How to Become the Ideal Apprentice: Part VI

Do not think that what is hard for you to master is humanly impossible; and if it is humanly possible, consider it to be within your reach.

—Marcus Aurelius

Enter Robert Greene

The path to greatness is simple. It’s the path followed by everyone from Renaissance artists to the entrepreneurs of Silicon Valley. In writing my first four books, I immersed myself in the study these types of people—some of most powerful figures in history. Over the course of many hours of thinking, researching and writing on excellence—the last four years of which were dedicated to writing my newest book—I discerned an unmistakable formula for becoming the best. That formula is revealed in Mastery.

Today I’d like to share the first in the journey to Mastery: how to begin an apprenticeship  Throughout history, it’s always been the way that Masters acquired their education. There are many different strategies for getting yours but make no mistake: you cannot become great without mentors and masters to teach you the necessary skills of your chosen craft. And if you can accept and internalize this fundamental part of the learning process, you will be one step closer to achieving mastery yourself.

Part VI: Advance through trial and error

Growing up in a suburb of Pittsburgh, Pennsylvania, in the early 1970s, Paul Graham became fascinated with the depiction of computers in television and film. They were like electronic brains with limitless powers. In the near future, or so it seemed, you would be able to talk to your computer, and it would do everything you wanted.

In junior high school he had been admitted into a program for gifted students that provided them with the chance to work on a creative project of their choosing. Graham decided to focus his project on the school’s computer, an IBM mainframe that was used for printing out grade reports and class schedules. This was the first time he had gotten his hands on a computer, and although it was primitive and had to be programmed with punch cards, it seemed like something magical—a portal to the future.

Over the next few years, he taught himself how to program by consulting the few books then written on the subject, but mostly he learned by trial and error. Like painting on a canvas, he could see the results immediately of what he had done—and if the programming worked, it had a certain aesthetic rightness to it. The process of learning through trial and error was immensely satisfying. He could discover things on his own, without having to follow a rigid path set up by others. (This is the essence of being a “hacker.”) And the better he got at programming, the more he could make it do.

Deciding to pursue his studies further, he chose to attend Cornell University, which at the time had one of the best computer science departments in the country. Here he finally received instruction in the basic principles of programming, cleaning up many of the bad hacking habits he had developed on his own. He became intrigued by the recently developed field of artificial intelligence—the key to designing the kinds of computers he had dreamed about as a child. To be on the frontier of this new field, he applied and was accepted to the graduate school in computer science at Harvard University.

At Harvard Graham finally had to confront something about himself—he was not cut out for academia. He hated writing research papers. The university way of programming took all the fun and excitement out of it—the process of discovering through trial and error. He was a hacker at heart, one who liked to figure things out for himself. He found a fellow hacker at Harvard, Robert Morris, and together they began to explore the intricacies of the programming language Lisp. It seemed like the most potentially powerful and fluid language of them all. Understanding Lisp made you understand something essential about programming itself. It was a language suited for high-level hackers, a language specifically made for investigation and discovery.

Disillusioned with the computer science department at Harvard, Graham decided to design his own graduate school program: he would take a wide range of classes and discover what interested him the most. To his surprise, he found himself attracted to art—to painting, and to the subject of art history itself. What this meant to him was that he should follow this interest and see where it would lead. After completing his PhD at Harvard in computer science, he enrolled in the Rhode Island School of Design, then attended a painting program at the Accademia in Florence, Italy. He returned to the States broke but determined to try his hand at painting. He would pay for his lifestyle with intermittent consulting work in programming.

As the years went by, he would occasionally reflect on the course of his life. Artists in the Renaissance would go through clear-cut apprenticeships, but what could he say about his own apprenticeship? There seemed to be no real design or direction to his life. It was like the “cheesy hacks” he did in high school, patching things together, figuring things out through constant trial and error, finding out what worked by doing it. Shaping his life in this haphazard way, he learned what to avoid—academia; working for large companies; any political environment. He liked the process of making things. What really mattered to him in the end was having possibilities—being able to go in this or that direction, depending on what life presented to him. If over the years he had undergone an apprenticeship, it was almost by default.

One afternoon in 1995, he heard on the radio a story about Netscape—the company itself was touting its future and discussing how someday most businesses would be selling their products on the Internet itself, with Netscape leading the way. With his bank account getting desperately low again, yet dreading the idea of returning to another consulting job, he recruited his old hacker friend Robert Morris to help him create software for running an online business. Graham’s idea was to design a program that would run directly on the web server instead of having to be downloaded. No one had thought of this before. They would write the program in Lisp, taking advantage of the speed with which they could make changes to it. They called their business Viaweb, and it would be the first of its kind, the pioneer of online commerce. Just three years later they sold it to Yahoo! for $45 million.

In the years to come Graham would continue on the path set in his twenties, moving to where his interests and skills converged, to wherever he could see possibilities. In 2005 he gave a talk at Harvard about his experiences with Viaweb. The students, excited by his advice, pleaded with him to start up some kind of consulting firm. Intrigued by the idea, he created Y Combinator, an apprenticeship system for young entrepreneurs in technology, with his company taking a stake in each successful startup. Over the years he would refine the system, learning as he went along. In the end, Y Combinator represented his ultimate hack—something he came upon by

accident and improved through his own process of trial and error.

Each age tends to create a model of apprenticeship that is suited to the system of production that prevails at the time. In the Middle Ages, during the birth of modern capitalism and the need for quality control, the first apprenticeship system appeared, with its rigidly defined terms. With the advent of the Industrial Revolution, this model of apprenticeship became largely outmoded, but the idea behind it lived on in the form of self-apprenticeship—developing yourself from within a particular field, as Darwin did in biology. This suited the growing individualistic spirit of the time. We are now in the computer age, with computers dominating nearly all aspects of commercial life. Although there are many ways in which this could influence the concept of apprenticeship, it is the hacker approach to programming that may offer the most promising model for this new age.

The model goes like this: You want to learn as many skills as possible, following the direction that circumstances lead you to, but only if they are related to your deepest interests. Like a hacker, you value the process of self-discovery and making things that are of the highest quality. You avoid the trap of following one set career path. You are not sure where this will all lead, but you are taking full advantage of the openness of information, all of the knowledge about skills now at our disposal. You see what kind of work suits you and what you want to avoid at all cost. You move by trial and error. This is how you pass your twenties, thirties or forties. You are the programmer of this wide-ranging apprenticeship, within the loose constraints of your personal interests.

You are not wandering about because you are afraid of commitment, but because you are expanding your skill base and your possibilities. At a certain point, when you are ready to settle on something, ideas and opportunities will inevitably present themselves to you. When that happens, all of the skills you have accumulated will prove invaluable. You will be the Master at combining them in ways that are unique and suited to your individuality.

You may settle on this one place or idea for several years, accumulating in the process even more skills, then move in a slightly different direction when the time is appropriate. In this new age, those who follow a rigid, singular path in their youth often find themselves in a career dead end in their forties, or overwhelmed with boredom. The wide-ranging apprenticeship of your twenties, thirties or forties will yield the opposite—expanding possibilities as you get older.


It might be imagined that certain people in history—the naturally gifted, the geniuses—have either somehow bypassed the Apprenticeship Phase or have greatly shortened it because of their inherent brilliance. To support such an argument, people will bring up the classic examples of Mozart and Einstein, who seemed to have emerged as creative geniuses out of nowhere.

With the case of Mozart, however, it is generally agreed among classical music critics that he did not write an original and substantial piece of music until well after ten years of composing. In fact, a study of some seventy great classical composers determined that with only three exceptions, all of the composers had needed at least ten years to produce their first great work, and the exceptions had somehow managed to create theirs in nine years.

Einstein began his serious thought experiments at the age of sixteen. Ten years later he came up with his first revolutionary theory of relativity. It is impossible to quantify the time he spent honing his theoretical skills in those ten years, but is not hard to imagine him working three hours a day on this particular problem, which would yield more than 10,000 hours after a decade. What in fact separates Mozart and Einstein from others is the extreme youth with which they began their apprenticeships and the intensity with which they practiced, stemming from their total immersion in the subject. It is often the case that in our younger years we learn faster, absorb more deeply, and yet retain a kind of creative verve that tends to fade as we get older.

There are no shortcuts or ways to bypass the Apprenticeship Phase. It is the nature of the human brain to require such lengthy exposure to a field, which allows for complex skills to become deeply embedded and frees the mind up for real creative activity. The very desire to find shortcuts makes you eminently unsuited for any kind of mastery (TIM: Depends on where you look for them). There is no possible reversal to this process.

It’s like chopping down a huge tree of immense girth. You won’t accomplish it with one swing of your axe. If you keep chopping away at it, though, and do not let up, eventually, whether it wants to or not, it will suddenly topple down. When that time comes, you could round up everyone you could find and pay them to hold the tree up, but they wouldn’t be able to do it. It would still come crashing to the ground. . . . But if the woodcutter stopped after one or two strokes of his axe to ask the third son of Mr. Chang, “Why doesn’t this tree fall?” And after three or four more strokes stopped again to ask the fourth son of Mr. Li, “Why doesn’t this tree fall?” he would never succeed in felling the tree. It is no different for someone who is practicing the Way.

—Zen Master Hakuin


Did you like this article? Here are five (5) more exclusive chapters on apprenticing from Mastery, in order:

Part I

Part II

Part III

Part IV

Part V

Part VI

Robert Greene‘s newest book Mastery (view trailer) examines the lives of historical greats like Darwin, Mozart, and Henry Ford and distills the traits that made the masters. It is an excellent complement to The 4-Hour Chef. Robert also authored the massive international bestsellers The 48 Laws of PowerArt of SeductionThe 33 Strategies of War, and The 50th Law.

The Tim Ferriss Show is one of the most popular podcasts in the world with more than 900 million downloads. It has been selected for "Best of Apple Podcasts" three times, it is often the #1 interview podcast across all of Apple Podcasts, and it's been ranked #1 out of 400,000+ podcasts on many occasions. To listen to any of the past episodes for free, check out this page.