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Financial planning often doesn’t take place on a beach. But the next time you find yourself there, try this experiment, courtesy of management and motivational guru Stephen R. Covey: You’ll need a mason jar and an assortment of big rocks, smaller gravel, sand, and water.

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Maybe your middle schooler is already hip to saving. Many kids this age do chores and earn allowances, perhaps putting part of what they earn into a savings account for college....