Some problems in philosophy and life are like jigsaw puzzles. Visualizing the bigger picture can be more helpful than analyzing the individual pieces in isolation. The more the imagined picture approximates the real one, the easier it becomes to connect the pieces together.
There are those who already have some sort of incomplete picture of the world and what ought to be done in it and are either actively or passively alert for any missing pieces of the puzzle. Then there are those who don’t really have a big picture, and merely respond to the urgent demands of life, connecting pieces in whatever way seems to work for the time being given the pressures of modern life. Both groups, though the latter perhaps more often than the former, sometimes connect puzzle pieces that seem compatible but don’t really constitute any coherent or comprehensive picture of reality and might even later unwittingly sabotage their own ideals, plans and aspirations or those of others they care about.
Throughout history there have been many pictures and stories as to what the world is, how it came to be, where it is going, and what is our role in it, if any. Some of them have become both the map and compass for directing the lives of millions of people. Others have been abandoned, forgotten or labeled as outdated for directing contemporary life.

Philosophical Cartography

Philosophical cartography tries to create or retrieve maps, diagrams, missing puzzle pieces, games, software, pictures, stories and metaphors that aid in understanding and navigating existence. The motive and starting point is simple: existence is complicated, knowing what the world is and what, if anything, we ought to be doing in it, isn’t easy. Aids that make it easier to navigate existence without watering it down to the point where we drown in falsehood can prove extremely valuable. If their use also forms us to the point where they become unnecessary so much the better.

Quentin Skinner’s Genealogy of Liberty diagram

Skinner's Genealogy of Liberty Diagram

The creation of any such aids inevitably involves certain initial decisions with respect to how they are going to be designed and what’s going to be included and excluded from them. For example, Quentin Skinner, the creator of the philosophical diagram above1 depicting a genealogy of liberty, stated explicitly in his lecture that we ought to keep in mind that his exposition draws almost exclusively from the Anglophone tradition in political philosophy. A diagram that tried to include additional traditions might have looked very different.
Therefore users of such aids are advised to never forget that those decisions made on crossroads of judgment2 by those who made the aids could prove to be bad ones, as any philosophical cartographer is susceptible to human ignorance and prone to error, or simply unsuitable for certain circumstances or purposes.
Because of the very awareness of human ignorance and fallibility, philosophical cartographers understand that the function of some of their aids can at times be more formative than informative. Though aids often aim at accuracy and comprehensiveness sometimes maps, puzzle pieces, games, pictures, stories and metaphors serve more as heuristic tools, aids to discovery, rather than accurate and comprehensive representations of reality. They are like Wittgenstein’s ladder or the raft parable in Buddhism.
The difference between an ideologist and a philosophical cartographer is that between someone who describes a terrain but only in so far as it pertains to the direction that he wants you to go and someone whose priority is describing the terrain and all the possible paths in it. Of course, as already mentioned, it is impossible to avoid the possibility that through some design decisions certain descriptions of a terrain, unbeknownst to the philosophical cartographer, may favor certain paths more than others, however the proper intention behind the creations of a philosophical cartographer is not to limit perception and curtail freedom of choice but on the contrary to augment it by revealing previously unknown or forgotten possibilities of existence without shying away from showing how certain paths lead to contradictions, catastrophes or dead ends.
Ideally, philosophical cartographers aim to make their aids in such a way that their form is distinct enough that anyone wishing to use them can easily ditch or remix their content and still derive some benefit.
For example, the aid below remains agnostic with respect to the actual contents of the left (reality) and the right (belief) categories. It only invites us to think about the significance of potential discrepancies between the two sides and their subcategories.

Reality & Belief

Reality & Belief Figure

The subcategories (e.g. “What I believe I am”) in the figure are meant to be illustrative rather than exhaustive. I included other people3 to invite the viewer to consider and reflect upon the fact that we constitute our worldview not only in reference to ourselves and the world but also in reference to other people in it.

Philosophical Exploration and Cartography

It is hard to be a philosophical cartographer if you’re not also a philosophical explorer. For how will you map the terrains of the soul if you have not traversed them yourself? Relying on second hand accounts and hearsay is usually insufficient, though at times collaboration between meticulous explorers and fastidious cartographers may yield a good result.
Philosophical exploration, just like geographical exploration, is not without its dangers. In order to discover the outer edges of experience and thought, philosophical explorers, like Socrates, Nietzsche and Camus, can end up in fatal proximity to madness, solitude or death. Though explorers will not choose to stay in every place explored, a part of every place may choose to stay with them4.
Cartographers who used to be explorers frequently provide the most helpful maps in avoiding dangers they often couldn’t avoid themselves. Perhaps they feel compelled to provide such maps to posterity in the hope that future explorers will avoid known pitfalls and reach deeper into uncharted territories faster than their predecessors.
Just like philosophical exploration is not without its dangers, it is also not without its glories. For every now and then, the effort in lifting the burden of the rock of ignorance we all carry but few push up the mountain of truth, lights a fire within, that provides the strength necessary to push it all the way to the top and finally gaze at exotic landscapes that explain and fulfill our greatest aspirations. It matters little if most of the time you go up and down like Sisyphus, for every now and then you return like Prometheus, carrying the fire of a new happiness5.