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One of the most challenging aspects of any software project is estimation-- determining how long the work will take. It's so difficult, some call it a black art. That's why I highly recommend McConnell's book, Software Estimation: Demystifying the Black Art; it's the definitive work on the topic. Anyone running a software project should own a copy. If you think you don't need this book, take the estimation challenge: how good an estimator are you? How'd you do? If you're like the rest of us, you suck. At estimating, I mean. Given the uncertainty and variability around planning, it's completely appropriate that there's a game making the rounds in agile development circles called Planning Poker.