I must admit that it seems strange to be codifying jobs/careers for D&D. Universally, it's always seemed a little dumb when players ask if their characters can get work for a week or two, to earn a little money. After all, why don't they just climb into a sewer, kill a few zombies and collect a bit of coin that way?
I'm trying to move away from that sort of game thinking, though not to the point where I expect characters to get jobs. I see these rules more as a means to an end; alternatively, as a solution for any time when the characters find themselves in authority.
Let's consider the latter. The local town has just been devastated by the Wererat King, a plethora of lycanthropes and a friggin' mess o' rats. The party has helped beat them all back, but the captain of the guard is dead, the captain of the watch is dead, the burghermeister is dead, the head of the church is dead and three of the four major guildmasters are dead. The town is in shambles. The only reason why looting hasn't broken out yet is because the populace is exhausted.
So the single lead guildmaster, the deacon of the local bard's college, the former deputy magistrate and the most prominent judge left in town approach the party and ask them to take over management and administration of the town. They're asked to keep the people in check, round up troublemakers, organize supplies and rebuilding efforts, etc. In return, the town is prepared to give the players a monthly wage of 5,000 g.p. (the town treasury survived or the town has access to money they can borrow from the capital).
There are some players who would take that kind of offer - only we know that it would never really be made, because most DMs wouldn't know how to run it or what to do if the party said "Yes." So instead the townsfolk thank the players very much, give them a one-time reward of 5,000 gold and send them on their way.
Very well, the former - a means to an end. The party needs to get inside the prison but there's just no way. They try bribing a guard or the thief tries slipping inside, but both attempts fail because the prison security is just too damn tight. But then one of the players thinks, "Hey, what if one of us strips down and tries out for a job inside the prison?"
All right, let's say that's what they try. Where are your rules for that? I'm proposing this political thing, but chances are you're going to manage the problem with an arbitrary die roll . . . which is fine, it's all there is. Good, the player gets inside, pretends to be a jailer (in my world it would take a month for the job to get obtained) and then waits for an opportunity to get close to the right prisoner, or perhaps the door that would let the rest of the party inside . . .
Those would be good rules to have, right? Even if the party wasn't that interested in 'getting a job,' there are situations where having the job and getting a sense of what's going on while holding the job would be good things to track. That's why I think it's worth pursuing this thought process - because while it may fit a small niche in my sage tables, in the bigger picture it could be rebuilt by you, the reader, into something that would allow you to manage those difficult non-rule situations.
Very well, so much for the preamble.
Let's begin the issue with the character having obtained the job. I spoke on this post about getting work, which I admit isn't alternate-system friendly, but might give you some ideas. What do we do once the player has the job? Please remember that the 'job' might refer to something as huge as managing all the money in the kingdom during a time of war.
The linked post in the above paragraph also contained information about how many days in a fort-month that a character would have to work - remembering that all the positions described on that post are political jobs without a schedule. Even the apprentice was expected to work to some degree independently, as they were encouraged to search for their own raw materials, experiment, work on projects that they would present to their masters and so on. An apprentice in the medieval period worked much more like an art student than a would-be electrician - something to keep in mind. The number of days an apprentice 'worked' tended to be every day . . . so the number given by the system only refers to the number of days the apprentice worked in the shop under direct supervision.
Examine for a moment your choices about how to work at your job. I propose that there are four basic tactics that you'll employ while employed. I argue that everyone works on some refinement of the following:
1. Keep your head down. This is what's known as "the company way" - shut up, do your job, don't make waves, don't get clever, don't push yourself but do exactly as much as you need to do not to get fired. Be agreeable. The result tends to be that you stay employed at the level of your current employment, until finally you've been there so long that people treat you with all the love and affection they have for the family dog. Prior to the present two generations, this used to work beautifully if all you wanted to do was work. Unfortunately, your competence doesn't increase and neither does anything else.
2. Work Hard. Increase your output, increase your focus, take on more responsibilities, outperform your fellow and bust your ass making something right. In the present culture, this is seen as being a 'sucker,' but strangely most of your employers seem to have mastered the art of perpetual work. Disregarding the slacker insistence, hard work usually leads to greater pay and greater competence - in a medieval world it also leads to injury and other health risks (people dying in fires set by candles they knocked over while falling asleep) as well as resentment and making enemies.
3. Suck up. Screw work, make friends. It isn't what you do, it's who you do it for while on your knees making coffee. Or, to put it in medieval terms, it's all about the grease. This obviously increases your chance for reputation and promotion, the former being how you're thought of by those people above you. Working hard may grant you a bit of reputation, but sucking up to the boss will undoubtedly get your more. Sucking up, incidentally, is what you'd want to do as the jailer who wants to meet the prisoner or find which door to open. The downside is that it tends to erode competence - so that if you don't get yourself posted somewhere better, or you're not going to quit as soon as the prisoner is broken out of jail, you'll fuck up eventually - resulting in a loss of both reputation and possibly health.
4. Innovate. Figure out a completely different way to do your job. This is the long shot and it isn't for everyone. In fact, most of the time if you try to experiment on the job, you'll crash so spectacularly that people will be talking about you for months. At the same time, however, if you succeed you may change the world. Logically, this is the most risky strategy and the sort that most feel won't be worth it - remember that the consequences for this sort of thing in a very high level post tends to be public execution or a lifetime in the royal tower. Success does greatly increase competency; it may or may not increase reputation in the short run, depending on how it is viewed (many employers hate innovation). It may come with monetary rewards.
The mistake would be to think that an employee must act in accordance with only one of the above. Many do, but this is a choice. Fact is, that choice can be made every day, or every week. For game purposes, I think that every day might be a bit too often - it would slow the pace of the game down as the effects for each were rolled this often. Once every seven days of employment might be more practical. Too, once a day would mean the rewards or punishments couldn't have a high degree of importance. Every seven days might allow greater benefits or consequences; once every 30 days might add still more.
Since there is the potential for some gifted persons in high positions to work under supervision as little as 6 to 10 days every two months, linking such rolls to actual number of days worked may not be the best plan. A Lord Chancellor can fuck up more things in an hour than 5,000 apprentices can fuck up in a lifetime. That needs to be considered.
My next plan, then, is to write about consequences and rewards - and all that descends from the competence of the employee. I thought I had that in hand, but I think I may need a few days before I come back to that.