Midlife methods

I would like to find a new career path and would love to use machine learning systems to help me make a few decisions.

Should I create a corpus containing 10 years of emails and personal documents and compare it to potential positions? What systems or methods would you use?

Initially I was thinking about a sentiment/polarity analysis to determine what I'm the most happy doing then comparing the top results to positions/careers.

I'm sure there are much better ways to go about this, does anyone have insight?

If you know of a specific text you think I should review please let me know, I'm happy to research I just don't know where to start.

Thanks all!

Edits:

I intend to look for the most positive sentiments in my corpus and match it against position descriptions. The thinking being that what I'm the happiest talking about would be what I would enjoy doing full time. I do apologize for being vague, it's not a form of laziness it's a lack of experience.