

A while back, I went looking to see whether anyone had studied the gap between having enough and feeling like you have enough. I found two researchers who'd spent more than a decade publicly debating that exact question.

Writing in the Proceedings of the National Academy of Sciences in 2010, Daniel Kahneman and Angus Deaton reported that day-to-day happiness climbed alongside household income and then flattened out around $75,000.

Eleven years later, in the same journal, Matthew Killingsworth put the question to tens of thousands of people through real-time smartphone surveys and found no flattening at all.

Disagreements like that don't usually get resolved. Both sides publish their findings, the field picks a favorite, and the question goes cold.

But in 2023, Kahneman and Killingsworth did something academics almost never do. They ran what's called an adversarial collaboration, sitting down to work on the problem together, with a third researcher, Barbara Mellers, refereeing between them.

What they found was one of the most useful things I'd read about money in a long time.

On average, more income really does keep making people happier, well past $75,000, with no ceiling in sight. But the least happy 20% turned out to be a different story. For that group, happiness rose with household income until roughly $100,000. And then it stopped.

The money kept coming in for them. It just stopped delivering any reward, which is an unsettling thing to discover when you've organized your life around earning it.

If you aren't in that 20%, I expect the rest of it sounds like good news. It took me a while to see why it isn't.

A line with no ceiling is a line that never tells you to stop. Earn more, feel a little better, and on it goes. There's no point on that graph where the numbers announce you've arrived.

That’s not something money was ever able to do. It can buy the house, the school tuition, the runway to walk away from a job you've outgrown. What it can't do is tell you when you have enough of it.

That's what I listen for now when someone tells me they need more. Usually, it isn't that they lack enough. It's that they've never defined what enough would be, so the target keeps moving. And how would you know you'd arrived somewhere you never described?

Is this only a high earner’s problem?

It isn't, and that's the part I find people least expect. I've watched the same restlessness in someone with $300,000 saved and in someone with $3 million, and from the inside it looks about the same.

What changes from one to the other isn't the feeling. It's the size of the number they've pinned that feeling to, and the number they name is almost never the one they'd need.

Someone will tell me, with real conviction, that they need a certain amount saved before they can breathe comfortably. Let's say it's $4 million. So, we sit down and run the numbers together: their income, expenses, and what a portfolio can reasonably be expected to produce over their remaining earning years.

And the figure that would let them rest easier often turns out to be significantly lower, maybe something closer to $2.5 million.

It isn't that I'm running optimistic projections. It's that nobody had ever asked them what enough would require, so the biggest number they could reasonably picture became the number they set as their goal.

How do you decide what enough means?

Nobody ever asked me either. It took two battles with cancer to make me sit down and answer the question for myself.

When you're made to count the years you might have left, you start asking what you'd been planning to spend them on. That's when I stopped focusing on the goalposts and started asking what I actually wanted to be running toward.

The answer, once I let myself say it out loud, was more modest than I'd expected. Enough turned out to be work I enjoyed and could do from anywhere, a decent income to supplement my wife’s, and the flexibility to spend afternoons with my kids.

None of which means you should want less. Enough isn't the opposite of ambition. It's what keeps ambition from consuming you.

The most driven people I’ve worked with, and I mean the ones who still seem to enjoy their lives, aren't the ones reaching for the most. They're the ones who sat down and named what they were after, and why, and what would tell them they'd gotten there.

So, let me leave you with the question I had to answer for myself. Have you decided what enough looks like for you?

If a number just came to mind, pay attention to where you got it from, because most of us are carrying around someone else’s. Maybe it came from your industry, or the home you grew up in, or whoever you were measuring yourself against at twenty-five.

There's nothing wrong with those numbers on the face of it. They're just not yours. A number only becomes yours when you know what it's for. Decide that, and you'll feel it when you get there.