Thank you all for your advice so far. I've been discussing this with the significant people in my life, and one of them mentioned to make sure that selling the stock wasn't going to cost more than the 10% discount. My company's site says, "You will be responsible for transaction fees related to the sale as well as any capital gains taxes due on earnings from the sale." So I wanted to know how much the transaction fees might be, and how to calculate capital gains taxes. I spoke with the company that will manage the sale, and they couldn't give me exact numbers(which I found a bit frustrating), but said, there is a 29.95 transaction fee + $.05/share+the SEC which is between $.01 and $1. So calculating it out, is there a point where purchasing shares would not be beneficial? I calculated the general cost, based on current share price(about $68/share), and a guestimate of how many shares I think I will be buying(it could be more, could be less, depends on my hours, which fluctuate) and come up with about 35 shares. So if my math is right, when I sell, transaction fees will be about $32-33. All constant, I should still come out with about 200 more than I would have without this stock option program, which isn't bad(for 3 months) I suppose. Is my math right? And how do I calculate the capital gains tax? If I don't leave it there, but sell it the day it comes out, and then invest it in an index, will I have to pay capital gains?