Drop Out of The System, Drop Into Success – The Dartmouth Lecture

[Below is an edited transcript. There is also an audio version available for streaming and download at the bottom.]

I’m going to open with a statement that I guarantee that every one of you in the audience is going to find shocking.

I think every one of you students in the room here should consider dropping out tomorrow.

Obviously I don’t mean that in the literal sense. If I did the people here at Dartmouth who brought me in to speak would get fired tomorrow, and I don’t want that. So what the heck do I mean?

I’ve spent the day here on this lovely campus, and one of the messages I’ve heard from various people—both students and faculty—is that there’s a kind of track going on here. It’s not unique to Dartmouth, but maybe it’s more pronounced here. That is a track of doing well in school, then coming here and doing well at Dartmouth, then going on to a “respectable” profession. The professions I’ve heard are really popular here are management consulting, investment banking, and law. So the picture I’ve gotten is of a place where young people are brought on a track from a young age and then are put into a “tracked” career.

I’m not trying to single out Dartmouth here. I went to Brown, where it’s pretty much the same thing. We have a slightly different relationship to conventionality there, but most of the people are still being groomed for, and going into, these kind of “traditional” careers.

When I say you should consider dropping out, I don’t mean that you should consider dropping out of this institution. Please don’t do that! However, I do think you should consider dropping out of that “track” I mentioned. What I hope to accomplish by the end of this talk is to instill in some of you a broader perspective on the range of careers that are possible for you after you leave this institution—which will still allow you to lead a happy, comfortable, and successful life.

Before I go any further I just want to point out that I don’t have anything in particular against management consultants or lawyers or investment bankers. I’m using an Apple computer that probably required a lot of investment to make. I’m wearing a suit that was made by a company that probably required lawyers and consultants. Society needs people that pursue these professions.

We need doctors, and we need lawyers. So if you are one of those people who always wanted to be a doctor, or a lawyer, and you’ve dreamed about that since you were a kid… If you are one of those people who always wanted to be a deal-maker out on Wall Street, wining and dining clients and making deals… Then by all means, follow your dreams.

However, I speak to a lot of young people, and what I find is that a majority of them are considering those professions, but a very small minority of them seem to have any idealism about it whatsoever. I don’t meet that many people who have a really idealistic concept of why they want to go into law, or why they want to be a doctor, or an investment banker.

Instead, I meet a lot of people who seem to be going through the motions. They just think that’s kind of the thing to do. Especially if you come from a fairly privileged background, and have access to institutions like Brown or Dartmouth. Investing a lot of money into your education in order to pursue these kinds of career is just the thing you do if you want to live a materially-comfortable life.

My goal is to broaden your perspective and suggest that there are actually other paths you can take that will still allow you to live the life you want to live. Paths that don’t involve dropping out of the institution, but do involve dropping out of that narrow career track.

I think I’m a good person to speak about this, because I spent two years interviewing people who literally dropped out of college, and then went on to find their own path and became successful entrepreneurs. I interviewed about 50 self-made millionaires and about five self-made billionaires.

I believe each and every one of you has the potential to have a massive impact on the world through a path that you create. Not a path that was created for you.

I want to make a distinction between two kinds of extremes I tend to see people – especially young people – navigate towards when they’re figuring out how they want to relate with the world of work. The two extremes might be caricatured as the “Suits” and the “Hippies.” This is actually a distinction that one of my mentors, Bryan Franklin, came up with. He is someone that integrates these two worlds really well.

Let’s start by talking about the Suits. By the way, if you had to guess which of the two extremes someone at an elite educational institute tends toward, it’s probably the Suit. The stereotype of the Suit is someone who plays it safe and narrow. This is someone that mostly follows the rules their parents and society set forth for them. He or she doesn’t really rock the boat too much, but rather learns how to navigate within the institutions around them and make their way through the halls of power.

The Suits get rewarded pretty well for that. All of you could absolutely have that life. My guess is that you’re already on that track. You’re in one of the most elite educational institutions in the world. Provided you don’t party too much, and you maintain a decent grade average, you’re going to graduate with a diploma from here. Which makes that lifestyle absolutely open to you. And there’s nothing wrong with that, if it’s what you want to do. The Suit lifestyle offers a certain amount of economic stability, which is probably why most of your parents pushed you to get into an institution like Dartmouth. I’m guessing your parents would be delighted if you become an investment banker, or a lawyer, or a doctor. Because there’s a certain amount of predictability to the income you’re going to have with that path.

The problem with people who take that path without thinking about it or questioning it, is what could be colloquially referred to as the “mid-life crisis.”

Let’s play this scenario out for a moment. You went through your entire high school experience working to get into Dartmouth. Once you’re at Dartmouth, you work hard to get a good GPA and an impressive resume. The investment banks come here to recruit and you get a summer internship or two. Then, after graduation, you get a full-time job as an investment banker. You work 100 hours of week, get paid really well and party with your investment banker friends on the weekends. Maybe you start with a salary of $75K or $100K a year, then in a couple of years it’s $200K. If you really work the system you might get up to $500K or even $1 million. Everything is going great.

Except some (not insignificant) portion of the people who take this track “wake up” at some point in their life—usually somewhere around mid-life, in their forties or fifties. They wake up and realize they’ve been asleep. All of a sudden they’re half-way through their life and they haven’t really made any of their own choices about who they are and what they want to be in this world. They’ve just followed what was set out for them by their parents, and by the social circles they were in.

That’s when you get all kinds of weird behavior from people. People get divorced—which isn’t weird in and of itself, but it does go along with some of the other changes you’ll see around this time. They go to psychotherapy, they become a life coach . . . They do something to get out of that system. Usually that involves moving in some sense towards the other pole, which I’ve caricatured as the “Hippie.”

In my twenties, I gravitated much more toward the Hippie. Before that, I went through the system. I went to Deerfield Academy for high school, and did very well academically there. I went to Brown and did well there. I graduated from Brown, class of 1999, and spent most of my twenties totally lost. I was trying to integrate the kind of “tracked” system I had been put through in my teens and early twenties, with what felt meaningful to me.

I was very lucky, or very unlucky, depending on how you look at it. I had my mid-life crisis early—through my entire twenties. I was very lost. I knew that I was passionate about writing. I knew that I was passionate about social questions, and the environment, and literature and philosophy, and all these things that lit my brain and my soul on fire. I just didn’t know how to integrate those with actually receiving a check.

Part of my twenties involved moving back with my parents. Which is not such an uncommon phenomenon now. I read a statistic that 85% of recent college graduates are moving back with their parents. Our society clearly has some problem with how to raise young people into independent adults, who can exist outside the orbit of their parental support systems, if 85% of young people—including me—are going right back to that support system as soon as we get out. There’s something wrong there.

As I was trying to figure this stuff out, I went more and more in the Hippie direction. The way I define the Hippie is that it’s focused on meaning, or the question of, “What’s going to be meaningful in my life?” without much attention to, “How am I going to pay the bills?”

The way this manifested in my life is that I was very passionate about writing. So I spent several years writing what I hoped would be this groundbreaking literary work of fragmentary, manic, non-fiction. Turns out there wasn’t a big market for it. I got rejected 22 times by the New York publishing industry.

I was a bitter, angry, wannabe artist, the starving artist. Fortunately, I wasn’t literally starving. And the only reason I wasn’t literally starving is that I had very generous parents, with a very generous basement. So that’s what happens when you go too far to the Hippie extreme. You say, “I’m going to do what’s meaningful to me, and I’m not going to pay attention to how that interfaces with society at large, with markets, money, and existing institutions and spheres of power.”

What I encourage now—what I spent the latter half of my twenties and my early thirties trying to figure out—is some integration between those two extremes. An integration that allows us to express what is meaningful to us, so that we’re not at risk for waking up one day when we’re 45 and thinking, “What am I doing with my life? What does this all mean?” Yet, that also allows us to live a materially-comfortable lifestyle. Not necessarily an extremely wealthy lifestyle, but definitely a lifestyle where we’re not worried about money that much. Where money is handled so you can put your focus on other things, like how to express yourself, and how to contribute to your community, or to society at large.

Achieving this integration has been the focus of my life for the past 7 or 8 years. Specifically it’s been a major focus over the past several years as I was writing and talking about The Education of Millionaires. The people I interviewed for my book all have one thing in common—besides being dropouts—which is that they’re entrepreneurs.

I think entrepreneurship is that path in society that offers the best shot at what I’m talking about—the best shot at integrating the Hippie and the Suit, the best shot at integrating what you care about and what you’re passionate about with what will actually allow you to live a comfortable lifestyle.

We have a jobs crisis in America right now. Unemployment is at record highs. I just read a New York Times article titled, “Many with New College Degree Find the Job Market Humbling.” It cites a statistic that, of college graduates under the age of 25 right now, 22% of them don’t have jobs. The Great Depression was 20% unemployment overall. So right now we’re actually in a Great Depression for college-educated young people.

Another article I read from one of our nation’s most reputable news sources, The Onion, says, “New College Graduates to be Cryogenically Frozen until Job Market Improves.” You all are graduating to a very different climate than when I graduated in 1999. Those were the go-go days. You could have the most harebrained idea, and someone wanted to give you $10 million to execute it. You could just show up on the doorsteps of Silicon Valley with a college degree, and be hired by some dot-com that was funded by tons and tons of venture money and wanted to spend that money as fast as possible on the growth of the company.

That was the environment I graduated in. Of course that all “popped” in 2000-2001. Then things improved again in the mid-2000’s. And now we’re in a harsh place for young people. It’s not pretty what’s facing all of you out there. Because you’re at Dartmouth, those of you in this room probably have a better shot than the average young people in America. If you try hard you’ll most likely avoid that cryogenic freezing and having to move back in with your parents. But it’s still tooth-and-nail right now. You’re probably feeling some of that competition in the limited companies that are recruiting for jobs here.

What I want to suggest is that some percentage of you should consider dropping out of this “track.” Stop fighting with each other for the few pre-existing jobs the management consultants want to give you. Become, not seekers of jobs, but creators of jobs. That may sound very grandiose, but it’s really not. In fact, I’m a job creator myself. I’m self-employed. I don’t have any employees. So what makes me a job creator? I created one job—for myself.

I honestly believe that all of you in this room could create a job for yourself, straight out of college. That path is open to you. It’s especially open to you given that you’re bright, motivated, and have connections—which I know is the case since you’re here at Dartmouth. You have connections with each other!

I was having a really interesting conversation with Andrew—the Director of the center here—just before I spoke, and he said something that I loved. He said, “The entrepreneurship recruiters don’t come to campus.” What does he mean by that? There are a lot of startups out there looking for talent. There are a lot of dynamic, interesting, small companies that are dying for the kind of talent that you guys have in this room. There’s actually a talent shortage in the entrepreneurship world.

This surprises a lot of people because there’s all this talk about the lack of jobs and the cryogenic freezing of the job market. However, in certain segments of the economy—most notably among entrepreneurs and startups—there is in fact a shortage of talent. But here’s the secret: those people and companies are not interested in hiring you if they have to come find you.

Management consultants have a whole track. They’ve been doing this for decades. They take raw talent and give them $75K or $100K a year to live and work in New York City. Then, over several years, they hone that talent into management consultants. They can take pretty much anyone who has a pulse, and is reasonably intelligent, and turn them into a management consultant.

I’m not trying to dis management consultants. You have to be just as smart to get to the elite levels of that profession as you do to succeed l in any of the other careers I’m talking about. What’s different about management consultants vs. entrepreneurs is that the former basically selects for people who are reasonably good at following orders. When you go through the educational system in America—especially at the more elite levels—you’re basically being selected for and trained to follow orders. I was the product of this system, so I really don’t mean any offense by this. It’s just an observation.

This doesn’t happen on the micro-level. I’m not saying that your teachers and professors are trying to tell you exactly what to think. Of course not. In fact, I had lunch with several of your professors here at Dartmouth and they said that they wish you would think outside of the box more. Your professors are dying for your creativity.

But there is a general sort of falling in line that happens through the educational system. Just think about the act of sitting in class. You take a 6-year-old boy who wants to go throw things and punch things and run around. He has all this creative energy—and he’s told to sit still in class all day, every day. He’s trained to follow orders. This becomes more subtle over time. In high school you’re told to do well on the SATs. You take part in narrowly-defined extracurriculars like Glee Club, or the Student Newspaper. Then in college there’s yet another version. What doesn’t change is that you’re being trained to fit into a bureaucratic system, where there are hierarchies of authority. First it’s teacher-student. Then later, in the workplace, it’s boss-employee. There are these levels of authority and you’re trained to get gold stars, or A’s, or 98%, depending on how well you interpret what your authority figure wants, and deliver that to them.

That works for a certain segment of the economy. Again, I’m very happy that there are a lot of middle managers at Apple who helped produce the laptop that I use. But who created Apple? Apple was created by a guy who dropped out of Reed College. After dropping out, he continued to hang around campus and took classes illegally without paying for them. Calligraphy classes, not business classes. Then, he decided he wanted to go explore India and search for a guru—a decision that we now know from his biography, came after he dropped large amounts of LSD. From there he continued to create his own path, part of which involved founding Apple.

I’m not recommending anyone drop out of Dartmouth. Nor am I recommending you take LSD, or go search for your guru in India. I am sort of recommending that on a metaphorical level, however. I’m recommending that some percentage of you opt to not become the middle-of-the-road programmer, or the middle manager, who does the paper shuffling and grunt work it takes to get something like an Apple computer produced.

The people who create those innovations—Steve Jobs with Apple, Mark Zuckerberg and Sean Parker with Facebook, Bill Gates with Microsoft—the people who own the businesses and create the jobs tend to be either literal dropouts (which is a minority) or metaphorical dropouts. By a metaphorical dropouts, I mean that at some point they opted out of the system.

You don’t see a lot of MBAs as CEOs. The MBAs tend to get hired by the CEOs. To get to the CEO-level of leadership, usually you forge your own path. You don’t just go through the systems that are already in place. By definition, a leader cannot be someone who just follows orders. The leader doesn’t necessarily have to be the one giving orders. But he or she is usually the one creating the culture or the direction for where the organization or business is going. Leadership is not following someone else’s path. It’s about clearing your own. And that requires a very different skill set.

How can you do that here at Dartmouth, and after you graduate? I’m going to say something now that may piss off some adults. But that’s okay, because I’m here to talk to the young people in the audience. Most of the economic benefit that you will derive from having gone to Dartmouth has already been achieved by the fact that you got in. As long as you don’t party too much and keep your grades within a reasonable range, you’re going to get a diploma. And having a diploma from Dartmouth—regardless of your grades—is the majority of the economic benefit you’ll get from your time here.

It’s like your societal stamp-of-approval that says, “This is a smart kid who knows how to follow orders, plays well with others, and knows how to fit in. This is someone we can hire and put into our bureaucratic system.”

So, given that you either have that stamp-of-approval, or are on your way to obtaining it, how should you spend the rest of your time here? There are a lot of other benefits you can get while you’re here at Dartmouth that have nothing to do with that system.

What am I talking about? Basically, anything that will allow you to practice leadership. Anything that gives you a chance to think on your feet, work with other people, create things, pitch things, communicate persuasively, resolve conflicts, or reach out to other groups that may lend you support.

The nuts-and-bolts of leadership is a non-academic discipline. You cannot learn to be a leader in a class. You just can’t. You can learn some interesting things about leadership in a class,or from reading books. I have certainly learned about leadership from reading books. But that’s only 10% or 20%. Eighty percent of learning in leadership comes from actually being a leader on the front lines.

There are two exceptions to what I’m saying here. First, if you are passionate about becoming a professor, or a research scientist, then this advice I’m giving you is bad advice. If academia is your path, then you really need to focus on academics. Absolutely.

Second, if you’ve heard everything I’ve said about Suits and Hippies, and you still want to continue on your “track” to becoming an investment banker (for example). If you’re set on your path, and I haven’t persuaded you here to metaphorically drop out of that “track,” then absolutely try to get as high of a GPA as possible.

If neither of those exceptions apply to you, then I would suggest that your best educational opportunities now are actually not going to come through buckling down and getting the best-possible GPA. I’m not saying cut class. Rather, you might consider taking a class that’s off the beaten path. Steve Jobs talks openly about how influential that random calligraphy class at Reed was for him. Take your version of that calligraphy class—on a topic that has no practical purpose whatsoever, is not monetizable, and doesn’t fit in well with what you think an investment banking recruiter would be looking for.

Outside of classes, I think the emphasis should be on learning to work with your amazing peers. You have some of the most interesting, bright, motivated young people on the planet here as your peers. The more you learn to work with them, the more success you’re going to have.

Teamwork is a cliché, but it’s also critical to your success, and it take a lot of practice to learn how to do it right. You have to learn about communication. You have to learn about persuasion. You have to learn about compromise. You have to learn about collaboration. These are disciplines, just like sociology and economics are disciplines. But they’re not academic disciplines—they’re practical, street-smart disciplines.

How do you communicate with other people? How do you persuade other people to your viewpoint? How do you listen to other people’s viewpoint, and have empathy, and understand where they’re coming from? How do you inspire other people? How do you motivate other people? How do you manage conflict? How subtle and sophisticated is your level of understanding of the power dynamics within a group of people? Do you know how to navigate those power dynamics? How do you work a room? All of these skills relate to leadership. The stuff of leadership is the stuff of practical intelligence.

You already have enough academic smarts. You’re good in that department. What I hope to inspire you to think about, are questions like: “How can I go out and create opportunity for myself, and other people?” “How can I go out and interface my passions, my dreams, my desires, with the power sources and the structures of money out there?” “How can I be a job creator?” “How can I create one job – a job for myself?”

I’m suggesting that you can actually bypass this collective freak out that young people are having right now about where and how they are going to get a job. Whenever constriction happens in a system, people fight harder to “win” within the limited metrics of that system. Right now there is constriction in the “track” or “path” I’ve been talking about. There are fewer corporate jobs. There are fewer management consulting jobs. There are fewer investment banking jobs. So the people who still want to bust through those gates are working harder at the very same things. They’re taking more finance classes and staying up nights to try and get one or two percentage points higher on their tests, or their GPA. It has the feeling of a herd stampeding through a bottleneck. There is this frenzy to get through, but only a small percentage make it. Everyone else is getting trampled and burned out along the way.

You can opt out of that system. In the entrepreneurial world it’s a completely different game. There is so much opportunity right now for people who learn these practical skills. There is a dearth of young people who are able to create opportunity for themselves. There is a lack of young people who are good at those things because our entire educational system views those skills as less important. Instead, it trains people to become more and more efficient at getting through the doors of that limited track system that I’ve been talking about.

Here is a website all of you should check out. It’s called, “Working for Wonka: Surviving a Startup.” This is the first website of its kind that I’ve heard of. The basic idea of the site is telling you how to go about getting a job in a startup. I’m not talking about going to Silicon Valley and getting a job at Facebook or Google or Apple. Those companies are no longer startups. Working for them has more in common with the management consulting track than with the entrepreneurial track at this point.

That site is about how to get a job at the next Facebook, or the next Google—when it still has less than 20 employees. It’s a totally different mindset (and skill set) than the one you’ve been groomed for by your parents. This is a mindset where leadership and initiative are prized. You’re rewarded for NOT following orders. In a startup environment, simply following orders is a liability. They need people who can wear many hats, think in innovative ways, generate ideas, and act on those ideas without a lot of guidance and structure.

My suggestion to you is to opt out of the freak-out everyone is having about how many jobs there are on Wall Street, and who can get the limited number of management consulting positions. There are greener pastures out there, companies that not only want, but are begging you to learn this other skill set that centers around leadership. My hope is that some of you take this message and focus the rest of your time here on becoming outstanding, excellent leaders. When you do this, you’re going to find that there’s a world of economic opportunity available to you.


Q: This is more of wanting reassurance than a question. Personally, I don’t ever want to know my IQ. I just don’t really want to limit or define myself in that way. But for the standard level of academic achievement you said is necessary to not have to focus on that anymore—could we safely assume that if we got in to Dartmouth, we’re at least at that IQ?

M.E.: Absolutely. IQ is an extremely controversial topic in America. I don’t want to get too deep into that debate, but one point that I want to make is that IQ is very correlated with what I would call “academic intelligence.” The same kind of intelligence that allows you to do well on an IQ test is highly correlated with the kind of intelligence that allows you to do well on academic tests and writing academic papers. It’s a kind of analytical intelligence where you’re breaking large concepts down and analyzing them. I don’t want to put numbers on it, but you can absolutely assume that if you got into Dartmouth, you’re cool in that department.

The other kind of intelligence has a lot of different names. Let’s call it synthetic intelligence. IQ is about analysis, and breaking things down. Synthesis is about taking pieces and re-arranging them in new and interesting ways. How can you take a bunch of different pieces—before Apple computers existed—and create an Apple computer out of them? That requires a totally different use of your brain than IQ. If you want to do something outside of the “tracks” that I’ve been talking about, then you’ll be better off developing the synthesis type of thinking instead of the analytical type of thinking.

Q: I know that you’re not recommending dropping out of college, but for the students who are working on a startup, following their vision, and have funding, how do you reconcile studying part-time and also working on a startup part-time?

M.E.: I’ve been saying, “Don’t drop out,” and I think that is true for 99.9% of the students here. If you went through the trouble of getting in to a place like Dartmouth, you might as well get your degree. I am also saying that because I don’t want the people who brought me here to get fired! However, there is a very small minority of students who I think actually would be better off focusing on a startup. If your startup isn’t just some pie-in-the-sky, harebrained idea that you dreamed up in a late-night bull session—and you’ve actually gotten traction/revenue/users for your idea—then it may be a valid decision to temporarily see if that is going to be the source of your education. A startup can be a wonderful source of education. But you have to go full-in. To launch a real startup, you can’t really do it in a half-assed way. It’s an all-or-nothing commitment.

I interviewed Dustin Moskovitz, one of the co-founders of Facebook, for my book. His is a legendary story now. He and his cohort at Harvard started Facebook, and when it got massive traction within a few months, they spent the summer out in Silicon Valley working on it. By the end of summer it was clear to them that they were getting way more of an education doing that, than they would back in school. By that point they knew it was a valid idea. Dustin made an interesting point in our interview though. He said, “I didn’t drop out right away. I just decided to take some time off to pursue this idea.” Most educational institutions have some tolerance for their students taking a semester or a year off to pursue an opportunity. And I think for a minority of students, that is an appropriate decision.

Q: Going back to your story, and also correlating to Bill Gates, you guys didn’t have an idea right out of college and suddenly run with it. It took a lot of struggle—you said you had your artist crisis. Malcolm Gladwell also said that it takes 10,000 hours of experience before we get good at something. So how do we go on a track to get that experience without being on “the track”?

M.E.: Great question. The best solution to have some space in your life to explore creativity and passions, while also being able to pay the bills, is to get a day-job. Getting a day-job while you pursue your creative passions on the side is a tried-and-true solution that people have been using for decades, if not centuries.

For example, I’m a writer. It’s very difficult to get paid well as a writer, right from the start. And it’s getting even more difficult—almost impossible—with the proliferation of free content. I happen to make my living now as a writer. I’m not going to get super wealthy from it, but I support myself, in New York City, as a writer. I’m 35 now. That didn’t happen when I was a want-to-be writer at 25. I had to do other things that weren’t writing to pay the bills. Or rather, I did a form of writing, copywriting, that was less creative, and more likely to earn me money.

My general talent area has always been around words, and persuasion with words. That is a talent that can actually be monetized fairly well, if you’re willing to help other people market their businesses through words. Examples of this are copywriting, or writing proposals. So for a long time, I had my day-job form of writing, which was writing proposals. It wasn’t like I woke up and had this strong desire to write proposals every day. But because they were paying me, I would do it. That gave me the space and time—without a boss breathing down my neck—to pursue the writing I was passionate about. Over time that evolved to where I started getting paid more and more for that, and now I’m making a liveable income from writing about topics I feel passionate about.

There’s a lot of historical precedents for the day-job model. T.S. Elliot worked at a bank for many years. Kafka was an insurance agent. The starving artist model is just one model. There are people who have been exploring other ways to support creativity for many years.

Q: What if what you actually want to do isn’t able to provide a sustainable lifestyle? What if they don’t match up? How do you get to the point where you commit fully? Like if you’re going to pull a “Zuckerberg.” It could be Facebook or you could end up broke and working at McDonald’s or something. Nothing wrong with that, but how do you get to the point with risk-taking where you can make a valid assessment on the likely success rate? I’m an actor and musician, and that’s one of the tricky ones where you could end up severely successful, or working as a waiter. You never know what you’re going to get.

ME: You pointed to something really important: the more creative a discipline is, the more variance there is in people who are successful at that discipline. Let’s consider a fairly uncreative discipline, relatively speaking: accounting. There’s not that much variance as to the success of accountants. There are some that do a bit better, and some that do a bit worse. But pretty much everyone who satisfies the minimum requirements to become an accountant does okay.

More creative endeavors – like acting, music, writing, and entrepreneurship – are exactly the opposite. They have a different model, where a very small percentage of people who pursue that as a career end up wildly successful. In acting, it’s all of the actors you’ve heard of, like Tom Cruise and Brad Pitt and Angelina Jolie. For every one of them, there are a million other people who are “actors,” who serve you your fries at McDonald’s. The same is true of music, and writing.

Let’s just say you want to make it in a field like acting, where there’s a really uneven skew of who is successful and who is not. I’ve been talking overall in society about this systematic, “tracked” path versus the more out-of-the-box entrepreneurial way of thinking. That actually is true within each field as well, including the more creative fields like acting. There’s kind of a way that you’re supposed to be an actor, right? Technically there’s sort of a “New York way” and an “LA way.” We’ll talk about the New York way, because that’s closer to here.

You graduate from a liberal arts college, like Dartmouth or Brown, and move to New York, to some shit room in a shit apartment way out in Brooklyn for $500 a month. You live with cockroaches and rats. You get a bartending job. And the rest of the time you go to auditions. In other words, you beg and supplicate people to give you opportunity—just as some of your peers are supplicating for the management consulting recruiters to give them opportunity.

The basic assumption of all of this is that opportunity is given to you, and you beg for it. This exists in each field. Well, just as I’m encouraging you all to take a more entrepreneurial approach to your careers, if you specifically want a more risky career—like acting, music, writing—I would suggest you take an entrepreneurial attitude to that too. Think, “Okay I’m passionate about acting. How can I create some opportunity around me that involves acting, gets me paid reasonably well, connects me to the right people in the acting world, and gives me some flexibility and freedom to pursue my more avant-garde tendencies (which I probably won’t get paid for otherwise)?”

There are all kinds of things you could do. I just met a woman who is an actor and a stand-up comic. It’s extremely difficult to make a living as a stand-up comic through the “track” of stand-up comedy. The track is: you travel around the country, going to a bunch of free open mics and hoping that someone gives you opportunity. And maybe one thousandth of one percent of the people who go through that system actually make their living from it.

This woman was passionate about comedy, knew she wanted to devote her life to it, and didn’t want to take that roll of the dice, which looked very unfavorable. So she started teaching stand-up to CEOs. She said, “Look, you guys have to be on your feet all day long. You need to learn how to think on your feet. You are leaders, and you need to have some comic relief in your leadership, so it’s not so stuffy and dry.” This woman is making a lot of money teaching improvisational comedy to CEOs and managers in the corporate world. She gets paid a lot, she doesn’t have a boss, and she gets to pursue her more artistically “pure” endeavors as well.

Q: You’ve linked entrepreneurship and leadership with practical intelligence. I’d like to ask you where ruthlessness comes into it. I’ve started the fourth volume of Caro’s biography of Lyndon Johnson, and recently I’ve read a couple of scathing reviews of Steve Job’s personality. You have this guy in England who is head of Barkley’s and he’s calling people in the House of Commons Committee by their first name. You have examples like John Edwards and John Kennedy. These people are ruthless—they’re not nice people. How much of that comes into pla


I don’t want to assume anything about you because I don’t know you, but in general that question is a way that the people on the “Hippie” side of things think about people on the “Suit” side of things. Again, I’m not saying anything about you. But I’ve heard that kind of concern voice from people like me who took the starving artist route: “Well, it would be nice to have more money, but I have to be an asshole to have more money. And I don’t want to be an asshole so I’ll just be broke.”

I think that’s an incorrect way of thinking. Look at leadership around the world and there’s a spectrum. On one end of the spectrum is Attila the Hun. On the other end of the spectrum you have the Dalai Lama, Gandhi, Martin Luther King, Mother Theresa. One thing that’s really important to keep in mind is that none of these leaders are actually saints. We tend to project a lot of saintliness on to them, and then we get really disappointed when they don’t act like saints—that is, when they act like humans.

For example, it’s widely known that Martin Luther King cheated on his wife, and had mistresses. Gandhi was up to some weird things. He was celibate with his wife, but then he slept with nude teenaged girls in his bed to practice his ability to not avail of himself to his desire, or something like that. There was just some weird stuff going on with the guy. He wasn’t a saint—he was a human being. Yet, I would say on the spectrum of leadership, he embodies the best kind of leadership that’s possible for humans. It’s a leadership that takes opposing sides and seeks to find a better synthesis for them. That’s what all of those leaders did. They didn’t have this ruthless, kill-your-enemy mentality. Instead, they were leaders by saying, “We’re going to overwhelm our opponents with such extreme power of our soul, and our love, that we will not only bring them over to our side, but we will also learn something from them that will help us find a better, more inclusive synthesis.” That’s an ideal, but it’s a great ideal. And I think certain leaders have successfully embodied that ideal.

Q: I just want to make a pitch for the liberal arts here, because I think in a startup particularly, or in smaller businesses, a leader has to do pretty much everything. You get to be a lawyer for half an hour a day. You have to write. You have to manage personnel. You have to have taste in looking at your advertising. You have to deal with people. It’s a whole broad range of responsibilities. If you come to a school like this and you take 14 courses in economics, and the rest in math, you’re missing out on a whole broad range of experiences that you can get here, which will help you in the future.

M.E.: Absolutely. I’ve talked about two ways you can avoid “the track” that’s going to get you into a 100 hour a week consulting job. By the way, just a minor warning about that track that I’ve seen, and have never heard said elsewhere: part of what is enticing you to go on that track is the money, right? You probably wouldn’t be doing all this stuff if they were paying $30K a year. What are the starting salaries these days for management consulting? Is it $75K or $100K, something like that? That’s good money.

But here’s the thing. Let’s say you get a management consulting job with a starting salary of $100K a year. It’s actually not one full-time job for $100K. It’s actually two 40- or 50-hour a week jobs for $50K each. If someone were to offer you one job for $50K you’d say, “I don’t want that, it’s only $50,000.” But when they offer you two jobs for $50K times two, you’re like, “Great! Where do I sign up?!” Then you get totally burned out working 100-hour weeks, and eventually you fizzle out. People end up using drugs to get through the day—caffeine, Adderall, even cocaine. Then, they’re so wired up from their 100-hour weeks that they just drink themselves into oblivion when they get off work. It’s not a pretty system.

Now, back to your question. I’ve been saying if you want to opt out or drop out of this system, there are two aspects to doing so. One is how you relate to your courses. The other is how you relate to your time outside of your courses. Let’s just say you’re going to have a 50/50 balance between the time you spend on your courses and the time you spend on activities outside of your courses. The people who are on the “track” probably have more of an 80/20, 90/10, or even a 100/0 balance between academics and extracurriculars. But let’s say you’re going to do 50/50. My argument is that you should take an entrepreneurial approach to the 50% of your time that you spend on classes as well. By entrepreneurial I mean, try a lot of different stuff. Seek out those quirky professors you’re really never going to get a chance to study from again. You don’t usually find those quirky professors teaching accounting and finance.

These are people who have devoted their lives to the life of the mind. You tend to find them more teaching philosophy, anthropology, or literature classes. Seek those people out. Because once you’re already here—unless you’re trying to take the “track”—how you do in your classes grade-wise, and which classes you take, aren’t going to have much of a bearing on your success. When I pitch a client on a freelance writing job, I’ve never been once asked what my GPA was. If you take this entrepreneurial path I’ve been talking about, they’re not going to ask or care very much about which college you went to, or your GPA.

Let me be clear about this. If you want to get an entry-level job at Apple, they’re going to be very concerned with which college you went to, and your GPA. But that is not an entrepreneurial job. Apple is not a startup anymore. Neither is Facebook, nor Google. If you want to get a job at a real bona-fide startup that has five, 10 or 20 employees—and is growing fast—they’re really not going to give much of a darn what your GPA is. They’re going to put a lot more emphasis on your portfolio of results you’ve achieved, as well as your speaking skills, how well you collaborate with other people, your creativity, etc.. There are all these talents you can excel at that have nothing to do with grades.

Q: I’m a 1984 graduate of the college. I’ve worked in academia, business and government. From your conversations and interviews with successful entrepreneurs, what pearls of wisdom have you gained for those of us who are over 35? I work mainly as an Italian and Portuguese medical interpreter (self-employed). What I was hoping to learn are ways that I can—not necessarily become a millionaire—but how could I find more steady employment, given that I have a family and a small child. Is there something you heard in your interviews that would apply to someone with over 20 years of experience?

M.E.: There’s a one-word answer to your question. SALES. Almost every one of these people had some experience in their early days where they got really good at selling. Whether you’re trying to sell yourself to an employer or sell your products or services to clients, the first point of contact you’ll have with someone who might give you money is through your sales process.

I’m going to assume that you’re good at what you do, because you’ve been doing it for 20 years. Your leverage point is not to get better at what you do, and it’s definitely not to get more certifications in that field. This is the #1 mistake I see. Let’s say someone has a Bachelor’s degree. They go along in their career and they do okay, and then at some point they get “stuck” in their career. The number one thing they think to do when they that happens is go back to school. If they have a BA, they get a master’s, or an MBA. If they have a master’s or an MBA, they get a PhD, or a second or third master’s or other graduate degree. That is diminishing returns. The major factor that is impacting your practical success in the world, and specifically how much people are willing to pay you, is actually not increasing your certification or your talent. You’re already good enough. The leverage point now is learning sales—learning how to communicate persuasively about what you do. I don’t mean sales in a sleazy way. I have a whole chapter in my book about how sales can really be an honest, high-integrity enterprise.

Q: I have a follow-up question. In addition to my work as a medical interpreter, I started a company in 2008 for cross-cultural training.  I’ve worked with a lot of major corporations, from Gillette and Bank of America to Phillips, Deloitte, and Ocean Spray. In the last few years these companies have decided to cut their budgets for this kind of training. So I find myself doing mostly medical interpreting. But I’m really trying to find a full-time job.

M.E.: Thanks so much for clarifying. So my answer to you before was a bit off. If you’re trying to freelance, I would say the sales thing is really important. If you’re looking for a full-time job, the one-word answer I would give you instead of sales is NETWORKING. That’s where your opportunity is. I know a business owner who has a bar in Miami, and he frequently puts out employment ads on Craigslist for bar staff. These are $8 an hour positions. He’ll frequently put out an ad and get 500 responses. And 80%-90% of those people have bachelor’s degrees.

The cattle call, “herd” way of getting a job is to buckle down, get more credentials, send out as many resumes as you can, and hope that someone will pick you. The more entrepreneurial way to do it is get the certifications you need to practice your job. Like if you want to be a surgeon, you can’t get opportunities unless you have a degree that says you’re a doctor. So whatever is the equivalent of that in your field is absolutely necessary—it’s the price of entry. But once you have that, more letters after your name and more memberships and various kinds of associations—that’s not where the juice is. The “juice” is in learning how to create opportunity for yourself through networks.