Bruce Levin gave an excellent insight to what ultimately is a sure shot recipe for progress. Not taking risks in life is a sure shot symbol of stagnation and ultimately death. To be progressive, one needs to take risk and there is absolutely no debate about this. But yes, one should take calculated risks.
So ask yourself this everyday, what do you intend to do with your life? Where do you see yourself in the near future and some time off? Make your decisions accordingly.