Image search for "life maps" and you will find representations like the images below. These representations are useful for their talking points, and as a review of history.

From a planning perspective, their biggest defect is that they fail to represent well the current state. Imagine asking a restaurant owner about running their operation, and getting one of the above laminated place-mats; it is not obvious what the trade-offs and decisions are or were.

Compared to a battlefield map, the life maps above do not show what the problems are and what resources are available. Without that, it becomes difficult to evaluate the path chosen: what were the pressing concerns? what options were available?

Instead of using time as the basis for the map, use a relatedness measure -- i.e. the closer two items are, the more related they are. And drawing in lines of support and arrows of defense show which elements are in opposition, and which are helping each other directly. This allows the viewer to critique both the relative arrangement and the elements' relations.

Below is a map showing the problems faced and the help available to confront them. In it, there is not much cross-support -- the career has nothing to do with any of the financial capital deployments. And why is the US Debt Spiral such a central antagonist?

Provided a periodic sketch of a life map such as this, a review of trade-offs can be made and many more critiques become available. With a more in-depth map showing actual allocations (capital and time), a review of progress and decision-making would become possible.