Reflections on Trauma, Achievement, and the Search for Meaning in Tech

Outsiders with Something to Prove: How Childhood Adversity Fuels Achievement

There’s an old saying that some of the deepest scars can forge the strongest steel. In the high-octane world of startups and tech, that idea takes on a profound, if unsettling, truth. I have spent years navigating the relentless pursuit of innovation, a journey propelled by both ambition and a need to prove something to myself. Yet, as I’ve come to learn, the very drive that fuels breakthrough achievements can also leave a lingering emptiness—a hollowness that no amount of accolades can ever truly fill.

The Hidden Edge: When Adversity Becomes Fuel

In a Business Insider article, Doug Leone, the managing partner at Sequoia Capital, shared a provocative insight: he seeks out “spiky founders”—those individuals who, because of what might be colloquially labeled “daddy issues” or early familial neglect, have an insatiable need to prove themselves. I remember reading his words and feeling a strange resonance. It seemed to capture a truth I had wrestled with for years—the sense that personal hardships can ignite an urgency, a relentless drive to overcome the odds.

For many founders, including myself, the past is not merely a series of memories—it is the crucible in which our identities are forged. Growing up gay in a small, rural, and conservative community in Maine added a unique and challenging dimension to that crucible. In an environment where acceptance was sparse and my very identity was questioned, I constantly battled feelings of inadequacy and isolation. Every day, I was reminded of my otherness, and the unspoken message was clear: I had to work twice as hard to be seen, to be valued, to belong. In the fast-paced tech world, where innovation is celebrated and measured in breakthrough achievements, this drive became both a powerful motivator and an ongoing burden. It is a force that propels me forward, yet also reminds me of a past that never fully disappears.

Reflections from McKinsey: Insecure Overachievers in a High-Pressure Environment

After college, I spent several formative years at McKinsey & Company—a place renowned not only for its strategic rigor but also for its relentless pursuit of excellence. At McKinsey, I discovered that the drive to excel was as much about quelling deep-seated insecurities as it was about solving complex business challenges.

Within the Firm, we often joked about being “insecure overachievers.” The culture was engineered to identify and nurture individuals who felt the constant pressure to prove themselves—a mindset that resonated deeply with many of us, myself included. The structured, almost Pavlovian cycle of achievement we experienced reminded me starkly of my school days: clear, measurable goals and immediate rewards. Yet, once the applause faded, I was left confronting the same internal void—a persistent reminder that external markers of success could only do so much to assuage an inner need for validation.

Image courtesy of gpt4o (ChatGPT)

Working at McKinsey provided invaluable lessons. I gained exposure to diverse challenges, built a formidable network, and honed a skill set that has propelled my career forward. But it also reinforced a crucial truth: while external accolades and a prestigious brand can open doors, they are no guarantee of inner fulfillment. In that environment, every project success was a small pat on the back, yet it also set the stage for the next performance, trapping us in a cycle that often blurred the line between genuine passion and the compulsive need to prove our worth.

This experience was a microcosm of a broader trend—not just in consulting, but across investment banks, big tech, and startups—where the promise of external validation can both empower and confine. It became clear that the challenge wasn’t simply achieving more; it was learning to step beyond that ingrained need for continuous external affirmation, seeking instead a deeper, more sustainable source of self-worth.

Outsiders by Nature: A Different Kind of Resilience

On the 20VC podcast, George Sivulka, the Co-Founder and CEO of Hebbia, offered a compelling perspective on why so many successful entrepreneurs seem to emerge from the fringes. He categorized founders into groups that, by definition, have always felt like outsiders—LGBT individuals, those with a rough childhoods, and adoptees. His words struck a chord with me, as they mirrored my own experiences of always having to carve out a space in a world that often felt indifferent or even hostile.

Notably, this phenomenon is also well-documented among gay men. In a New York Times opinion piece titled The Best Little Boy in the World, That's Me, researchers John Pachankis and Mark Hatzenbuehler substantiate what’s known as the “Best Little Boy in the World” hypothesis. Originally proposed in 1973 by Andrew Tobias (writing under a pseudonym), this hypothesis suggests that young, closeted men deflect attention from their concealed identities by overinvesting in universally recognized markers of success—academic excellence, athletic prowess, elite employment, and more. This compensatory behavior offers them a semblance of self-worth to counterbalance the burden of secrecy. In a world where being different often comes at a high personal cost, overachievement can serve as both armor and affirmation.

It isn’t hard to see why figures like Tim Cook and Sam Altman have harnessed this outsider energy, channeling personal struggles into formidable professional success. Their journeys, along with those of many immigrant founders and adoptees, illustrate a recurring theme in our industry: the transformative power of resilience born from adversity.

The Science Behind the Scar: Evidence of Adversity and Achievement

This isn’t just anecdotal. In an illuminating article for Inc., Jessica Stillman examines a study of 400 super high achievers—individuals so influential that at least two biographies have been written about them. The findings were as striking as they were sobering: 75% of these exceptional people had experienced severe childhood adversity, such as the loss of a parent, dire poverty, or abuse. Stillman explains:

“Most kids who experience this suffering don’t grow up to be CEOs or TV stars; instead, they often live lives stunted by their early experiences. But in a minority of cases, these early struggles teach extreme resilience that leads to incredible achievement.”
Read more on Inc.

Image courtesy of gpt4o (ChatGPT)

This research underscores a difficult truth: while trauma is never something to be celebrated, in rare instances it can ignite a spark of resilience that propels individuals to remarkable heights. It’s a double-edged sword—the very forces that drive us to succeed can also leave us grappling with a sense of isolation and disconnection, long after the initial battles have been fought.

When Success Feels Empty: Reflections from the Top

I find myself reminded of a candid blog post by the Loom CEO and co-founder, Vinay Hiremath, titled “I Am Rich and Have No Idea What to Do With My Life.” In his raw, unfiltered narrative, he lays bare the profound emptiness that can follow after achieving what many of us spend our lives chasing. Despite the external trappings of wealth and success, he confesses to feeling lost—an experience that resonates deeply with anyone who has ever tied their sense of self to the next big achievement.

Similarly, even people like Elon Musk have shared glimpses of the relentless pressure that comes with a drive forged in early hardship. In Walter Isaacson’s biography of Musk, we learn of the personal demons and the ever-present internal pressure that fuel his groundbreaking ventures. These accounts remind us that the price of success can be steep—a cost measured not only in sleepless nights and constant pressure, but also in the struggle to find genuine fulfillment beyond the next milestone.

My Journey: The Weight and the Wonder of Achievement

As I reflect on my own journey, I can’t help but acknowledge the complex interplay between drive and discontent. In the early days of my career, every success was a validation—a proof that I was finally overcoming the doubts and insecurities of my past. The accolades, the recognition, the very act of breaking new ground in tech—it all served as a potent antidote to the feelings of inadequacy that had once defined me.

Yet, as the initial rush of achievement began to fade, I encountered a truth that many of us in tech eventually face: external validation, while exhilarating, is a fickle source of self-worth. The very achievements that once felt like a shield against a troubled past began to reveal their limitations. There came a point when I realized that each success was merely a temporary salve, and the deeper yearning for meaning could not be quenched by accolades alone.

The cycle of relentless achievement—driven by the need to prove oneself—can leave us perpetually chasing the next high, never quite able to find the lasting satisfaction we crave. This is a familiar narrative in our industry, where the pressure to innovate and outperform is constant. For me, the challenge has been to redefine what success means on a personal level. It’s a journey of transforming external milestones into internal growth—a process of learning to value the work itself, the passion for innovation, and the intrinsic rewards that come from building something meaningful.

Beyond the Shadows: Finding a Path to Inner Fulfillment

Ultimately, the stories of resilience—from the insights of Doug Leone and George Sivulka, to the hard data on childhood adversity, to the reflective admissions of leaders like the Loom CEO—point to a fundamental truth: while early hardships can forge an unyielding drive, true fulfillment comes from within. The task before us is not to glorify trauma, but to acknowledge its impact and to find ways to transform the scars into sources of genuine strength.

For me, that means embracing a new paradigm—one where success is measured not solely by what is achieved, but by the depth of passion, the quality of our relationships, and the meaningful contributions we make to the world. I strive every day to shift the focus from external validation to internal fulfillment, reminding myself that my worth is not defined by a series of milestones, but by the values I hold and the impact I create.

In sharing these reflections, I hope to spark a conversation among fellow founders, technologists, and anyone who has ever felt the weight of expectations. May we learn to honor our pasts—not as a source of perpetual burden, but as a wellspring of resilience that guides us toward a richer, more balanced sense of purpose. In the shadows of our early struggles, there is also the promise of a light that comes from knowing who we truly are, beyond the relentless chase for validation.

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Sources

• Business Insider. “Sequoia’s top VC Doug Leone wants to invest in tech’s spiky founders.” April 2022. Link

• Stillman, Jessica. “75 Percent of Super High Achievers Come from Troubled Families. Here’s Why.” Inc. Link

• Sivulka, George. “George Sivulka, Co-founder & CEO of Hebbia | 20VC Podcast.” YouTube. Link

• Isaacson, Walter. Elon Musk, HarperCollins. Link on Amazon

• Vinay Hiremath’s Reflection. “I Am Rich and Have No Idea What to Do With My Life”

• Pachankis, John & Hatzenbuehler, Mark. Referenced in The New York Times, “The Best Little Boy in the World, That’s Me”, May 2013.