Estimating feels responsible and concrete, but decades of research and real-world examples show it’s systematically wrong. In this episode, we share Kahneman’s work on the planning fallacy, Flyvbjerg’s analysis of megaprojects, and our own stories of estimation gone sideways. Then we show how reference class forecasting—using past outcomes instead of guesses—creates better plans, restores trust, and helps leaders place smarter bets. Forecasting is also a central move in our Complexity Aware Planning, Estimation, and Delivery (CAPED) framework, giving organizations a reliable way to plan while managing complexity. Show notes, links, and transcript: https://www.humanizingwork.com/estimating-bad-forecasting-good-episode/ Email us with your thoughts: mailbag@humanizingwork.com Connect on LinkedIn: https://www.linkedin.com/company/humanizingwork