Shortly after any new idea, the inevitable query, "how long will this take?" is sure to follow. We hope that this question sparks an analytical estimate of the work involved and the effort required, but for some of you, this question may only rekindle images of your last project's death march, where an unrealistic deadline was foisted on you. In this Advisor, we look at the estimation process and some approaches for mitigating a few of its inherent challenges.