Signs of landfall: Five practices for the middle passage

This article is the third part of a three-piece series. Here is part two.

What comes after the vortex

In our last article, we followed Ernesto Van Peborg from the Goldman Sachs boardrooms through the Atacama Desert and into what he calls the vortex. The Vortex is that frontier where transformation actually happens. Broke. Alone. Still economically dependent on the system you’re trying to change. Forced to price the priceless just to survive. The place where most people quietly decide it’s too hard and crawl back to the safety of the sinking bay.

But Ernesto didn’t go back. And in his account of what sustained him and what eventually shifted, I found something more useful than any polished transformation narrative I’ve encountered. Not a formula. Not a shortcut. Something closer to a logbook: honest notes from the passage, written by someone who made it far enough to sense the shore.

He writes about the Andean cosmovision, about Joanna Macy’s gifts of uncertainty, about Thich Nhat Hanh’s teaching that no mud, no lotus. The suffering and the beauty are not opposites. They are entangled forces. The mud does not prevent the lotus. It gives birth to it.

And then, slowly, something else emerges.  Out on the ocean, he writes, my ship has begun to sense signs of arrival. The smell of land carried on the wind. The cries of seagulls overhead. Fragments of vegetation drifting past the hull.

These are not metaphors for triumph. He’s careful about that. He still doesn’t know whether we will make it. That honest uncertainty, he says, hums beneath every decision and every brave attempt to reroute a civilization. What shifted wasn’t certainty. It was the recognition that he wasn’t drifting aimlessly. He was sailing toward something real.

What I’ve learned from asking hard questions

I spent thirty years in C-suites before I started asking the questions that eventually led me here. Five years of podcasting at the intersection of business and Planet Earth. More than 170 conversations with economists, scientists, lawyers, regenerative practitioners, and people who have walked exactly the path Ernesto describes.

Here is the pattern that has emerged most consistently through all of that. The people who make it through the messy middle are not tougher, smarter, or better-resourced than those who don’t. The difference is whether they have practices, deliberate and repeatable ones, that help them keep climbing when the ladder disappears into fog.

What follows are five of those practices. They won’t make it easy. Nothing makes it easy. But in my experience, they make it survivable.

Five practices for the middle passage

1. Name what you’re feeling. It’s geography, not failure.

The depression isn’t a sign that you’ve made the wrong choice. The loneliness isn’t proof you’re doing it wrong. The impotence — that crushing sense that nothing you do moves the needle — isn’t weakness. These feelings are the landscape of transformation. They are supposed to be here.

Ray Anderson had his spear in the chest. Ernesto called himself a plunderer of the earth and wept while reading Paul Hawken. The difference between people who make it through and people who don’t isn’t that some feel less pain. It’s that some learn to recognize the pain as a passage rather than a failure.

There’s a meaningful distinction between these two statements: “I’m feeling depressed because I’ve seen something true that most people refuse to see, and that isolation is real” versus “I’m depressed because I’m failing.” One is geography. One is judgment. Learning to tell the difference is, in my experience, one of the more important skills in this work.

2. Find your soulmates. But go looking for them.

Ernesto wrote that he blessed every step where soulmates appeared. What he didn’t say explicitly, but what I’ve found to be true, is that you have to actively seek them out. The frontier is lonely because you’re ahead of the curve. But you are not the only ship in those waters.

Here’s what I’ve noticed. The most magnetic thing you can do at the frontier is not perform successfully. It’s admit struggle. Reach out from the middle of the mess. Say: I’m in this. I’m not sure it’s working. Is anyone else feeling this? That honesty pulls the right people toward you. Not to rescue you. To climb alongside you.

3. Build capacity for uncertainty. It’s a trainable skill.

Joanna Macy describes uncertainty not as a curse but as a teacher, a threshold, a gift. Ernesto found his way to that through Andean cosmovision and Zen Buddhism. I’ve found mine through long walks, through conversations with people who could hold space for not-knowing without trying to fix it, through learning to make small commitments instead of grand visions.

The method matters less than the commitment. On this path, certainty is not available. What determines whether you survive is whether you’ve deliberately built the muscle to keep walking when the path disappears into fog. I couldn’t know if my work would change the world. But I could know that I would show up today and do the next right thing. That’s not resignation. It’s the work. 

4. When money runs out, let purpose become your currency.

Here’s the brutal economics of transformation: at first, there is no revenue. Only burn. Ernesto sold his Mini Cooper. I drained my savings.  Others mortgage their homes. The cash runs out fast, for all of us. Ernesto built frameworks, created knowledge pools, organized community efforts and learned that if you measure progress in dollars, you will conclude you are failing. Because by those metrics, you probably are.

The shift I’ve seen sustain people through this, and that I’ve made myself, is to a completely different set of measures. Not only did I hit my numbers, but did I show up with integrity? Did I learn something? Did I help someone see a different possibility? Am I moving closer to life’s patterns, or further away? 

These questions won’t pay the bills. You’ll still need to figure out the consulting gigs, the part-time work, the creative ways to keep cash flowing. But if you measure your transformation by the old metrics, you will quit. The new measures might very well reveal that you’re succeeding more than you’ve ever succeeded before. And THAT realization will make all your lifestyle changes feel so very worthwhile.

5. Watch for signs of landfall. They are there if you’re paying attention.

You cannot see the destination from the middle of the passage. But if you pay attention, you can sense it getting closer. For me, the signs showed up as conversations that used to be impossible becoming normal. People I didn’t know who were reaching out were aware of my work. Doors opening that I didn’t know I was knocking on.

These aren’t rewards. They’re navigation. They’re feedback that you’re heading in a direction that wants to meet you. But when you’re exhausted and discouraged, it’s easy to dismiss them as a coincidence or wishful thinking. So practice noticing. Write them down. These are your seagulls, your fragments of vegetation drifting past the hull. Land exists. You’re not lost. Keep rowing.

What the polished stories don’t tell you, but Ernesto does

Ernesto ends his account with something I find genuinely moving in its honesty. He writes that he would choose the same path again. Would he do certain things differently? Of course. He would have been kinder sooner. He would have unlearned faster. He would have sought soulmates earlier. But would he trade the desert for the suit? The strangeness of exile for the numbness of compliance?

No. Because the ladder is where he found out what mattered most.

I recognize that too. Thirty years in C-suites taught me a great deal. As did the long rehab from two strokes and a coma in 2015.  Ultimately, when we are forced to ask whether any of it is truly working for us, the answers we get back are worth the price we paid to get them. Five years of investigating the intersection of business and Planet Earth have convinced me that the sustainability movement is losing ground partly because it doesn’t speak the language of the people it most needs to reach. And all the honest conversations with people like Ernesto have convinced me that the most important thing we can do for that movement right now is stop sanitizing the middle of the story.

The climate crisis is not waiting. The biodiversity collapse is not waiting. And right now, in boardrooms, sustainability departments, and startup offices around the world, people are giving up in year five or year seven, concluding they have failed, when they have actually just arrived at the hardest part.

You are not alone on the ladder

We are all living with the unintended consequences of decisions collectively made over the last hundred years. A do-over is a fantasy. The only thing available to us now is a do-better. And that do-better, to mean anything, must be in the highest good for all.

I’ve come to see that that requires people willing to stay in the messy middle long enough for momentum to build. People who name the depression rather than interpret it as failure. Who seek soulmates rather than wait for rescue. Who build capacity for uncertainty as deliberately as they build any other skill. Who redefine what success looks like when the old metrics stop working. And who watch carefully, for the signs that land actually exists.

Ernesto found hundreds of change-makers at the frontier. People filled with pure intention and guided by purpose, forming what he calls an emergent field. A paradigm shift. Slow and fragile, but real.

I’m betting on the same thing. And I’m betting there are far more of us in these waters than the sanitized success stories have ever let on.