← the shelf
Sadly, he was right; for a variety of reasons that seem impossible to understand today, my father’s family was not accepting of the budding courtship. The fight grew so contentious that he was ultimately forced to choose between his family and my mother. I never met my father’s parents, and he never saw them again, but the legacy of his decision—to choose true love above all else—set the stage for the world that I was born into. My childhood and young-adult years were a steady, monotonous march toward a textbook definition of success. I did well in school—maybe not according to my discerning Indian mother, who continues to this day to ask, “Why not try for medical school?”—but my thoughts were always on the baseball field. With some natural ability and a hell of a lot of hard work, I earned a scholarship to pitch at Stanford University.
To try to solve that puzzle, I did what I thought any ambitious young person would do—I went to the richest people I knew and asked them about their work and how I could get into it. I vividly recall a formative conversation with a family friend who had made a fortune in the world of investing. He suggested I join an investment firm straight out of school, and his case was simple: “You’ll make a hundred thousand dollars a year right away, five hundred thousand a year soon after that, and by the time you’re thirty, you’ll be making more money than you know what to do with.” That sounded pretty damn good to me on the basis of one simple, foundational assumption: Money will lead directly to success and happiness.
Mark Twain is often quoted as having said, “It ain’t what you don’t know that gets you into trouble, it’s what you know for sure that just ain’t so.” Well, when I took the advice of my family friend and accepted a job in California where I would earn well into the six figures in my first year, I knew for sure that this was the beginning of my road to the good life—that if I put in my time, I’d eventually reach that stress-free future filled with money and happiness. What I knew for sure just wasn’t so; I simply hadn’t realized it yet.
How many times has the thing your younger self dreamed of become the thing you complain about once you’ve gotten it?
Worse yet, the incessant quest for more had blinded me to the great beauty of what I had right in front of me. In a fable recorded in Plato’s early works, a philosopher named Thales of Miletus is walking along obsessively gazing at the stars, only to fall into a well that he did not see at his feet. A poetic retelling by Jean de La Fontaine concludes, How many folks, in country and in town, Neglect their principal affair; And let, for want of due repair, A real house fall down, To build a castle in the air?[1]
The greatest discoveries in life come not from finding the right answers but from asking the right questions.
In each conversation, I walked through a beautiful visualization exercise that had been recommended to me by a mentor. Close your eyes and imagine your ideal day at eighty years old (or one hundred, in the case of the ninety-year-old!). Vividly imagine it. What are you doing? Who are you with? Where are you? How do you feel? The exercise forces you to begin with the ideal future end in mind—it establishes a personal definition of a successful life that can be used to reverse-engineer the actions in the present to achieve that desired end.
We all want the same thing—and it has very little to do with money. From the young entrepreneur to the old retiree, from the new mother to the empty nester, from the rich attorney to the middle-class teacher, the ideal future end looks remarkably aligned: Time, people, purpose, health.
