I did some extensive drilling on a 10 gallon. Be the tortoise, not the hare. Slow, lots of water to cool the bit. Lots and lots of water. I marked my cut with marker, used tape on both sides of the glass, and used a diamond tipped Dremel bit to cut slots for an external overflow and holes for returns.
I did break one tank, because I wasn't patient and pressed too hard with the Dremel. As long as the glass isn't tempered, and you take your time, especially when you get close to breaking thru, you'll be fine.
Practicing on a 10 gallon isn't a bad idea. It's a lot cheaper than a mistake on your running tank, and far less forgiving - an ideal training environment. If you can drill a 10 without breaking it, you'll be confident, comfortable, and competent when it comes to cutting your existing tank.