I've written about this before, but it can't be overemphasized: People can only be as generous as you allow them to be. When you gently ask for something, it will be given to you in most cases. If you refuse to accept help, it is impossible to lend a hand. So on our way towards a generous society we need to become comfortable with demanding more. If it's simply too much we should accept "no" and also be able to say "no" when being asked for something we don't want to do.
Take this odd example: You're out of money, hungry and some stranger in the city's got a pizza. There is nothing wrong in saying the truth: "I'm extremely hungry, but I forgot my purse at home. Would you mind giving me one slice of your pizza?". If the stranger doesn't want to share, it's totally fine. But how can somebody know that you need his or her help if you don't say it? I think it's not bold to be honest. This requires an openness from both players, but it's up to you to make the first step.
If you think I'm exaggerating, imagine a society where you're not allowed to ask for a direction. That's the same principle, just on another level. Let's take it to the next one.