I enjoy the Histories in BREAK!! being a mix of lifestyles.
The last edition of D&D is probably the game most people have played that involved some kind of history/background mechanic, although I think we can all name some games where that's a much bigger factor. I think something that got missed in the way people treated those was that the initial PHB offerings were effectively all reasons one might travel. Even the Hermit: they lived a secluded live, discovered some secret or insight, and are out in the world now spreading that around. Over time this remained mostly true even if the became more tied to specific careers and experiences, a mix of superhero origin story and CV. In a world where you're constantly beset by giant beasts, ghoulies, magic monsters etc, the average NPC leads their life in one place.... content with their lot and awaiting a wandering party to fix their problems. When the world is wild, civilization is small.
BREAK!!, on the other hand, is not terribly wild at all. There are places OF wildness, and places where time has gouged deep wounds into the world, but the world is largely known and "mapped" such that there are few places to leave blank for "here be dragons." Indeed, BREAK!!'s map indicates explicitly where there WERE dragons... What great nations and city-states exist do so with something approaching a modern awareness of one another that recalls at least the European colonial era if not late Victorian explorer accounts. Folks in Berry Town may have heard that the junkers of Stahlfield eat babies but they know where they are and what their overall deal is apart from those rumors, at least. One scholar of ancient culture I read in college had a definition of civilization as the point where a shared language is adopted, and since Low Speech is baked into the Outer World and spoken by all sapient things one could argue for BREAK!! being among the most civilized and connected fantasy settings on the market....
The Histories on offer do have some typical genre conventions (e.g. Knight Errant, Street Rat) but they're typically very specific and very tied to the demands and expectations of their associated regions. Some denote training, some denote upbringing, and some denote circumstances, but whereas I think a lot of D&D5's Background were designed from the perspective of "Why have you found yourself on the road in an adventuring party?" as if being "an adventurer" is something you can just fall into, BREAK!!'s Histories seem more designed around what your character would be doing if they weren't ON AN ADVENTURE. Tom Hanks used to be a teacher in Saving Private Ryan and that does inform his character and his behavior when you know that, but it's wildly different from how everyone in his command pictures him. He's on an adventure because of a convergence of unique circumstances, some of which arose our of necessity and some of which seem almost contrived against him. He's going to go back there some day, just like Gonzo the Great. There are others in his company who feel differently, who can't wait to leave their old life behind and use the money and experience from their military service as a launchpad into something new, something better than the circumstances they left behind.
That's because the Histories in BREAK!! represent a choice. There are some folks bopping around doing good deeds because it's what they've run towards, and there are others for whom these wonders and horrors are only something to run THROUGH. Sometimes the choices are easier than others: someone devoted to "vanquishing all evil" after a life of pious service will find being a vagabond savior a smooth, imperceptible transition. A merchant or craftsman might easily find opportunities to ply their trade during travels, or might commit to this new way of life precisely because of the opportunities it affords them for when they elect to walk away. That's life, though: depending upon our circumstances and resources, some lifestyles might make some choices easier or much much harder depending on the person.
But it is a choice. That's why they're Histories and not Backgrounds. Do you long for the Shire and wish you'd never left, or do you embrace the riches and spectacle that you've found walking man's road: your past or your present? Known or unknown? You have to reconcile it somehow to have any future worth speaking about at all.
