Do you play it safe or push your limits?

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This is coming from a school-related place for me. In all other areas of life, I am probably someone to play it safe - change is scary! I am three weeks away from successfully finishing my first semester back in college, with all A's except for one B! I feel pretty accomplished, although there is quite a bit to do yet before the term finishes (finals, papers, etc), but I have been juggling working full-time, going to school full-time (13 credits), working a 2nd (limited) part time job, and also volunteering for two different non-profits when I can. It feels good! Now I am signing up for next semesters' classes, and I am trying to decide on whether I should really TEST myself or play it easy. This semester I am taking 4 classes, which accounts for 13 credits. I am debating on next semester taking 5 classes, worth 16 credits. I would like to do this because I want to get it "over with" as soon as possible. Hate to say it like that, but as soon as I finish my generals I can start doing my major work - which is the purpose of college (in my opinion that is!). It will cost me about $700 more out of pocket, but I am thinking I can come up with it, using their monthly payment plan. I think with doing this extra class, I will basically only have to take math and science (1 class each) in order to move onto my generals, and I could probably do those over the summer. I am just afraid that if I get too overwhelmed, and I fail one or more of the classes, that $700 (or more) is going to come out of my pocket and go to waste. There is a withdrawal period, I think of about 1 1/2 months after the semester starts. So I could technically try it, for a month and a half without being committed to paying for it, and back out of one of my classes if I thought it was too much. What would you do in this situation?