The Man Who Couldn’t Chill (Part II)

Last week’s letter hit a nerve. 
A psychologist reached out asking if The Man Who Couldn’t Chill was real. 

Yes. Very real. (and then he asked if he could work with him!)  

This week, I spoke with The Man Who Couldn’t Chill again. 

He said something that stopped me: 

“Couldn’t I just sell everything? Move it into safe investments earning 5 to 7 percent, cover my expenses, and be done? Why am I still hustling?” 

He’s not in crisis. 
He’s burdened by his success. 

The very things that once energized him—the chase, the deals, the control—now feel heavy. What once felt like mastery now feels like maintenance. And when you reach that point, it’s disorienting. You’ve climbed so high that there’s nowhere left to go except across to the next mountain. 

I told him to read From Strength to Strength by Arthur Brooks and The Second Mountain by David Brooks. He promised he would. But even before opening a page, he said something that revealed what most quietly burdened millionaires feel: 

“I thought I was the only one.” 

That’s the part that gets me every time. 
Because I’ve been writing and talking about the Quiet Burden since the early days of Members’ Wealth, but when someone feels it for the first time, it’s like they’re hearing it in a new language. Awareness doesn’t always arrive when spoken. It lands when you’re ready to hear it. 

My younger brother once said something that reframed it perfectly. 
He told me, “Wisdom isn’t wasted on the young. It just lies dormant until something triggers it.” 

That line stuck. 
It’s true of wisdom, and it’s true of marketing, leadership, even healing. People rarely change after one conversation. It takes a mosaic of moments, a series of small awakenings, before the message finally clicks. 

And that’s exactly how it works with the quietly burdened. 
First, they must feel the burden. 
Then, they must know they’re not alone. 

Only then can the work begin. 

Because here’s the truth: 
You’re functional, but not free. 
You’ve optimized yourself into a success prison. 
You’re carrying an identity that once served you but now owns you. 

That’s why I keep returning to the Buddhist parable of the raft, and how I’ve come to extend it. 

You build a raft to cross the river. 
It gets you where you needed to go. 
But then you try carrying it up a mountain. Ridiculous, right? 
So you burn eighty percent of it for warmth, use the remaining twenty percent to build a backpack, and keep climbing. 

Then, as you ascend to the peak, you do it again. 
You burn most of the backpack and use the rest to build a hang glider. Lighter now, able to soar. 

That’s the evolution. 
You don’t have to throw everything away. 
You don’t have to start from zero. 
You just have to transform what you’ve built into something that fits where you’re going. 

Before you burn the fort, know the issue, know you are not alone, and start to look for the next mountain. 

Last week, I said I’d talk about Mission, Values, and Purpose, and I will. 
But this story unfolding in real time felt more important. 

When I texted him the phrase “burdened by your success,” he replied: 

“Those words really hit home. They summed it up perfectly.” 

My advice to him was simple: 
You’re standing at the top of your first mountain. 
There’s nowhere higher to climb, only a new mountain to see. 

Just knowing that next mountain exists is the first step. 
Identify the problem. Acknowledge it. 
Know you’re not alone. 
Then start seeking the path forward. 

Maybe next week, we’ll finally talk about Mission, Values, and Purpose. 
Or maybe The Man Who Couldn’t Chill will have taken his first step toward the second mountain. 

Either way, that’s where freedom begins. 

Reflection 

Have you ever felt burdened by the very success you once dreamed of? 
What would it look like to start climbing your second mountain?