Ride the Impossible

Surfing Montara, CA

“Do not think that what is hard for you to master is humanly impossible; and if it is humanly possible, consider it to be within your reach.” — Marcus Aurelius

Marcus Aurelius Antoninus, often regarded as the last of the Five Good Emperors of Rome, was born Marcus Annius Verus in Rome around 121 CE and was educated within an intellectual environment that placed extraordinary emphasis on Stoic philosophy. From a young age he was deeply influenced by these teachings and adopted a lifestyle that reflected the alignment of personal conduct with philosophical reflection. After being adopted by Emperor Antoninus Pius, Marcus Aurelius eventually ascended to power as co-emperor with Lucius Verus in 161 CE, marking the first time in Roman history that the empire was formally governed by dual rule, a political arrangement that emerged at a moment when Rome faced extraordinary pressures both within and beyond its borders.

The period of his reign unfolded under enormous strain, as the Roman Empire confronted wars against the Parthian Empire in the East and Germanic tribes along its northern frontier, while a devastating plague swept across the empire, weakening its armies, disrupting trade, and creating social instability throughout the provinces. Amid these challenges, Marcus Aurelius maintained a habit of writing personal reflections never intended for the public and later compiled as Meditations. These writings reveal a leader constantly reminding himself of the Stoic principles he believed were necessary.

“The impediment to action advances action. What stands in the way becomes the way.” — Marcus Aurelius

His reflections continue to resonate because they address a difficulty that appears repeatedly throughout human life, particularly during moments when individuals step into roles or responsibilities that exceed what they previously believed themselves capable of managing. The challenge in these moments is not merely the effort required to learn something new, nor even the labor associated with mastering unfamiliar systems, but rather the internal difficulty of believing that what is being asked of us is genuinely possible.

I encountered this kind of threshold when I began building the nonprofit organization Kaunalewa, which emerged from an effort to explore whether the community on the island of Kauaʻi could acquire and restore the abandoned Kekaha Sugar Mill. The property carried the legacy of plantation agriculture and the environmental burdens that accompany decades of industrial use. If the community were to reclaim the land, the work would require navigating environmental remediation, land-use policy, public financing, and long-term stewardship—layers of regulatory and institutional complexity that few individuals attempt to navigate alone.

To access funding through the State Legislature’s Special Purpose Revenue Bond program, the project required a nonprofit organization capable of receiving and managing those funds, which led to the formal creation of Kaunalewa in 2019. This work represented an entirely new landscape for me, as it required engaging directly with state legislators, federal agencies, and environmental policy frameworks far removed from the technology environments in which I had previously built my career.

When I first described the project to a friend who led a large nonprofit organization in California, he listened carefully, then leaned back in his chair and explained that the scale of what I was proposing would normally require a large team and significant capital. Nearly everyone responded the same way: the vision was admirable, but the scale appeared overwhelming. Yet the history of every enduring endeavor suggests something different. Structures that appear monumental from the outside are almost always the result of patient accumulation over time rather than a sudden triumph.

During that period, I found myself reflecting on the nature of ambition, particularly as described by the poet and philosopher David Whyte, who writes in Consolations that ambition allows us to direct a beam of attention toward a particular corner of the future.

“We may direct the beam of ambition to illuminate a certain corner of the future world.” — David Whyte

Ambition can reveal possibilities, yet it can also distort perspective if left unchecked. The question confronting me was not simply whether the project could succeed, but whether I was prepared to commit myself to a form of work that would likely unfold across many years.

My own experiences in technology had already demonstrated how unpredictable the path of ambition could be. After the collapse of Inktomi during the dot-com bust, I moved from one struggling company to another, eventually spending eight months at Webvan, where I had been hired to clean up financial systems and help guide the company through its final stages.

“Failure became a quiet classroom for ambition.”

During those months, I watched the once energetic workplace slowly empty as employees packed their belongings and left. Delivery drivers were laid off. Hallways that had once buzzed with optimism became silent rows of empty cubicles.

In the years that followed, I continued consulting with companies facing similar circumstances, gradually developing a reputation for arriving during moments of organizational crisis when systems needed to be stabilized and transitions carefully managed. At times the work felt almost janitorial, as though my role was simply to sweep up after the final act had concluded.

“A true vocation calls us beyond ourselves.” — David Whyte

When the opportunity to pursue the Kekaha Mill project appeared, those memories returned with intensity because I understood that the work ahead would be riddled with unpredictable failures, and that success, if it came at all, would remain a distant vision requiring the patience of long-term civic and environmental restoration

The work demanded the same instincts builders rely on in business—persistence, resourcefulness, and the willingness to move forward without guarantees—but applied them to a landscape where the outcome would affect communities rather than shareholders.

“While I am often embarrassed to admit to being a businessman—I’ve been known to call them sleazeballs—I realize that many activists could learn some of the skills that businesspeople possess.” — Yvon Chouinard, Patagonia Founder

Years passed more quickly than I expected, and eventually I realized that seven years had elapsed since the organization's formation. During that time, I had accumulated knowledge I could not have imagined when the work first began, and my writing and advocacy began influencing conversations across the state about environmental justice, cultural preservation, and water.

Looking back, the early stages of any ambitious undertaking often appear impossible from the outside because observers see only the scale of the challenge, not the rhythm that develops once the work begins.

“What stands in the way becomes the way.” — Marcus Aurelius

At first, the problems feel overwhelming because everything is unfamiliar. Over time, the unfamiliar becomes navigable. Patterns emerge. Entrepreneurs often describe this moment as connecting the dots, though in reality, we are laying the dots ourselves. One decision leads to another, and momentum begins to build.

I once worked with someone who never celebrated after reaching a milestone. For years, I did not understand why, until I realized that his restraint came from an understanding of momentum. When progress accelerates, pausing too long can interrupt the very energy that created it.

“Ambition takes us toward the horizon, but never over it.” — David Whyte

The closest analogy I can offer is surfing. When a surfer catches a wave, commitment must be complete because the energy of the wave is already moving forward. If you bail too early, you miss the ride entirely. If you hesitate, lose focus, you wipe out. But if you commit at the right moment, the same wave that looked intimidating from shore becomes something that carries you.

The work with Kaunalewa eventually began to feel like that wave. I did not want to step away without discovering what the effort would require.

Builders see the word impossible differently. Not as a final judgment, but as an invitation to test whether the boundary is real.

“Sometimes when I’m feeling really down about something, I remember a metaphor. It always reminds me of who we are and what we are trying to do. On one side of the door is all of the turbulent present and all of the turbulent past: all the passions and emotions, ups and downs, victories and defeats. On the other side, we don’t know. We can have our opinions about what it might be, but I believe it might be, and can be, a more benign future.”

— Brock Evans, 2008 Tools Conference

Take the wave, ride the impossible.

Sincerely,

Mayrose

Mahalo, Tommy Peirucki (pineapplesunrise.com)