Shostack + Friends Blog Archive


Two Models of Career Planning

There’s a fascinating interview with Mark Templeton of Citrix in the New York Times. It closes with the question of advice he gives to business students:

There are two strategies for your life and career. One is paint-by-numbers and the other is connect-the-dots. I think most people remember their aunt who brought them a gift for their birthday or whatever and it was a paint-by-number set or a connect-the-dots book.

So with the paint-by-number set, you know ahead of time what it’s going to look like. Then, by contrast, with a connect-the-dots puzzle, you can only guess at what it might look like by the time you finish. And what you notice about that process is the further along you get, the more clear it becomes. It might be a beach ball, or a seal in a Sea World park or something. The speed at which you connect dots gets faster as the picture starts coming into view.

You probably get the parallel. This isn’t about what’s right and what’s wrong. This is about getting it right for you. Parents often want you to paint by numbers. They want it so badly because they have a perception that it’s lower risk, and that’s the encouragement they’re going to give you. They’re going to push you down this road, and faculty members will, too, because they want you to deliver on what they taught you. It doesn’t make it wrong; it’s just that there’s a bias in the system. You have to decide for yourself. The earlier you actually get it right for yourself, the faster and the better that picture is going to look.

And the more time you spend on paint by numbers when you’re a connect-the-dots person, and vice versa, the harder it’s going to be. (Mark Templeton, quoted in “Paint by Numbers or Connect the Dots“)

When I got started in information security, there were a lot fewer jobs. They were less categorized. There might have been degrees in information security, but there certainly were not “Centers of Excellence” churning out graduates. (It turns out “degree” is one of those terms, like “hotel” or “mesothelioma” that’s so heavily SEO’d that it’s a pain to search that history.) Because there was no “paint by numbers” path, people entered the field from a wide variety of backgrounds. Everyone was connecting the dots as we went.

Anyway, I like the analogy, and think it explains why a lot of career advice fails to help its intended recipients.

3 comments on "Two Models of Career Planning"

  • Jeff Combs says:

    As someone who has been directly involved with helping people define their careers in infosec, I think your analogy is especially true of the pioneers in our industry. If I look back on the thousands of conversations I’ve had with infosec people over the years, there’s an overwhelming majority of people who couldn’t follow the template and started painting outside the lines. At it’s core, infosec requires the ability to look at things from a different angle and follow paths that could just as easily get you lost. And mix metaphors.

    While I think there can be value in education and following a program, it’s the dropouts and the artists and the musicians and those who struggle to follow directions that usually push the needle furthest.

  • Chris says:

    “Connect-the-dots”? Put me down for “random walk” ;^)

  • cc says:

    Reminds me of mappers vs. packers:

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