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Apprenticeship Patterns by Adewale Oshineye, Dave Hoover

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Chapter 3. Walking the Long Road

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It’s not just a question of conquering a summit previously unknown, but of tracing, step by step, a new pathway to it.

Gustav Mahler, musician and composer

Do you have training and achievement certificates hanging around your cubicle? Back when Dave had his very own cube and even less experience than he does now, he conspicuously piled a stack of certificates near his desk. The pile featured a Brainbench “master” certification in Perl and grew to include certificates proving that he had completed various multiday trainings in C, J2EE, Vignette, and ATG Dynamo. This small stack of pseudoparchment reassured him (and his organization) that he knew what he was doing. He had been “trained.”

Meanwhile, Dave had started to branch out and connect with the broader developer community through http://perlmonks.org and the comp.lang.perl.* newsgroups. It was in these groups that he discovered some exceptional Perl hackers. The hackers’ expertise was daunting, particularly because Dave could see that they were still learning, and fast. It began to dawn on him that he had barely scratched the surface of what it meant to be a great software developer. Over the following months, his pile of training certificates slowly disappeared beneath a larger pile of scratch paper and printouts of book drafts and tutorials.

Through his observations and interactions with a few of these exceptional hackers, Dave was captured by the learning process. Periodically he would catch a glimpse of the depth and breadth of the hackers’ knowledge and come away either discouraged or inspired—discouraged by how little he understood, yet inspired by the power of these hackers’ abilities. He threw himself into side projects and began to read anything he could get his hands on.

The more Dave learned, the more he recognized how far he had to go. Over the next few years he had the good fortune to collaborate face-to-face with some exceptional software developers. Dave saw that although these exceptional people were miles ahead of him, they were all walking the same road.

The Long Road

“How long will it take to master aikido?” a prospective student asks. “How long do you expect to live?” is the only respectable response.

George Leonard, Mastery

To become truly good at programming is a life’s work, an ongoing enterprise of learning and practicing.

Ron Jeffries et al., Extreme Programming Installed

For every step you take toward mastery, your destination moves two steps further away. Embrace mastery as a lifelong endeavor. Learn to love the journey.

George Leonard, Mastery


We live in a culture that values overnight celebrity, rising stars, material wealth, and quick results. There are very few programmers around who can tell you what software development used to be like back in the old days. When you do speak to these veterans, they shake their heads at the latest industry fad that is repeating the mistakes they saw in their youth. The lessons appear to have been forgotten because there is so little knowledge transferred between generations of software developers.


You aspire to become a master software craftsman, yet your aspiration conflicts with what people expect from you. Conventional wisdom tells you to take the highest-paying job and the first promotion you can get your hands on, to stop programming and get onto more important work rather than slowly building up your skills.


First, accept the fact that you may be considered a bit strange for what you want to become. Second, keep your focus on the long term. During your apprenticeship, value learning and long-term growth opportunities over salary and traditional notions of leadership.

People aspiring to become masters of software craftsmanship need to plan for the long term. This long (yet bright) journey will bring you a rich set of abilities. You will become skilled at learning, problem solving, and developing strong relationships with your customers. You will come to wield knowledge and technology as the samurai uses his short and long swords. You will come to comprehend and appreciate the deeper truths of software development. But all this will take time.

You should be prepared for the length of this journey. When you Draw Your Own Map, you should keep in mind the expectation that you will be a working software developer even when you are middle-aged. Let this influence the jobs you take and the scope of your ambitions. If you’re still going to be working in 20 years’ time, then you can do anything. No one is so far ahead that you can’t match their skill level given the decades you will have to hone your craft. No business or technical domain is closed to you. With an entire career devoted to the craft, it becomes realistic rather than vain to think about surpassing people like Donald Knuth or Linus Torvalds. The length of the journey merely multiplies the possibilities that are open to you. (Of course, people like Knuth and Torvalds won’t be staying still whilst you catch up to them!)

This pattern is not for people aspiring to become CIOs or project managers, or filthy rich. Along the way, it is not unlikely that you will take on roles of power and responsibility or find yourself quite wealthy. However, these roles and benefits are not the main motivation of the successful apprentice—they are merely by-products of a lifelong journey. And rather than counting the days to retirement, the craftsman will willingly and joyfully work into her final decades.

We don’t want to give the impression that everyone must follow a single road (see Draw Your Own Map) or that this is the right road for every software developer (see A Different Road). Some people leave development permanently and become executives, testers, salespeople, or project managers. Some people leave technology permanently and enter into entirely different fields. These are all valid and beneficial roads to take, but this book and this pattern are not for those people.

If an Accurate Self-Assessment is the cornerstone of a successful apprenticeship, then The Long Road is the foundation. The transition from apprentice to journeyman is only the first of many steps along the path to mastery. Like a martial artist attaining the rank of black belt, a new journeyman realizes how much farther he has to go.

Software developers are fortunate. Ours is a complex and profound path, a path that by its nature changes continually. Moore’s Law marches relentlessly on, regularly opening up new opportunities for craftsmen to explore new platforms or reprioritize the characteristics of an established program. And yet, other changes are often superficial. New technologies replace older technologies, yet solve the same fundamental problems. While there will always be new software to learn and better hardware just around the corner, The Long Road teaches craftsmen the deeper truths of the craft, allowing the masters to transcend specific technologies and cut to the heart of the problem.


Close your eyes and imagine the strangest possible role you could be playing in 10 years’ time. Have fun thinking of the wackiest possible future for yourself. Then think about 20, 30, and 40 years from now. What kinds of experiences do you want to have tried? Imagine that 40 years from now you are asked to write a short description of your professional history and the biggest influences on your path. Use the output from that thought experiment to help you plan your future career choices.

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