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Like every mantra or cliché, taken to its extreme a piece of advice can be not just meaningless but possibly even dangerous. We’ve all been on trips where there’s been too much planning and suddenly the trip becomes more like a board game and less like vacation. Some trips are best left too spontaneity but those are often short and quick. For the big trips, you need to plan. And the same can be said for goals, the bigger the goal the more you need to plan. Like what you want to be when you grow up. You can leave that to chance, let the wind blow you where it will and hope you end up in paradise. Yeah, right. The trip that leads to the career of your dreams needs a plan; something comprehensive that’s created early and revisited often. In short, something none of us like to do.

We’ve taken different approach to all this planning. We’ve made it more like a trip or a journey – because this really is a trip. Travelers will tell you that it’s impossible to get to Bermuda without taking a boat or a plane; likewise you can’t become a doctor without getting a degree. The trip it will take to earn that degree is up to you; and it’s often the best part. But it’s a lot easier with a plan. So here’s our less-serious guide to the planning for career you want. And believe it or not, that planning starts as early as kindergarten. But never fear, the first eight years are easy. We’ll be drilling down and measuring up later; for now, enjoy this.

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