Just my take, but I could be wrong, as I'm asking for advice on this board as well, but...

If you are 30-something and have previous professional work experience, employers couldn't care less about your High School activities (unless you are applying for a position as a High School teacher).  That HS info, your SAT score, and even Jeopardy shouldn't be on your resume, but Jeopardy "could" be an interesting ice-breaker during an interview.

As for the positions you mentioned:

Actuary - If you excel at working alone, could be an interesting field for you.  Lots of "puzzles" to solve.

Sportswriter:  No journalism background means you'll have to start as a stringer, probably a non-paid stringer until you can demonstrate quality writing/reporting.  Additionally, what are your salary expectations?  Expect low wages unless working for newspapers in large markets.

Career Counselor: At what level?  At the HS level you will need state certification, meaning extra coursework/training.  At the professional level, you'll need contacts.  If you know any career counselors, ask them how they got started.  If needed I still have the email addresses for old contacts at Right Management.  You could send them a friendly email explaining your interest in the field and ask for advice on how to enter the field.

Academic Counselor: At what level?  At the HS level you will need state certification, meaning extra coursework/training.  At the college, you may still need extra courses.  Again, try to contact people in the field, express your interest, and inquire what skills/credentials are necessary to enter the field. 

Sales:  You have to love sales.  Don't worry about the "sleaze" end, as with solid companies, your strong business background and math skill are marketable!   

Financial Analyst:  Having worked in finance myself, loaded term.  Financial reporting for a corporation?  Financial "advisor"?    The former controller at one of my former employers started as a financial analyst, work his way up to controller, then transferred (within same company) to become the Marketing Manager for TV's, and now he's a Marketing Director with another firm.  Understanding corporate finance can lead to many career paths within an organization.

I'm surprised you didn't mention teaching, especially considering your desire for counseling.  The ability to teach math is in high demand at the HS and college level.  With an MBA, you can teach (adjunct instructor) Business/Math at the college level, something I'm currently doing.  However, you would need a PhD if you wanted a fulltime career as a college professor. 

As for those websites that test Stengths/Weaknesses to help peopple find their correct career path, I find them useless.  I've sampled many, plus I've taken the tests provided by career counseling services such as Right Management.  Each test I've taken provides a different answer.  I've had everything from a "fireman" to a "priest" to a "novelist" to a "librarian" as suggested career paths.