Don't estimate how long it will take. Instead, determine your appetite.
One of the greatest innovations from the Shape Up lifecycle is one that you can steal for your own life and work: stop doing time estimates on proposed work as the primary scheduling tool. Work, like art, is never truly done; you merely stop working on it–meaning that you’ll always face pressure to grow the scope of your proposed work beyond the original plan, regardless of how conservative it was.
Instead, Shape Up proposes that you determine your appetite: if a particular focus feels worthy of your time, how much time does it deserve? Then, based on that judgment, what can you accomplish in that time?
This flips the typical Agile-inflected judgment on its head. Rather than “we must do this project; how long will it take?”, the framing is “we’re willing to give this project six weeks; what will we do in that time?”.
There’s a magic to this. It answers tons of scope questions that would normally pressure towards growth, and it focuses the mind and the team on what matters without as much pressure to add cruft.
For your next upcoming goal, if you knew you had a hard stop to your work six weeks from now, what would you aim to do?