I think a mistake was made when points and estimation came together. There is some history there and lots of debate. What I've landed on is points are good at d

I think a mistake was made when points and estimation came together. There is some history there and lots of debate. What I've landed on is points are good at driving a conversation around "should this story/ticket be broken down into something more manageable that still delivers value?" With that as a guide post, our team only points stories as 1, 2, or 3. 1 is "we know exactly how to do this straight forward thing." 2 is "we have some figuring out to do, but think we can do the thing in a reasonable amount of time and effort." 3 is "there are some big unknowns, but we can't think of a way to break this into smaller, useful chunks." If the team points a story as 3, it is a flag that we need to talk about it and figure out if we can break it up. We usually can. For estimation of work we can pull in, it is about letting the org know when they might expect things. We pull in our average number of points minus a buffer, and then will pull extra things in as needed. But by committing to less, we are more likely to deliver what we said we would. That keeps the org happy. For long term planning, I think points fall apart. The best I know to do is list out all the things that likely need to happen, break them up into stories/tasks, and make an educated guess and add padding for the unexpected and padding for optimism. And remember Hofstadter's Law: It always takes longer than you expect, even when you take into account Hofstadter's Law.