Why are we, as software developers, so bad at estimating how much work a new feature will take? For years I tried to avoid giving estimates because I was “bad at it” and it was “always wrong anyway”. But as a technical co-founder or a business owner, you need to know. We can do better than in the past! Lets understand *why* it is so hard and what has been tripping us up. I introduce an approach that’s been around a long time in other areas but we don’t see being applied to software. Lets find out *how* to apply this approach to our **existing Agile methodologies** and the way modern teams work today. Finally I introduce an OpenSource tool created for software developers that helps us make better estimates. If you can move text around using your favorite editor, then you can do it too. Using a Markdown-based tool, start giving better estimates and tracking your progress and improvement for your own benefit.