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Apprenticeship Patterns by Adewale Oshineye, Dave Hoover

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Draw Your Own Map

Beware of the detractors. We might come across situations or colleagues or people in the society who will try to prove that programming...will become an unsustainable activity as time passes by. They think software development is only for fresh graduates...and when we get married and have kids we cannot do that anymore.

Mohan Radhakrishnan, comment [20]


Any given employer can offer only a limited subset of all possible career paths.


None of the career paths that your employer provides fits for you.


Identify a logical but ambitious next step for your career. Understand that it’s not up to your employer, your career counselor, or your professors to give you a hand up. Arriving at your next step and charting the course to ultimately arrive at your ideal destination is your responsibility. With your next career step identified, visualize the smaller, interim steps you need to take to move forward.

It is vitally important that you take the first step even if it doesn’t seem that significant. That first step will generate the momentum that will help carry you toward your goals. It’s the willingness to take that first terrifying step (and all the other steps later on), even in the absence of a perfect plan, that turns your map from a daydream into reality.

Rather than simply writing down high-level goals, try to define small, achievable steps. These small steps will provide feedback that you can use to modify your map, but they also make it easier to get help from Kindred Spirits to achieve your goals. After all, there’s not much anybody else can do to help you become what Paul Graham calls “a great hacker,” but they can point you toward resources that will help you learn Lisp or Unix socket programming or achieve similarly well-defined goals.

If you find that your vision of yourself is not in accord with your employer’s vision for you, and there doesn’t seem to be a way to reconcile the differences, examine other opportunities to see if they’re heading in the desired direction. Remember, there isn’t one single path that all apprentices follow. Instead, successful apprentices follow paths that share a certain family resemblance. These resemblances do not happen because apprentices are inexorably shepherded into making the same decisions by their mentors. They happen because each apprentice, consciously or not, chooses their route through life based on an overlapping set of values.

You should continuously reassess your map as your circumstances and values change. Sometimes your map will be in accord with that of those around you, and sometimes your map will require you to chart your own path through the wilderness. Some apprentices we’ve spoken to have found that being open about their current map has enabled them to find Kindred Spirits while maintaining healthy relationships with current and past employers. The only constant is that the map is always yours, and you’re free to redraw it at any time.

Use Sustainable Motivations and Use Your Title to prevent your current title and salary from narrowing the possible destinations on your map. If you need to move into a less hierarchically impressive role in order to stay “on the map,” consider The Long Road and compare the relative importance of impressive (short-term) titles and salaries to working in a company that is more congruent with your goals and will lead you greater heights in the long term.

These stories point to Desi and Chris’s priorities. They weren’t going to allow a company’s expectations or culture to stand in the way of achieving their goal of becoming a better programmer. These stories are particularly appropriate for system administrators and testing professionals who aspire to become developers. Too many organizations pigeonhole people and take a short-sighted approach to their personnel (or “resources”). Thinking of Desi as simply “a sysadmin” is easier to manage than realizing that Desi is a person who aspires to become a great programmer. Some organizations will be able to rally behind the audacious goals their people set for themselves. Other organizations choose not to. If this is the case at your organization, you need to begin to look elsewhere by Expanding Your Bandwidth and Finding Mentors who can provide guidance.


List three jobs that you think you could do following your current one. Then list three jobs each of those could lead to. Take a hard look at all 12 jobs. Is this really the full range of desirable jobs for the next few years of your life? Is there something missing? Extend this diagram by adding three jobs for each of the nine jobs you recently added. This should increase the number of jobs in your diagram by 27. Ask yourself if this set of jobs is more representative of the range of career options you have and the places you want to take your career. What are the constraints that are limiting your options?

If you’re unhappy with the diagram so far, repeat the exercise with different jobs, perhaps in different business or technology domains. Then try the exercise yet again and see what happens if you relax one of the constraints that you’ve always accepted. What if you become willing to move to another country, get a new qualification, or learn a new human/programming language? What if you were to start your own business? What if that business merely used software as a means to an end? There are more possibilities than you might think.

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