I've been doing this for over a decade, leading to loops whereby each and every place I end up ends up getting measured in terms of stated goals, and the goals as rendered by actual optimization functions/behavior. It usually doesn't take long for an organization's character to completely diverge from it's surface espoused mission. It also doesn't make one popular being the only one in the room pointing this out and articulating what generally the people up top would prefer went unarticulated.
The fact is, there is a school of thought to the rogue Philosopher/Builder. It just isn't sexy, and it probably won't bring you fame, fortune, or worldly success in the time you're in. Quite the opposite. If you have a fortune going in, it will make it smaller. If you have no fortune, it won't build it by measuring it in dollars, because it's currency is lives touched, and crises averted. You might make friends. They may lift you up when the time comes, but if you've done your job right, it isn't you who benefits, it's the world when those who's life you touched won't do, build, or support a thing meant to entrap themselves or others. It's the pursuit and love of Wisdom and it's employment in charting a course through life and the intellectual boundaries of our achievable implementation space such that we minimize creating excessive knock-on problems.
The issue though, is Philosophy in a capitalist system/market runs into the same problem the practice of Architecture(buildings) runs into in modernity. In it's original formulation, the school of Architecture was concerned with designing structures that blend into where they are built with minimal clash. The modern architect, however, is more concerned with a magnum opus that stands out. That clashes, that draws the eye, and screams "I was designed by so-and-so"! The Philosopher is pushed and told their philosophy is useless/meaningless if it doesn't make money; while the locutor is ironically being completely blind to the fact that their argument has fallen victim to an inversion of the epistemic pyramid that is the hallmark of the separation of a field of study from it's foundling stage as an offshoot or niche of Philosophy. Economists & business people in particular are notorious for this behavior.
The primary challenge of the practicing rogue philosopher in today's Age, is to reclaim verdant ground in the psyche of the masses that is fought to be claimed by the Institution's of the day to ensure the masses can even remember or imagine that institutions need not exist as they are. That they, the People are the ultimate authors of how the world should be, and that through clearly communicating, sound reasoning, and adherence to a set of morals, and recognition of the utility of an appropriate set of Ethical constraints on behavior, the world we leave to tomorrow can start off on a better footing than the day before.
In the last decade, we have completely failed in that task. The reason why is obvious. The System we live in only rewards it's own ontological perpetuation, which sets it as anathema to our raison d'etre. That's only going to be solved by playing it's game even better than everyone else, while not sacrificing the integrity to be able to still teach an ultimately liberating Philosophy that doesn't presume the ultimate legitimacy of the status quo.
If this doesn't sound like a great recruiting pitch, that's... rather the point. The rogue is an Outcast, but a necessary one. The oddity that reminds that "what is" is not "what must be".
And no one is going to pay you for that.
In the AI parlance, this is an algorithm to life that intentionally rewards taking the costlier links through a network; to maintain access to the fringes, and the ways of thinking that can only be lived when the comfort of the local optima is left behind.
Live más. Then make the System realize it isn't all it makes itself out to be in the grand scheme of things. Any school of thought that doesn't embrace it's own undoing, is just that; pretense.
