Thinking outside the lunch box is probably the best way of getting anything good inside it.
Lunch is more fun if you think pragmatically. You don't have to have seen Monty Python's "The Meaning of Life" to know not to pack items that might pose a health risk. Avoid fragile things like delicate cookies and, yes, potato chips. Don't dress salads in advance -- carry a container of dressing separately -- and don't pre-cut fruits or vegetables that will brown or dry out -- pack them whole and include a paring knife.
Even if you use a Thermos, don't include items that need to be served very hot or very cold. And think about how the components of the meal work together over time: Very few dishes taste better when they're soggy.
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