Forecasting (outcomes, benefits, risks) is fundamental to investing wisely. Most of us just don't get the practice and particularly not the rapid feedback.
The weather forecasting fraternity have used the Brier score for years to drive improvements. It judges how realistic you were in expressing your confidence by the width of your forecast range. Once you can measure your ability to estimate, you can train to improve that ability.
A presentation I delivered to the Enterprise & Solution Architecture meetup group in Auckland. IT Architects have to estimate many things at an early stage of development, when the cone of uncertainty is widest. This presentation suggests ways in which architects and other early-stage estimators can estimate both cost and value, systematically reducing the uncertainty.
Knowledge comes by taking things apart. But wisdom comes by putting things together. - John A. Morrison