Self-Education and Self-Investment

How to Make Your Work Meaningful and Your Meaning Work: Chapter 1 of The Education of Millionaires

I’m going to say something that has probably never been in print before in a business book. It’s probably never been in a business book because, at face value, it sounds kind of depressing.

The bigger the impact you want to make on the world or in your chosen field—the bolder your purpose is—the greater the risks you’re going to have to take. Which means, the greater the chance that you’ll end up making no impact at all. Other than the impact of your ass hitting the floor and failing at your purpose.

In a moment, I’ll elaborate on why this conflict between safety and making a difference, between predictability and living your purpose, exists. I’ll also provide a detailed plan for navigating these rocky waters. But first, consider the following family drama, which plays out in thousands of households across America each year.

Dad and Mom have scrimped and saved for years, maybe even decades, to send their daughter to college, so that she can have a leg up on life. When Daughter gets to college, she decides to major in drama, or art history, or feminist critical theory. A fight ensues:

PARENTS: But how are you going to earn a living from being a drama major? [or art, creative writing, philosophy, literature, poetry, feminist critical theory, underwater basket weaving, etc.] Where are the employment ads that say, “Now hiring full-time drama majors”?

DAUGHTER: But Mom and Dad, this is what I’m passionate about in life. Do you want me to live a life as a faceless office drone, enriching a bunch of corporate fat cats, and let the art inside of me die?

PARENTS: Of course we support your passions in life. We just want you to have a backup plan in case the acting thing doesn’t work out. You’re so smart, you’ve always been such a good arguer. Why don’t you think about becoming a lawyer, like your cousin Sue? Then you can act on the side, on weekends. Acting is a wonderful hobby.

DAUGHTER: You just don’t understand me! Life isn’t just about boring job security! There are bigger things out there, more meaningful things, than how much money is in your bank account. You’ll always regret being the ones who didn’t allow me to go for my dreams [etc, etc.].

Similar arguments play out when high school students tell their parents they’re not planning on going to college, or when college students tell their parents they’re dropping out. In his book You Call the Shots, Cameron Johnson, a wildly successful serial entrepreneur, self-made multimillionaire (and college dropout), recounts two such arguments with his parents.

The first arose during his high school years, when Cameron told them he wasn’t going to go to college, as he was too busy building his already-successful businesses.

“Michael Dell doesn’t have a college degree,” I told them. “Bill Gates doesn’t have a college degree.”

They pointed out that I was not Michael Dell or Bill Gates. I was their son, and they wanted me to get a good education!

Cameron succumbed in that argument and started as a freshman at Virginia Tech. However, soon after starting college, a similar argument arose, when he informed his parents he was leaving college to build his business. He writes in You Call the Shots:

They said, “No, you’re not.”

I said, “Mom, Dad, look at all the basketball stars and football stars who go right from high school to the NBA, or the actors and musicians who don’t bother with college because their careers are already in motion. There have to be business stars, too, who don’t need to go to a four-year program to learn their field. If I go through four years of college, I’ll just be on a level playing field after four years—whereas now I have an advantage. Spending four years in school means I’ll be four years out of the business world. Everything changes like lighting in the Internet world, and they’ll have caught up to me.”

My dad said, “A college education doesn’t hurt anyone.”

I said, “I agree, but it’ll still be there ten years later if I still want it.”

He said, “Cameron, you can lose your house, you can lose your company, you can lose your money, you can lose your wife—but you can’t lose your education. It’s the one thing you’ll always have.”

I said, “That’s true, I don’t disagree, but I am getting an education—a real-world education. Even though I’m not in the classroom every day, I’m still learning, and at a faster pace than my friends in college, because they’re trying to learn about these things in the classroom, whereas I’m learning these things by actually doing them.”

These types of family dramas and arguments, in my opinion, boil down to arguments about our sense of safety versus heroism in life. Safety and heroism are almost always opposed. Imagine a movie in which the hero exposed himself to no risks or dangers, took no chances, and in fact wrapped himself in protective bubble wrap to protect himself from everyday slips and bruises. The movie consists of him walking on the sidewalk, on nice sunny day, in this protective bubble wrap, to go to the store to purchase a few ingredients for dinner. Finito.

Sound like a very exciting movie?

Kids, in their idealism, want to make a big impact on their world. They want to change the world, to feel like their existence makes a difference. They want a big sense of purpose and excitement. They want to be heroes. No kid dreams of being an anonymous paper pusher or a faceless office drone.

Parents want their kids’ lives to feel meaningful and satisfying as well, but they see that the kinds of careers that young people tend to dream about (arts and entertainment, literature, blogging, social media, sports, activism, entrepreneurialism, etc.) are also very risky.

And on that point, the parents are absolutely correct: these endeavors are more risky. In other words, there’s a greater chance you’ll end up flat-out broke if you follow them than if you become, say, a dentist or an accountant.

So naturally, in their inviolable, nonnegotiable role as parents to protect and look out for their children, they tend to advocate safer, less risky, more predictable, more conformist paths as their children contemplate a career. They tend to talk about “backup plans” and “fallbacks,” and to think about their children’s creative passions and quests for meaning as “hobbies.”

Why does this conflict between safety and heroism, impact and predictability exist? For a very simple reason. Almost by definition, “having an impact” or “making a difference” or “living a purpose” involves going beyond what already exists in any given workplace, organization, field, marketplace, or society. It involves innovating, or exercising leadership. Bryan Franklin, whom we met in the Introduction, defines leadership as “creating a future for others which wouldn’t have happened otherwise.” If what you’re trying to achieve would have happened just the same without you, it’s hard to say that you’re having that much of an impact or that your purpose is very significant.

Yet, trying to change the course of the status quo—that is, trying to have an impact, living into a great purpose in your career—is also financially riskier than not doing so. This is just as true if you’re a traditional professional (doctor, lawyer, or manager) trying to achieve big things within your company or your field as it is for people in artistic/entrepreneurial careers, for two simple reasons:

  • People tend to feel safer and more comfortable with the known over the unknown. An “impact” is a change in course, so if you want to make an impact in your field, you’re asking people to venture into the unknown. The more of a change of course your innovation or leadership represents, the more you are asking people to abandon safety and comfort, which is not usually something they’re willing to do without overcoming a great deal of resistance.
  • There may be entrenched interests who are quite happy with the way things are now and who aren’t interested at all in your “impact,” thank you very much. In fact, they may say you can take your impact and shove it! Try to rock the boat too much, make too much of a change, and these people may try to oust you from the organization, community, or marketplace, or even try to harm your reputation or career prospects. Anyone who has dealt with office politics knows this. Any artist or entrepreneur who has tried to do anything innovative knows this.

If you want to become wealthy or famous, which I presume you do if you’re buying and reading a book on success, then you’re going to need to make a difference in the lives of many people. (By definition, it’s impossible to become famous, and it’s also very difficult to become wealthy, if you impact the lives of only a few people.)

Yet, when trying to have an impact on the lives of large numbers of people, two additional challenges arise, unique to the interactions of people in groups:

  • Making an impact on large groups of people involves leading them in some way. Yet, seeking to be a leader is akin to seeking what economists call a “positional good.” A classic example of a positional good is a penthouse apartment. You can’t have a penthouse apartment unless there are apartments below it. Not everyone in society could have a penthouse apartment. Similarly, you can’t have leaders unless there are followers. Not everyone in any given situation can be a leader (unless you live in Lake Wobegon, Garrison Keillor’s fictional town, in which “all the children are above average”). In the real world, not the world where everyone gets a ribbon and a gold star, there will always be competition to lead people. The more people you want to lead, the stiffer the competition. And the stiffer the competition, the less you can be sure you’ll win.
  • Those who do end up leading often achieve leadership, amass wealth, fame, or support, or make an impact on the world, largely through the effects of word of mouth. Followers/customers/fans convert other people to followers/customers/fans, who convert more people to followers/customers/fans, until a big group—which business author Seth Godin calls a “tribe”—has amassed around that given leader, company, or artist. This is how most artists, musicians, actors, writers, and entrepreneurs who become famous and wealthy do so—through the viral-effects word of mouth. When word of mouth takes off, its effects are extremely rapid and dramatic (the “tipping point” that Malcolm Gladwell writes about). Yet, word of mouth is one of the least predictable things on the planet. No one really knows what the next word-of-mouth sensation will be. There’s a capricious nature to word of mouth, fame, and fandom, which has even a bona fide genius like David Gilmour giving a strong nod to the role luck played in his success as an artist.

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 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 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 a hundred 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 what, 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, engineering, 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 “What if?”

Sure, there are a lot of risks of following your passions—the risk that you’ll have to move back into your parents’ basement as an adult, for example, or face near death as a “starving artist.” But, as Randy Komisar points out in his book The Monk and the Riddle, there are also a lot of unacknowledged risks to not following your passions, of sticking too close to the beaten path in the name of safety and predictability. These include:

“[T]he risk of working with people you don’t respect; the risk of working for a company whose values are inconsistent with your own; the risk of compromising what’s important; the risk of doing something that fails to express—or even contradicts—who you are. And then there is the most dangerous risk of all—the risk of spending your life not doing what you want on the bet you can buy yourself the freedom to do it later.”

Randy is a partner at legendary Silicon Valley venture firm Kleiner Perkins Caufield & Byers. A serious meditator and student of Buddhism for many decades (and a fellow graduate of my alma mater, Brown), he’s one of the only people in Silicon Valley who could talk with equal authority on structuring multihundred-million dollar rounds of private equity financing and the finer points of Buddhist philosophy.

I talked with Randy at his office on Sand Hill Road in Silicon Valley. He told me that, a lot of time, people put off taking any steps toward living a more fulfilling life, with the idea of “keeping their options open.” Yet, according to Randy, the idea of “keeping your options open” is an illusion.

Randy pointed out to me that the words “decision” and “decide” stem from the roots “cise” and “cide,” to cut off and to kill, also the roots of many other words related to cutting and killing, such as “incise,” “concise,” (cutting out nonessentials), and “homicide.” Thus, a decision is to cut off, or kill, other possibilities.

“People feel like, unless they’re affirmatively making a decision, they’re not making a decision. They think, ‘How can you fail if you’re not making any decision, not cutting off any possibilities?’ The reality is, you’re making a decision all the time. You’re making a decision not to follow a path that might lead you to fulfillment.

“Even though the choice to do something you don’t love, to ‘keep the options open,’ may seem like a passive decision and therefore less risky, you can’t pretend you’re not making decisions. So the real question is ‘What risks are you taking by those decisions you’re not making?’ Not making a decision to create a fulfilling life now is in fact a decision—it cuts off certain paths in the future. The biggest risk is what we classically refer to as the middle-aged crisis. You become forty-five years old and realize that you’re not the person you wanted to be. You haven’t accomplished what you thought you were going to. The reality is that the vast majority of people today, even when they are on their deathbed, find that their regrets largely center around things they didn’t do, not things they did do.”

Randy calls the safe-and-narrow path, which pretends to incur no risks but which incurs the biggest risk of all (regretting your life at the end of it), “The Deferred Life Plan.” In his book, he gives a simple formula for living this infelicitous Deferred Life Plan: “Step one: Do what you have to do. . . Step two: Do what you want to do. . . . The lucky winners may get to step two only to find themselves aimless, directionless. Either they never knew what they ‘really’ wanted to do or they’ve spent so much time in the first step and invested so much psychic capital that they’re completely lost without it.”

So, according to what I’ve described so far in this chapter, we face a serious dilemma: Either we follow our passions and purpose, and incur a significant risk of ending up as a starving artist, or we follow a safe, predictable, boring path, and incur a significant risk of ending up full of regret in our lives.

Neither option sounds very palatable. Is there a way out of this bind? Is there a way to combine the relative safety and security that our parents advocate with the passion, meaning, creativity, idealism, individualism, and freedom that teenagers and twentysomethings dream about? Is there a way to get the best of both worlds?

Yes, I believe there is.

I’m about to share with you a very specific plan for living the meaningful life of your dreams, making a difference and escaping the rat-race/herd/cage of the predetermined societal/parental script, while also making it less likely that you’ll end up poor than if you followed the aforementioned societal script. I call it the “Art of Earning a Living.”

To explain this art, let me tell you the story of someone who has navigated these dynamics of dreams and dangers with great elegance in the real world. And no, he’s not a gazillionaire, and he’s not famous. But he’s managed to create an amazing life for himself.

Next: Anthony Sandberg and the Art of Earning a Living

Pages: 1 2 3 4 5 6 7

Previous Post Next Post

You Might Also Like