This first-person narrative originates from an in-depth conversation with Jay Gengelbach, a 41-year-old software engineer who was born in Boulder, Colorado, and now resides in Canada. What follows has been thoughtfully refined and elaborated for clarity, length, and narrative cohesion.
Jay began his professional journey immediately after earning his college degree, joining Google in 2006 as a young and enthusiastic software engineer. At the time, landing a role at such a globally celebrated company felt like both a personal triumph and a public badge of honor. Simply being able to introduce himself as a Google employee opened doors in conversations and lent him an aura of distinction—one that reflected both his hard-earned technical competence and the broader cultural fascination surrounding Silicon Valley success stories.
He dedicated roughly twelve years of his career to Google before seeking a new challenge within its parent corporation, Alphabet. In 2018, Jay transitioned to Verily, Alphabet’s life sciences and health technology subsidiary. During his six-year tenure there, his career continued to advance, and his compensation eventually reached an impressive $700,000 per year. Yet, despite this financial success, Jay began to sense an erosion of personal satisfaction. By mid-2024, he could no longer ignore a persistent feeling of disengagement. He made the difficult and deliberate decision to resign, choosing authenticity and peace of mind over financial security—a decision that initially terrified him but has since proven deeply rewarding, both emotionally and financially. Over the following year, as the dust settled, he came to see that stepping away from the comfortable predictability of Big Tech had been an act of renewal.
Every year, around this same season, Jay notices how people tend to reflect on their professional paths—questioning whether their work still excites or fulfills them, and whether comfort has dulled their appetite for growth. In that spirit, Business Insider spoke with several individuals who had also departed from prestigious, high-paying positions in search of a new sense of purpose, whether that meant founding companies, exploring different industries, or reimagining what professional success could mean. Their shared stories reveal universal truths: that walking away from a “dream” job requires courage, that doubt is inevitable, and that the risk of change, while unsettling, can yield immense personal growth and a more intentional relationship with one’s career.
In Jay’s case, his 18 years in Google’s sphere came to define a substantial chapter of his life. Reflecting on that period, he describes how exhilarating it had been at first: the creativity, the scale of the projects, and the culture that once felt utopian. Google was renowned for its extravagant perks—lavish cafeterias offering gourmet food, on-site nap pods for mental rejuvenation, and occasional spontaneous festivities that seemed to erase the line between work and leisure. He recalls walking into the campus one afternoon and encountering a luau-themed lunch, complete with decorations and tropical food, all orchestrated simply to elevate the team’s morale without any formal occasion. At times, Google even issued cash bonuses of $1,000 during the holidays—an almost surreal gesture that reinforced the company’s image as both generous and forward-thinking.
Initially, Jay’s technical responsibilities involved maintaining the stability and performance of Google’s core infrastructure—software that ensured the platform operated smoothly at an extraordinary scale. After two years working in California, he transferred back to his home state of Colorado, continuing the same type of work for another two years. Although he admired Google’s innovative culture, the work itself eventually began to feel repetitive. The constant exposure to the same type of challenges eroded his enthusiasm, and bouts of burnout began to creep into his routine. Seeking new energy, Jay shifted to Google’s payments team, where he spent the next four years developing systems that facilitated secure and seamless transactions across billions of users. Another four-year chapter followed—this time on the Google Now team—where he embraced managerial responsibilities. It was here that he discovered an important truth about himself: after about four years in any given role, his curiosity waned, and the yearning for novelty resurfaced.
When he later accepted a managerial position, Jay found that the isolation of leadership presented its own distinct challenges. In 2018, the opportunity to join Verily seemed like a promising evolution. The company’s mission—to enhance healthcare through technology—resonated with his intellectual curiosity and ethical values. Rising through the ranks, he eventually became an engineering director, leading teams and projects that blended software innovation with human well-being. Yet, over time, the emotional toll of leadership, especially during the pandemic and following rounds of layoffs, began to weigh heavily. As a manager, he was expected not only to deliver results but also to keep his team motivated amid uncertainty. The role demanded resilience and constant optimism, traits that became difficult to sustain in an environment clouded by anxiety and instability.
Perhaps the most painful realization came when Jay noticed that his social environment at work had quietly disintegrated. The easy camaraderie he once shared with colleagues was replaced by cautious professionalism. Lunch invitations that once emerged from genuine friendship now carried an undertone of strategic networking. The loneliness of management—the quiet distance that separates leaders from those they lead—became unbearable. For the first time, Jay admitted to himself that he no longer had true peers in the workplace.
Although he briefly considered returning to Google, a closer look at the evolving atmosphere there convinced him otherwise. Massive layoffs in 2023 had cast a visible shadow across the tech industry, altering the tone and morale of even the most resilient teams. The culture of abundance and optimism that had once defined Big Tech seemed to have shifted toward caution, anxiety, and self-preservation. Realizing this, Jay began to see a fork in the road. For nearly two decades, he had managed to harmonize personal happiness with professional and financial prosperity. Now, for the first time, the two were diverging, and he had to decide which path to follow.
With encouragement from his wife and valuable guidance from his therapist, Jay finally chose to resign from Verily in mid-2024. The decision felt both frightening and liberating. He was acutely aware of the uncertain job market and the potential drawbacks of leaving such a lucrative position. However, prudent financial planning had equipped him with enough savings to sustain his family comfortably for at least a year, even without new employment. The idea of earning substantially less was daunting—after all, his last compensation package reached nearly $700,000 annually—but the fear of remaining unfulfilled proved even stronger than the fear of losing income.
Before beginning his job search, Jay carefully outlined the characteristics of what he considered his “ideal role.” He envisioned a position that combined technical depth with moral purpose, ideally as an individual contributor rather than a manager, in an industry that contributed positively to society. His goals extended beyond salary and status—they now included intellectual stimulation, autonomy, and balance.
By October 2024, his search led him to a remote role as a distinguished engineer at an insurance company, which provided stability and a renewed sense of engagement. However, a few months later, in January, he accepted a new opportunity as a software engineer at Vercel—a fast-growing infrastructure company whose mission is to empower businesses by improving web hosting and development experiences. The company’s flexibility also enabled him to fulfill a personal dream: relocating his family to Canada, where they finally settled in July 2025. For Jay, this move represented more than a change of scenery—it symbolized a reclamation of autonomy and alignment between his personal life and career values.
Working at Vercel reawakened his enthusiasm for solving complex engineering problems. Unlike the managerial work of previous years, his current role allowed him to focus deeply on technical innovation and creative problem-solving. The faster pace of a smaller company, coupled with the tangible impact of his contributions, rekindled the excitement he had once associated with coding and creation. For the first time in years, he felt intellectually alive again.
Still, leaving Big Tech required difficult financial adjustments. Where once his lifestyle had inflated to match a high salary—with a large home, a private pool, and the comfort of frequent vacations—Jay and his family deliberately scaled back. Downsizing in Canada reduced both expenses and stress, allowing them to live more intentionally and with less attachment to material comforts. He understood that smaller companies might offer reduced bonuses or equity compared to corporate giants, but the trade-off felt worthwhile.
Interestingly, not long after his transition, Vercel announced a significant funding round that tripled its valuation to approximately $9 billion, substantially increasing the potential value of its employee equity. Although Jay’s shares were still unvested and non-liquid, the development subtly reaffirmed that his decision to leave Big Tech was not as financially reckless as it once seemed.
In retrospect, Jay now sees his journey as a vivid reminder that wealth alone does not guarantee happiness. The experience taught him that even generous salaries can become a form of captivity—what many in the industry call the “golden handcuffs.” At one point, he realized that despite earning far more than he needed, he continued chasing financial growth simply out of fear of what life would look like without it. Breaking free from that illusion has allowed him to rediscover fulfillment on his own terms. Today, Jay feels balanced, intellectually engaged, and genuinely content. He has proven to himself that while money can provide comfort and opportunity, it cannot replace meaning, purpose, or the quiet joy of waking up each morning excited about what’s ahead.
Sourse: https://www.businessinsider.com/quit-tech-job-take-risk-money-happiness-lesson-2025-11
