How I Applied Rule #1
Rule #1 argued that “follow your passion” is bad advice, as the vast majority of people don’t have pre-existing passions waiting to be discovered and matched to a career. The real path to work you love, it noted, is often more complicated. This insight was not one that I encountered for the first time during my quest, but was instead something I had long suspected to be true. Although the chapter on Rule #1 describes my recent efforts to find real evidence for this intuition, the seeds for this thought had been planted long before.
The story of my passion aversion starts in high school, when my friend Michael Simmons and I started a Web design company. We called it Princeton Web Solutions. The origin of our company was modest. It was the late 1990s—the first dot-com boom—and the media was obsessed with stories of teenage CEOs earning millions. Michael and I thought this sounded like fun—certainly a better way to make money than our standard summer jobs. We tried to think up a creative new idea for a high-tech company—something along the lines of a new Amazon.com—but we were stumped and ended up defaulting to an idea that we had earlier vowed we wouldn’t pursue: designing websites. To be clear, we were by no means following our true calling. We were bored, available, and ambitious—a dangerous combination—and starting a company sounded as promising as anything else we could imagine.
Princeton Web Solutions wasn’t a meteoric success, but this was partly by design, as we didn’t really want to invest the time required to grow a serious company. During our senior year of high school we worked with six or seven clients, including a local architecture firm, a local technical college, and an ill-conceived—but oddly well-funded—Web portal targeting the elderly. Most of these contracts paid between $5,000 and $10,000, a healthy chunk of which we passed on to a team of Indian subcontractors, who did most of the actual programming work. When Michael and I left for college—he to NYU and I to Dartmouth—I decided I was done with website design and moved on to more pressing interests, such as girls.
For many in my generation, the rejection of “follow your passion” as career advice is heretical. I never felt this same attraction to the cult of passion, and for this I give credit to my experience with Princeton Web Solutions. As I mentioned, starting this company had nothing to do with me following a passion. Once Michael and I figured out how to keep the business humming, however, this skill turned out to be rare and valuable (especially for people our age). This career capital could then be cashed in for a variety of different exciting experiences. We got to wear suits and make pitches to boardrooms. We made enough money to never have to worry about not being able to afford the types of things teenagers buy. Our teachers were impressed by the company and allowed us to unofficially ditch classes for meetings. Magazines wrote about us, photographers came to take our pictures for newspapers, and the whole experience certainly played a large role in our being admitted to elite colleges.
The traits that can make your life interesting, I learned, had very little to do with intensive soul-searching. Princeton Web Solutions, in other words, had inoculated me against the idea that occupational happiness requires a calling.
Because of these early experiences, I looked on with curiosity, once I arrived at college, when my classmates began to wring their hands about the question of what they wanted to do with their lives. For them, something as basic as choosing a major became weighted with cosmic significance. I thought this was nonsense. To me, the world was filled with opportunities like Princeton Web Solutions waiting to be exploited to make your life more interesting—opportunities that had nothing to do with identifying predestined dispositions.
Driven by this insight, while my classmates contemplated their true calling, I went seeking opportunities to master rare skills that would yield big rewards. I started by hacking my study skills to become as efficient as possible. This took one semester of systematic experiments and subsequently earned me three consecutive years of a 4.0 grade point average, a period during which I never pulled an all-nighter and rarely studied past dinner. I then cashed in this asset by publishing a student-advice guide. These experiences helped me build an exciting student life—I was, I imagine, the only student on Dartmouth’s campus taking regular calls from his literary agent—but neither came from the pursuit of a pre-existing passion. Indeed, the motivation to write my first book was an idle dare leveled by an entrepreneur I admired whom I met one night for drinks: “Don’t just talk about it,” he scolded me when I offhandedly mentioned the book idea. “If you think it would be cool, go do it.” This seemed as good a reason as any for me to proceed.
When it later came time for me to decide what to do after college, I had two offers in hand, one from Microsoft and the other from MIT. This is the type of decision that would paralyze my classmates. I, however, didn’t see any reason to worry. Both paths, I was sure, would yield numerous opportunities that could be leveraged into a remarkable life. I ended up choosing MIT—among other reasons, in order to stay closer to my girlfriend.
The point I’m trying to make in this section is that the core insight of Rule #1 came to me before my quest started, and in fact was something I internalized as early as high school. When I came to the fall of 2011, therefore, and was facing the period of uncertainty when I wasn’t sure if I would become a professor or end up doing something completely different, this Rule #1 mindset saved me from needless fretting about which of these paths forward was my true calling. If tackled correctly, I was absolutely confident that either could yield a career I love. Figuring out how to achieve this goal, however, was less certain, and it was this question that led me to the insights described in Rules #2–4.