Accepting the job can't actually fail.
Most actions will require rolls at some level.. even in this case of accepting a job, which has a roll to see if you start automatically with extra pay or a bonus, as well as a series of rolls to see who your employer is and why in particular this position is available.
You had a roll when you were looking for a dojo because you were exploring, and there was the possibility of bad or unexpected things happening. Since you are exploring inside your own city, the possibilities for bad stuff are different than there would be elsewhere. In this case, you failed to find a dojo, found some bad stuff, the bad stuff turned out to be someone selling you something that you wouldn't have otherwise bought, which turned out to be fairly expensive but quite useful, instead of a scam or other ripoff.
Essentially, it's like you got pickpocketed again, but less bad. You've had awful luck with your exploration rolls. Buying stuff or meeting unexpected people are relatively common results when critically failing to discover what you are looking for in a city.
In general, if you have something related as an asset or have discovered something, it doesn't require rolls to do interactions with it, such as joining up or asking that person for help. You can't fail asking for this job because it was already offered, as the product of an already-successful roll. Hence you don't need another roll to be able to join up. In other circumstances it might take a roll to do something with it, like the old master might require convincing to take on a student, but in those cases I'll try to make it clear what's going on with description.
The semi-automatic nature of some of these interactions is mostly to speed up the game. Like you did fail, and got the shop encounter, and then got something sold to you. You then got a save to see how good of a shopper you were and if you could limit the damage by buying something useful, or limit the damage by negotiating a lower price or buying something cheap instead of dear. You did.. ok on that part, but not perfect.
In all cases, these interactions will stop the moment something happens that is a threat to your life. Threat to your purse, not so much.
Definitely go accept the job next. We're not going to learn enough to matter with one action, nor will a single action be likely to create a contact who would influence things much. Just accept the job, before the opportunity is lost.
You go to take the job. Li Yue is.. boring, or at least seems boring as she has a story to tell you that's contrary to that. She lives in a fairly small mansion of about twenty-ish rooms, two other servants, and two other guards. She's a merchant who normally deals with fairly ordinary trade goods inside the city, such as pottery, grain, lumber.. a variety of fairly average inexpensive goods, which she then buys and sells from one person to another in bulk. Nothing terribly unusual, and there's thousands of people in the city who work similarly.
But there's something going on here. One of her servants is dead, killed by a stabbing wound to the chest, while opening a window to air out the guest chambers. There's been a few open threats to Li Yue from her rivals, but she'd never expect that would lead to an assassination attempt, which this probably was, as the guest quarters were on the top floor.
You are offered twice the normal salary for a servant, a salary of two silvers a week. You try to negotiate it up a bit, but she discerns your lack of combat experience and doesn't offer more, although you are offered two weeks pay in advance. The job will take four of your weekly actions, as you are expected to fulfill at least some normal servant duties as well as look to her protection.
(As, thanks to the wonders of the drama dice, this situation is already life threatening, the update is stopped here so you can reconsider taking the job.)