i have an idea, you probably won't use it but i'd like to talk about it nonetheless.
a "true" freelancer path for the other side, that gives a new meaning to "perhaps do something about it"
it basically starts out as a secret event that happens if you hang out with your friend at least once while you haven't chosen a job. your friend asks for help doing something basic (something like helping him with moving furniture). from then on you'll find opportunities to do more odd jobs for people. once you do a few you'll unlock a new option. "become a freelancer". with a flavor text a little something like "you've made a decent bit of cash from odd jobs, maybe even enough to actually make a living out of it. you'll probably need a balance of both *intellect*, *strength* and *charm* to progress."
from then on your main source of income will be random events that require different skills to succeed in. one day you might help fix someones computer, the other you're lifting a heavy package, and occasionally you even find an antique that you can try to sell to someone.
as you get more skilled you can buy some relevant items that allow you to access more lucrative contracts. (moving van, high end pc, etc). once you've made a bit of a name for yourself, you get a contract from a certain company, and end up seeing something you weren't meant to see.
so as it goes, you're an independent (and possibly adversarial) agent that's learned a bit more about the company than the general public.
so at this point it's a bit of a toss up on how this route could continue. maybe you start some sort of rival business, or eventually some sort of resistance group. perhaps you even engage in corporate sabotage. it's honestly up to your vision of how a route like this would go, but i thought it was an interesting idea nonetheless.
so yeah, that's my idea. i imagine you wouldn't want to have to make an entire new route in addition to the ones you've already planned, but i hope you at least liked reading this.