High Risk and Likelihood of Risk

I often here the phrase:

"When you do something often the risk of it becomes higher than it usually is" - is this correct? So according to this analagy, if I cross a road once its risky, but if I cross the same road, say, 10 times, that risk is going to be higher?  I think what people (or me) often mix up is High Risk, is different to an Increased likelihood of risk.  I see the logic behind the quote - crossing the road multiple times will increase your likelihood of being hit by a car.

Now for example, say crossing a road is risked at Medium, and driving drunk is risked at Very High. Lets say the "risk" is being hit by a car (or anything else on the road)

So if I cross a road 10 times does that medium turn into High and and if I am driving drunk more than once does that risk become Immanent?

Something I need to get my head around...