Underrated long-term planning [v1]

I want to write something more comprehensive about this later but starting with a quick post to gather thoughts. I tried three different approaches and none of them felt quite right. There is a lot of conflicting advice online and most of it is from 2019.

I want to write something more comprehensive about this later but starting with a quick post to gather thoughts. The trade-offs here are not obvious to me and I keep flip-flopping.