Exactly how many times are you going to have to explain this?
And woah, hey, that’s just mean.
Let’s get down to business though.
Delivering the letter, and promptly getting the response back to Quill-Weave.
The best course of action to complete that task:
There’s no telling what kind of danger lies among those ruins. Sure, you may find something of value, but you may also get eviscerated by a monster. You’re not an experienced traveler; should danger arise, you have no experience in defending yourself. If you ran into trouble, it would be big trouble. You were told it was safest to stay on the path.
You’ve had setbacks, sure, but you still have Quill-Weave’s letter. You lost her potion and you lost her money, but you can still deliver this letter and return with the response. You may have to sleep on the cold streets of Kvatch, but you can do it.
You understand that.
You know you’re not going to advance much from doing this, but it will be a small start. It will be one person you haven’t completely failed.
And you know that she’ll still be disappointed in you. She gave you a simple job out of pity, and you’re going to come back in more debt than when you left. When you kept Gharug’s money a secret, you were hoping you could surprise her. Show her that not only could you do everything she asked, but you could do more. You could be something special. Someone special, who goes above and beyond. But now it’s just like Lelles’ said: your “best” is slightly worse than everyone else’s “average”. And it hurts, trudging through the job knowing that your only goal is to minimize the inevitable disappointment.
Maybe you’ll have some opportunities to get money in Kvatch. More of the same: jobs you don’t have the skills to accomplish, given to you by people who know you’re worthless. More people to disappoint, uncomfortably agreeing to pay you one coin for your failed efforts. Here you’re nothing more than a homeless slut begging for work. You should’ve just stayed back in Hammerfell as that trashy Khajiit whose own family didn’t even believe in her. At least there, you had a home. At least there, they were used to you letting them down.
You don’t know if you’d find anything valuable in those ruins. Maybe you’d find a treasure that would solve all your problems; enough to let you return triumphantly to Quill-Weave with a response letter, new book, and a contractor to fix her windows. Maybe you’d find a monster that’d make Gharug look like a lightweight. You know with every ounce of your being that you should take that step toward Kvatch. But you also know that, should you turn back to those ruins, there’s one thing you are guaranteed to find:
Maybe only for a fleeting moment, until you find them empty or get devoured by a monster. But for that one moment, you know there is a chance you could fix everything. A chance for you to do more than mitigate damages to an already failed quest. You could do something you’ve never done before; something you’ve never failed at. Your whole body feels heavy as you begin to walk toward Kvatch.
… but when you take that experimental step backwards toward the mysterious ruins, toward the unknown, you feel light as a feather.
You’re going to play this safe, plan ahead, take precautions, and check them out. And then in one hour, you’re going to continue to Kvatch.