I try not to go past half way, that way if I get stuck in a situation where I have to let the car run to warm up ex: after freezing rain and windows are all caked, then I have some leg room. Also less chance of condensation in the tank.
In the summer months I'm a bit less cautious but still make sure to fill up before the light goes on. I've had it happen a few times while driving and it sends me into a mini heart attack and I immediately get to the closest gas station. Stalling in the middle of the road would SUCK. Not only having to deal with that, but the embarrassment factor. My brother in law had it happen in the Tim Horton's drive thru. People were PISSED at him because it held up the line. It's a super shameful situation to be in.
One time after night shift I got into my car and the needle was practically at empty and I freaked out wondering how I let it go that far without noticing Was not sure what gas station would be open at that time and didn't have enough gas to start driving around so I took my chances are drove towards the one closest to my house, at least if I stall I don't have far to walk. Was like -40. They were open but their interac machine was not up and running yet, think they had just opened. So I went to the corner store nearby but their ATM was down as they had not come to put money in it yet I presume. So I asked if I can do cash back if I buy something but their limit was $20. So I bought a chocolate bar and took out 20 bucks and then carefully got as close to 20 as possible when gassing up without going over. 20 bucks of gas it not going to get you very far, but it at least gave me a bit of a buffer so I can go home and then when I leave for work I can go back to get more.
Let's just say that was quite a stressful morning lol.