The Education of Millionaires - Michael Ellsberg [18]
In your career, whenever you are faced with two paths, you will almost always be facing a choice between one path that is more predictable (in which you’re more or less a cog in a predetermined script) and one that offers the chance to make a bigger impact (e.g., a leadership position) but has more risks associated with it. This is as true for a lawyer or corporate manager as it is for a start-up entrepreneur or a musician.
Another way to see it: at any point in your career, you’ll usually be choosing between one path that is safer and one path that has the potential to feel more meaningful to you, between one path that is more certain and one that offers more of a chance for a sense of purpose and heroism. It’s hard to be a hero if there’s no risk involved.
A good way to think about “living a meaningful life,” to a first approximation, is “making a difference in the lives of people you care about.” It’s no wonder our sense of meaning is so tied up with myths and stories—the heroes of myths and stories take risks in order to make a difference in people’s lives. If you’re not making a difference in anyone’s life, it’s unlikely you’ll feel that your own life has been meaningful. You may end up, like the title character in “The Secret Life of Walter Mitty,” living a mediocre life and merely daydreaming of heroism.
This is, as Thoreau put it, a “li[fe] of quiet desperation.” Truly making a difference and living into a meaningful purpose has all kinds of dangers associated with it, including the dangers of failure, rejection, even ruin and going broke.
So, how do we navigate our desire for safety with our desire to make a difference in the world? How do we navigate between our desire for heroism, adventure, and romance and our desire for some level of predictability in our lives? How do we reconcile our idealistic dreams with the harsh realities of the marketplace?
These are the questions I answer in the rest of this chapter, indeed in the rest of this entire book. One thing I’m not going to give you, I promise, is a bunch of unrealistic fluff, yet another cheery pep talk about “never giving up on your dreams.” Whenever I hear that kind of motivational guru-speak, I think of someone standing next to me as I contemplate a bet on a roulette wheel, telling me: “Think big! Never give up on your dream that putting your entire life savings on the number six could pay off big. And if you lose, double down—borrow if you have to—and keep going! Don’t give up! You’ll hit it big one of these days!”
The chance of becoming a true star in any given field, on the level of a David Gilmour, or some of the other self-educated mega-famous or mega-rich people I feature in this book (such as billionaires John Paul DeJoria, Phillip Ruffin, and Dustin Moskovitz), is orders of magnitude tinier than the chance of picking the winning number on a roulette spin. It’s more like picking the winning number several spins in a row.
I don’t advocate gambling. So I’m not going to tell you to quit college, or quit your comfy corporate job, to pursue your acting career or your singing career or your writing career.
So, am I telling you to give up your dreams, stick with the societal program, get that boring, safe job, and do just as your parents told you? No. The problem is, there are serious (though much less frequently acknowledged) risks to that path as well. If you’re not particularly passionate about accounting, corporate management, law, or engineering (the traditional professions), and you go into those fields to please your parents, or to placate your own fears about the risks of following your creative passions, it seems very unlikely to me that you’ll end up happy with your career choice. You will always be plagued by a nagging sense of