When the suit becomes a skin you can’t take off

This article is the second part of a three-piece series. Here is part one.

The smartest money in the world

For those who know the language of money, certain phrases carry weight. Selling investment strategies to the Goldman Sachs Partners Fund is one of them. This isn’t pension capital or retail investment. It’s the partners’ own money. It’s the so-called smartest money in the world, and the due diligence is merciless. Only a handful of pitches ever make it through.

Ernesto Van Peborg made it through. He went on to become general partner in an AIG fund under Hank Greenberg, back when AIG was an empire. He dined in rooms where Greenberg and Henry Kissinger shared cigars and strategy. He wore the Armani suit, the red power tie, the suspenders, all the badges of belonging, as he’d later call them, that were also a noose.

He was, in his own words, a celebrity of capital. First class flights. Marble offices that smelled of leather and excess. Overseeing deals that reshaped industries. Like the most modern cheese plant in Latin America, marketing rights for football clubs, leveraged buyouts that moved billions. In his own words, he was surfing the crest of neoliberalism’s greatest wave.

Only later would he learn the tide was mastering him.

The hollowing that success can’t fill

I recognize this part of his account. Not the Goldman Sachs rooms. (My C-suites looked different!) But the pattern underneath it is familiar to anyone who has led organizations at a serious scale: the more the external markers of success accumulate, the more something interior begins to drain away. You keep performing the role. You keep hitting the numbers. And somewhere in the middle of it, you lose the thread of why any of it matters.

Ernesto describes it as inhabiting a snake’s body that had outgrown him. Tight. Toxic. Crawling with small infections of vanity and fear. The only way out was the way snakes have always shed. Crawling into darkness alone, pushing against rock and shadow until the old sheath tears.

From the outside, it looked like success. From the inside, however, it was all collapsing.

So he stepped out of the system. He did what many of us in this community have done or are contemplating. He walked away from the machine he’d helped build, naively believing, as he now admits, that the very tools and habits that had made him successful could also remake the world.

Seven marathons, and what they didn’t answer

The hollowing followed him out of the boardroom. He ran, later acknowledging he was probably running away from himself, through rainforest and mountains, two hours of sleep a day across 300 kilometres in New Zealand. Then came the desert.

Seven days. Seven marathons. 250 kilometres across the Atacama, carrying everything on his back. A marathon each day, and each day a stripping down of self. The desert’s vast hollowness mirrored the hollowness within. Silence absolute. Horizon unbroken. Sky merciless.

By the end, something had shifted. He emerged with what he calls a raw new clarity -- a fragile, pure intention to discover his purpose. The old skin was gone. The problem was what waited on the other side.

Here’s what the desert couldn’t tell him, what I learned decades ago and what I’ve heard echoed by every serious change-maker I’ve interviewed over the last five years. Leaving the system is NOT the hardest decision. We imagine it is. Walking away from the title, the paycheck, the identity.  ALL of that FEELS like the ultimate leap. But it’s only the first step.

Because most people who leave simply build another box. The consultant box. The entrepreneur box. The startup box. Each dressed in the language of freedom, yet bound by the same invisible walls. You may change the furniture, but you’re still living in a room designed by the system you thought you’d escaped.

The multi-polar traps we’re all caught in

What Ernesto encountered next is something complexity theorists have a name for: multi-polar traps. The situation where each actor, pursuing their own short-term interest, drives the whole system toward collapse.  Even though none of them actually wants that outcome. This is the tragedy of the commons, amplified across every domain simultaneously.

Nations are trapped in an arms race. Companies are trapped in a competition that strips resources. Consumers are trapped in cycles of status and debt. No single actor designed it. Everyone is pulled into it. And this meant, as Ernesto and so many of us have come to understand, that the solution could not, can not, will never be a simple individual escape. A shinier box, a more virtuous business, a single committed leader. None of it was sufficient.

The problem requires systemic change. And systemic change requires two things that are both in desperately short supply: the inner capacity to hold paradox, uncertainty, and pressure without collapsing into fear AND the practical tools to actually navigate complexity. Systems governance. Regenerative economics. Adaptive technologies. A completely different lens on what success means.

This is where Ernesto’s account moves from personal story to something that cuts closer to home for anyone doing serious sustainability work. Because this is where I’ve found myself, too. And based on the conversations I’ve had with economists, scientists, and practitioners over five years of podcasting and playing in this space, it’s where most of us are.

The frontier where everyone is searching for money

Ernesto sold the trophy of his investment banking years.  His Mini Cooper.  Then he discovered what most people who leave the old system discover. If you haven’t yet found out who you are, there is no revenue. There is only burn.

So, he built frameworks for wellbeing projects. Created knowledge pools for companies. Organized community efforts. Tried to stitch purpose into the fabric of the old world. And each attempt revealed the same uncomfortable truth. This system cannot be healed by the mindset that built it. As Einstein warned, you cannot solve a problem with the same thinking that created it.

And then came the cruellest irony of the frontier. To resist the old system, you find yourself trying to price the very things that have no price. Soil. Water. Breath. Love. You are forced to put numbers on what is beyond value. Because that is the only language the old system speaks. You try to stop the machine by using the machine’s own levers.

Meanwhile, unless you are a millionaire, you still depend economically on the system you are trying to change. Which makes you a participant in the very processes you want to reverse. Radicalization isn’t possible for most of us. So you comply with parts of the system even as you try to shift it. And in that contradiction lives a very particular kind of exhaustion.

What the grief is telling you

Ernesto travelled to Svalbard, where the Arctic is warming six times faster than the global average, to watch the ice shelves bleed into the sea. He went into the Ecuadorian Amazon to see rainforest torn open by oil and cattle. Not as a tourist. As a witness. A way of saying to himself that this is real and this IS happening.

When he returned and tried to reawaken others with what he’d seen, boardrooms barely registered it. Eyes flickered toward him, found a category (ecologist, activist) to box him into, and the conversation floated back to golf handicaps and quarterly earnings. The unravelling of life itself was acknowledged for a heartbeat and shelved.

He has a word for what followed. He borrows it from Australian philosopher Glenn Albrecht: solastalgia. The homesickness you feel while still at home. It’s when the familiar world is unravelling before your eyes. Not nostalgia for a distant past. The grief of watching the present collapse.

Was he depressed? Yes, he writes. Because he had lost the sense of belonging. And what deepened the ache was the impotence.  That thriving force within him that had always believed he could change things, now turned into a weight too heavy to carry alone.

Here’s what I’ve come to believe about that depression, based on my own experience and everyone I’ve interviewed who has walked this path: it is not a sign that something has gone wrong. It is a compass. It reminds you that you are genuinely bound to these rivers, these forests, and these creatures. That the unravelling of their lives is also the unravelling of ours. Grief at that scale is not dysfunction. I’ve come to see it as an appropriate response.

The ladder is steep. Others are on it

Once you’ve seen through the veil, Ernesto writes, you cannot put it back. Once the paradigm collapses in your mind, you cannot reassemble it. You live in a new reality that most others refuse to recognize. And that is where depression and anxiety find fresh fuel.  It comes not from the grief of what is being destroyed, but from the denial of others. Their unwillingness to see becomes a kind of exile. You are not rejected outright. You simply no longer belong where you once belonged.

This is the frontier. Broken. Alone. Still economically dependent on the system you’re doing your level best to change. Forced to price the priceless just to eat. The ladder is steep. Progress is invisible. And this is precisely where most people give up.  It’s where most of us end up concluding it’s too hard, too lonely, and too steep.  And most crawl back to the bay even though they know it’s sinking.

But here is what Ernesto discovered at the frontier, and what keeps me going when I encounter my own version of this darkness. The frontier has a secret. You are not alone on the ladder. There are hundreds, maybe thousands of others with you.  Each digging in their own place, each rowing toward the same unseen continent. And slowly, as you climb and seek them out, something begins to shift.

In our third and final article, we arrive at what Ernesto calls the signs of landfall.  And we dig into five practices that I’ve found, both personally and professionally, can help you keep climbing when the ladder disappears into fog.