The Heavy Responsibilty of Advice

Yesterday a student asked me for advice. Usually the questions from students are vague and about money.
Questions asked by students in general are as follow: 
How can I become rich?" or "How should I invest?"
My answer to the above questions are "Save and do not spend" and "Diversify your investments portfolio and do not panic when one of your investments goes down because some other part of your portfolio is going up!" (followed by this is the beauty of Diversification).  These questions and the advice are ones that I follow and are are standard answers and to a certain extent accurate.
However, yesterdays question did not leave any room for me to be general and/or vague. My heart broke for this student. Yes some economist scape graduate school with their hearts intact!
The question from the student was as follow:
 "I have a bachelor degree in mechanical engineering and am offered a job in Alaska drilling for oil"
I congratulated the student and asked when will he/she be leaving. I assumed that the student wanted to drop the class or take the exams earlier.
However, the student was not sure if he/she should take the job. The student worried about his/her mother worrying about his/her safety. Also the student explained to me that his/her father expects him/her to take over the family business as the eldest. The father is still relatively young and it will be a few years before the business is handed over to this student.  
The student was worried about his/her mother's feelings, a father's expectations and his/her own future.
I was trapped. I could not give one of my general economics answers with the on one hand but 'on the other hand'. This was very specific and as time went by it became more and more specific.  The weight of giving the correct advice was growing on my shoulder. I wanted to run away screaming because I was being pulled into the realm of Dr. Freud with 'my father makes me feel this' and 'my mother makes me feel that' . However, I did not have the heart to do that with a student who is taking a chance and spilling all of his/her problems to me. 
Before the student could drag me down deeper into the land of Freud, I gave the same advice flight attendants give: "put on your own oxygen mask first before helping your companions" in other words "take care of your future first and then worry about how it affects your father and mother."
I recovered into econland and told the student the longer you are out of the job market the harder it is to get a job. I recommended that he/she accepts the job in Alaska because statistically it is easier to get a job when one has a job. The student was still worried about his/her parents. Based on the description of the father provided by this student as a demanding father with high expectations of his children, I pointed out that the father would be proud of him/her standing on his/her own two feet. Also he/she can repay his/her student loans since the job in Alaska pays for room and board. The student will be able to save and build a small nest egg. I did not have an answer for how this student can calm the overprotective mother's fears.
Last night I could not sleep. I kept worrying that this mother's worst fears of Alaska may come true.