One or two people mentioned it here, but it's all about the comfort level. I remember when I first started riding I would just keep it in the neighborhood, practice, etc. And then one day I just felt like expanding a bit and rode to a friend's job, and after that I never really looked back.
I remember summers and summers ago one of the CSC guys who was a MSF instructor offered the "advanced rider" class for free to a bunch of us. He said something that I never forgot and think about every time before I sit on a bike, every single ride I take whether it's doing "townie" crap like going to the store or going for a weekend ride in the hills -- and what he said was that you never want to ride over 70% of your ability, so that you always have a margin of error to compensate with when something goes wrong. The trick is knowing that every day you get on a bike your ability level changes, and part of becoming an experienced rider is learning how to quickly gauge where you are that day.
The best advice I could give a new rider thinking about this question is to learn at the pace you feel comfortable with and never, ever, succumb to peer pressure while riding. Every summer I've been in this club there's been at least 1 crash because someone didn't realize that just because the person in front of you could do something it doesn't neccesarily mean that you can, or felt they had to keep up and didn't have the skill, etc. And unfortunately in this sport being wrong is rarely a casual learning experience. Learn the basic skills so that driving the bike becomes second nature, THEN start applying it to the more difficult things (weather, bad pavement, high traffic). Trying to learn things with a trial-by-fire type mentality is not only stupid on a bike, it's a good way to get hurt.
Secondly, never be afraid to ask for help -- I know personally I'm more than willing to spend an afternoon with someone new in a parking lot (and have done this before with some riders) or going around town or up to the hills helping them find lines, kill bad habits and learn, and I'd bet there are plenty of riders all around town here who would do the same ... ASK! That's one of the benefits of the CSC, we're a friendly bunch. And I think I can speak for every member when I say we'd much rather see a thread asking for someone to spend a few hours helping a new rider then read a thread about how someone's in the hospital. Or worse.
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