The Philosophy of Adventure: Tom Preston-Werner’s Declaration Against the Ordinary Life
The Origins of This Adventurous Quote
Tom Preston-Werner’s often-quoted reflection on mortality and meaning captures something fundamental about his approach to life and entrepreneurship. He deliberately rejects safety in favor of experience and growth. Preston-Werner spoke this quote during various interviews and talks throughout his career as a software developer and founder. 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. This perspective gained particular resonance in the early 2010s.
Discussions about meaningful work and the “startup lifestyle” permeated popular culture during this time. 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. It remains 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. The internet was still transforming from novelty to necessity at that time. He discovered programming relatively early and became utterly consumed by it. He spent his teenage years learning code, experimenting with it, building things, and breaking things. He understood 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 programming languages and the underlying philosophy of computational thinking. He learned how to solve problems through iteration. He discovered how to build systems that could scale. This self-directed learning bypassed traditional computer science education at least initially. It instilled in him intellectual independence and a willingness to trust his own judgment over conventional wisdom.
When I’m old and dying, I plan to look back on my life and say, ‘Wow, that was an adventure,’ not, ‘Wow, I sure felt safe.’ What does it really mean
Many people don’t realize that Preston-Werner spent years working relatively conventionally before finding his breakthrough. He worked as a software developer at various companies, including Powerset, a semantic search company that Microsoft eventually acquired. 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 began reshaping the American economy. Most people retreated into conservative positions and sought the safety of established employment. Preston-Werner did the opposite.
He left his job at Powerset to start GitHub. This platform enabled version control and collaborative software development. In doing so, he bet that the world needed a better way for programmers to share code and collaborate. He believed people would find value in what he was building despite the collapsing economy. This decision to launch a startup during the worst economic downturn since the Great Depression embodied his own terms. He chose adventure over safety.
GitHub’s rise proved prescient and transformative. The platform became one of the most important tools in modern software development. Preston-Werner grew GitHub from his garage into a billion-dollar enterprise. Microsoft acquired the company 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 internal conflict and cultural challenges), he continued to pursue new ventures and philosophical explorations. He became an investor and philanthropist focused on scientific research and rationality. He founded organizations like the Human Longevity Project. This pattern of movement perfectly embodies his stated philosophy about adventure. He builds something significant, moves on before becoming comfortable, and starts anew. 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.
Living adventurously leaves a lasting legacy
The quote’s cultural impact has been particularly pronounced within startup and technology communities. It serves as a kind of philosophical north star for the industry’s value system. Entrepreneurship podcasts, startup pitch decks, and motivational social media posts quote it as a rallying cry. However, this popularization sometimes obscures the complexity of what Preston-Werner actually articulated. He wasn’t celebrating recklessness or glorifying unnecessary risk-taking in a toxic way. Rather, he was expressing a belief about life orientation.
A life entirely oriented around avoiding pain, failure, and uncertainty produces a kind of existential anemia. The quote resonates because it touches on something most people intuitively feel. Safety without purpose and comfort without growth leaves something vital unfulfilled. In an era of increasing economic anxiety and unprecedented comfort coexisting with widespread anxiety, Preston-Werner’s declaration feels almost rebellious. It suggests 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. He goes beyond mere startup cheerleading. His philanthropic work, particularly his donations to scientific research exploring aging and human longevity, reveal that his reflection on mortality isn’t abstract philosophizing. Real encounters with the finite nature of existence inform his thinking. These investments in longevity research represent a kind of both-and thinking. Yes, life is finite and should be lived adventurously. Also, extending healthspan and exploring what makes a long life worth living are scientifically crucial endeavors. This nuance suggests that the real adventure isn’t simply embracing risk for its own sake, but rather pursuing a life of genuine meaning and growth while remaining honest about our limitations. The most profound adventures aren’t those that deny mortality, but those that acknowledge it and choose significance anyway.