The Philosophy of Adventure: Tom Preston-Werner’s Declaration Against the Ordinary Life
Tom Preston-Werner’s often-quoted reflection on mortality and meaning captures something fundamental about his approach to life and entrepreneurship: a deliberate rejection of safety in favor of experience and growth. This quote emerged from Preston-Werner’s own journey as a software developer and founder, spoken during various interviews and talks throughout his career as he reflected on what drives human purpose. The statement reflects a worldview shaped by his deep immersion in technology, startups, and the philosophy of pushing boundaries—a perspective that gained particular resonance in the early 2010s as discussions about meaningful work and the “startup lifestyle” permeated popular culture. For Preston-Werner, this wasn’t merely motivational rhetoric; it represented a genuine conviction that animated his business decisions, his abandonment of promising opportunities, and his willingness to pursue uncertain ventures. The quote speaks to a generation increasingly questioning whether traditional notions of security and stability actually lead to fulfillment, making it surprisingly relevant nearly fifteen years after it first circulated widely.
Preston-Werner’s background helps explain why this philosophy became so central to his identity. Born in the 1980s in Iowa, he grew up during the digital revolution’s adolescence, when the internet was still transforming from novelty to necessity. He discovered programming relatively early and became utterly consumed by it—the kind of person who spent his teenage years not just learning code but experimenting with it, building things, breaking things, and understanding how systems worked from first principles. This wasn’t the path of someone being pushed into technology by parents or economic pressure; it was genuine passion. He taught himself not just programming languages but the underlying philosophy of how to think computationally, how to solve problems through iteration, and how to build systems that could scale. This self-directed learning, which bypassed traditional computer science education at least initially, instilled in him a certain intellectual independence and a willingness to trust his own judgment over conventional wisdom.
What many people don’t realize about Preston-Werner is that he spent years working relatively conventionally before finding his breakthrough. He worked as a software developer at various companies, including a role at Powerset, a semantic search company that was eventually acquired by Microsoft. While these positions paid well and provided stability, they increasingly felt constraining to someone with his entrepreneurial impulses. The real turning point came in 2008, right as the financial crisis was beginning to reshape the American economy. Most people were retreating into conservative positions, tightening their belts, and seeking the safety of established employment. Preston-Werner did the opposite. He left his job at Powerset to start GitHub, a platform for version control and collaborative software development. In doing so, he was essentially betting that the world needed a better way for programmers to share code, collaborate, and build software together—and that despite the collapsing economy, people would find value in what he was building. This decision to launch a startup during the worst economic downturn since the Great Depression was, in his own terms, choosing adventure over safety.
GitHub’s rise proved prescient and transformative, becoming one of the most important platforms in modern software development. The company grew from Preston-Werner’s garage into a billion-dollar enterprise that Microsoft acquired in 2018 for $7.5 billion. Yet what’s fascinating about Preston-Werner’s career trajectory is that he didn’t simply ride GitHub’s success to retirement. Instead, after leaving GitHub (a departure that came after some internal conflict and cultural challenges), he continued to pursue new ventures and philosophical explorations. He became an investor, a philanthropist focused on scientific research and rationality, and founded organizations like the Human Longevity Project. This pattern of movement—building something significant, moving on before becoming comfortable, starting anew—perfectly embodies his stated philosophy about adventure. He could have remained at GitHub indefinitely, accumulating wealth and power within an increasingly stable institution. Instead, he chose to remain in motion, chasing new intellectual and entrepreneurial challenges.
The quote’s cultural impact has been particularly pronounced within startup and technology communities, where it serves as a kind of philosophical north star for the industry’s value system. It gets quoted in entrepreneurship podcasts, startup pitch decks, and motivational social media posts as a rallying cry against the supposed mediocrity of conventional life. However, this popularization sometimes obscures the complexity of what Preston-Werner was actually articulating. He wasn’t celebrating recklessness or glorifying unnecessary risk-taking in a toxic way. Rather, he was expressing a belief that a life oriented entirely around avoiding pain, failure, and uncertainty produces a kind of existential anemia. The quote resonates because it touches on something most people intuitively feel: that safety without purpose, and comfort without growth, leaves something vital unfulfilled. In an era of increasing economic anxiety and the paradoxical coexistence of unprecedented comfort with widespread anxiety, Preston-Werner’s declaration feels almost rebellious—a suggestion that the proper response to mortality isn’t to build walls against risk but to say yes to meaningful challenge.
What gives this philosophy particular weight in Preston-Werner’s own life is his genuine engagement with existential questions beyond mere startup cheerleading. His philanthropic work, particularly his donations to scientific research exploring aging and human longevity, suggest that his reflection on mortality isn’t abstract philosophizing but reflects real encounters with the finite nature of existence. These investments in longevity research represent a kind of both-and thinking: yes, life is finite and should be lived adventurously, but also, extending healthspan and exploring what makes a long life worth living are scientifically crucial endeavors. This nuance suggests